PACE Final Lap (Organic Chemistry) PDF

GENERAL ORGANIC CHEMISTRY FINAL LAP - 2019
RESONANCE & AROMATICITY
Q.1 Which of the following statements is (are) true about resonance.

(a) Resonance is an intramolecular process.
(b) Resonance involves delocalization of both s and p electrons.
(c) Resonance involves delocalization of p electrons only.
(d) Resonance decreases potential energy of a molecule.
(e) Resonance has no effect on the potential energy of a molecule.
(f) Resonance is the only way to increase molecular stability.
(g) Resonance is not the only way to increase molecular stability.
(h) Any resonating molecule is always more stable than any nonresonating molecule.
(i) The canonical structure explains all features of a molecule.
(j) The resonance hybrid explains all features of a molecule.
(k) Resonating structures are real and resonance hybrid is imaginary.
(l) Resonance hybrid is real and resonating structures are imaginary.
(m) Resonance hybrid is always more stable than all canonical structures.
Q.2 Consider structural formulas A, B and C:
(A) (B) (C)

(a) Are A, B and C constitutional isomers, or are they resonance forms?
(b) Which structures have a negatively charged carbon?
(c) Which structures have a positively charged carbon?
(d) Which structures have a positively charged nitrogen?
(e) Which structures have a negatively charged nitrogen?
(f) What is the net charge on each structure?
(g) Which is a more stable structure, A or B? Why?
(h) Which is a more stable structure, B or C? Why?
Q.3 In each of the following pairs, determine whether the two represent resonance forms of a single species
or depict different substances. If two structures are not resonance froms, explain why.
(a) and
(b) and
(c) and
Q.4 Which of the following statement is incorrect ?

(A) Contributing structures contributes to the resonance hybrid in proportion of their energies.
(B) Equivalent contributing structure make the resonance very important.
(C) Contributing structures represent hypothetical molecules having no real existance.
(D) Contributing structures are less stable than the resonance hybrid.
CENTERS : MUMBAI / DELHI /AKOLA / LUCKNOW /NASHIK / PUNE / NAGPUR / BOKARO / DUBAI # 96
Q.5 Which one of the following pairs of structures does not represent the phenomenon of resonance?
O O¯
||  |
(A) H 2C  CH  C  H ; CH 2  CH  C  H
 
(B) CH 2  CH  CH Cl ; CH 2  CH  CH  Cl
O O¯
|| |
(C) (CH 3 ) 2 CH  C  O ¯ ; (CH 3 ) 2 CH  C  O
O O¯
|| |
(D) CH 3  CH 2  C  CH 3 ; CH 3  CH  C  CH 3
Q.6 In which of the following lone-pair indicated is involved in resonance :
(a) (b) (c) (d)

(e) CH2= CH – C H 2 (f) CH2 = CH – CH = N H
Q.7 In which of the following lone-pair indicated is not involved in resonance :

 
(a) CH2 = CH – N H – CH3 (b) CH2 = CH – CH = O

(c) CH2 = CH – O – CH = CH2 (d) CH2 = CH – C  N••

(e) (f)
Q.8 Which of the following is not a valid resonating structure of the other three?
+ + +
NH2 NH2 NH2 NH2
(i) (a) + (b) (c) (d)
  — 
(ii) (a) CH 2  N  O ¯ (b) CH 2  N  O ¯ (c) CH 2  N  O (d) CH 2  N  O
| | | |
CH 3 CH 3 CH 3 CH 3
Q.9 Draw the resonance forms to show the delocalization of charges in the following ions
O O
  +
(a) CH3 – C – CH2 (b) H – C – CH = CH – CH2 (c) CH2
(d) (e) O¯ (f) + NH (g)

+ O


(h) (i) CH3 – CH = CH – CH = CH – CH – CH3
O

(j) CH3 – CH = CH – CH = CH – CH 2
Q.10 Write stability order of following intermediates:

CH 3
  |
(i) (a) CH 3  CH 2 (b) CH 3  CH  CH 3 (c) CH 3  C 
|
CH 3
(ii) (a) + (b) + (c) +

 
(iii) (a) (b) (c)

(iv) (a) (b)  (c)

  

(v) (a) (b) (c) (d)
  
(vi) (a) CF3  CH 2 (b) CCl3  CH 2 (c) CBr3  CH 2

CH 3
  |
(i) (a) CH 3  CH 2 (b) CH 3  CH  CH 3 (c) CH 3  C 
|
CH 3

 
(ii) (a) (b) (c)

(iii) (a) (b)  (c)

  
(iv) (a) HC  C (b) CH2  CH (c) CH 3  CH 2
Q.12 Rank the following sets of intermediates in increasing order of their stability.
(i) (a) C6H5+ (b) p–NO2(C6H4)+ (c) p–CH3–(C6H4)+ (d) p–Cl–C6H4+
 
CH2 CH2 CH2
(ii) (a) (b) (c)
N OMe
O O
CH2 CH2 CH2

OH
(iii) (a) (b) (c)
OH
OH
  
(iv) (a) CF3  CH 2  CH 2 (b) CF3  CH 2 (c) CF3
 
(v) (a) CF3 (b) CCl3

CH 3
  |
(i) CH 3  CH 2 (b) CH 3  CH  CH 3 (c) CH 3  C 
|
CH 3
(ii) (a) (b) (c)
(iii) (a) (b) (c)
  
(iv) (a) HC  C (b) CH 2  CH (c) CH 3  CH 2
(v) (a) (b) (c)
Q.14 Among the following molecules, the correct order of C – C bond lenght is
(A) C2H6 > C2H4 > C6H6 > C2H2 (B) C2H6 > C6H6 > C2H4 > C2H2(C6H6 is benzene)
(C) C2H4 > C2H6 > C2H2 > C6H6 (D) C2H6 > C2H4 > C2H2 > C6H6
Q.15 Which of the following is (are) the correct order of bond lengths :
(A) C – C > C = C > C  C > C  N (B) C = N > C = O > C = C
(C) C = C > C = N > C = O (D) C – C > C = C > C º C > C – H
Q.16 C1 – C2 bond is shortest in
(A) (B) (C) (D)
Q.17 In which of the following resonance is possible

(A) CH2 = CH – CH2 – CHO (B) CH2 = CH – CH = O
(C) CH3COCH3 (D) CH2 = CH – CH2 – CH = CH2
Q.18 Which of the following compounds have delocalised electrons ?
(A) (B)
(C) CH3CH2NH CH2 CH = CH2 (D) CH2 = CH – CH2 – CH = CH2
Q.19 Compare the C–N bond-length in the following species:
(i) (ii) (iii)
Q.20 Which of the following species are conjugated ?
(A) (B)
:
(C) CH 2 = C = CH – NH 2 (D) All of these
Q.21 Which of the following example has both the resonating structure contributing equal to the resonance
hybrid
 
(A) CH3 – C – CH  CH – CH3  CH3 – C  CH – C H – CH3
| |
CH3 CH3
+
(B) CH3 – C – NH2  CH 3 – C = NH 2
|| |
O
O-
-
O O
(C) CH3 – C  CH3 – C
O- O
+ -
(D) CH2 = CH – CH = O  CH 2 – CH = CH – O
Q.22 In which of the following pairs, indicated bond having less bond dissociation energy :
(a) CH 3  CH 2  Br & CH 3  CH 2  Cl
 
(b) CH 3  CH  CH  Br & CH 3  CH  CH 3
 |
Br
(c) &
(d) &
(e) &
(f) &
Q.23 Discuss the following observations:

(a) C–Cl bond in vinyl chloride is stronger than in chloroethane.
(b) Carbon-carbon bond length in ethene is shorter than in CH2 = CHOCH3
(c) CH3SH is stronger acid than CH3OH
(d) CH3CH2NH2 is stronger base than CH2 = CHNH2.
Q.24 A canonical structure will be more stable if

(a) it has more number of p bonds than if it has less number of p bonds.
(b) the octets of all atoms are complete than if octets of all atoms are not complete.
(c) it involves cyclic delocalization of (4n + 2) p – electrons than if it involves acyclic delocalization of (4n +
2) p – electrons.
(d) it involves cyclic delocalization (4n) p – electrons than if it involves acyclic delocalizationof
(4n) p – electrons.
(e) +ve charge is on more electronegative atom than if +ve charge is on less electronegative atoms.
(f) –ve charge is on more electronegative atom than if –ve charge is on less electronegative atom.
Q.25 Resonance energy will be more if

(a) canonical structures are equivalent than if canonical structures are non-equivalent.
(b) molecule is aromatic than if molecule is not aromatic.
Q.26 In each set of species select the aromatic species.

+ +
(i) (a)  (b) (c) (d)
S
+ 
(ii) (a) (b) (c)  (d)
+   
(iii) (a) (b) (c) (d)

N
H
Q.27 Consider the given reaction:
+ 3H2 Pd /C
 
In the above reaction which one of the given ring will undergo reduction?
Br
Q.28 AgNO
 3  A
Select the correct statement about product A.

(A) Product is aromatic (B) Product has high dipole moment.
(C) Product has less resonance energy (D) Product is soluble in polar solvent.
Q.29 Which of the following is incorrectly orderd for resonance stability
(A)
(B)
(C) (I > II)
(D) (II = I)
Q.30 In which of the following pairs of resonating structures first resonating structure is more stable than
second.
(A)  (B)
(C)  (D) 
Q.31 Hyperconjugation is possible in
(A) (B) (C) (D)
Q.32 Which of the following molecule has longest C=C bond length.
(A) CH3–CH=CH–CH=CH–CH3 (B) CH2=CH–CH=CH2
(C) CH3–CH=CH–CH3 (D) CH2=CH2
Q.33 In which of the following molecule (s) , the resonance effect is present ?
(A) (B) (C) (D)
Q.34 Explain why which compound is aromatic, antiaromatic or nonaromatic.

H
+
(a) N (b) N S (c) (d)
O O O
isoxazole 1,3-thiazole pyran pyrylium ion
O NH2
N
(e) (f) (g)
O N N O
H
1,2-dihydropyridine H
-pyrone
cytosine
Q.35 Resonance is possible/s in

(A) CH2 = N H2 (B) CH3CH = C =
(C) (D)
Q.36 Which one of following represents different molecules?
(A) and (B) and
(C) and (D) and
 
CH2 CH2
(i) (a) (b)

F Cl

CH2
 CH2 
CH2
CH2
(ii) (a) (b) (c) (d)
Cl N CN
O O
 
(iii) (a) CH 2  CH (b) CH 2  CH 3
||
O
Q.38 In each of the following pairs of ions which ion is more stable:
 
(a) (I ) C6H5– CH 2 and (II) CH2=CH– CH 2
 
(b) (I) CH3– CH 2 and (II) CH2 = CH
(c) (I) and (II)
(d) (I) CH 3  CH  CH 3 and (II) CH 3  N  CH 3

| |
CH 3  C  CH 3 CH 3  C  CH 3
 
 
(e) CH2—CH=NH CH2=CH–NH
O¯ O¯
(f) +
CH3—C=CH–CH—CH3 CH3—C—CH=CH—CH3
+
O O O¯ O
(g) CH3—C–CH–C—CH3 CH3—C=CH–C—CH3
NH2 NH2
(h) +
CH3—CH2—C—NH2 CH3—CH2—C = NH2
+
Q.39 Select the least stable resonating structure in each of the following sets of carbocation.
O O
+ + +
(i) (a) CH2 = CH — N (b) CH2 – CH — N
O O
O O
+ + + +
(c) CH2 – CH — N (d) CH2 – CH = N
O O
 — — 
(ii) (a) CH 2  CH  CH  CH  NH 2 (b) CH 2  CH  CH  CH  NH 2
—  — 
(c) CH 2  CH  CH  CH  NH 2 (d) CH 2  CH  CH  CH  NH 2
   
(iii) (a) H 2 C — C H –CH = CH – O – CH3 (b) H 2 C — CH = CH – CH = O – CH3
   
(c) H2C = CH – CH – CH – O – CH3 (d) H2C = CH – C H – CH = O – CH3
(i) (a) (b) (c)
(ii) (a) (b)
 
CH2 CH2 CH2

H
(iii) (a) (b) H (c) C H
C H H
H
H C H
H
CH
2 CH CH2 CH2
2
(iv) (a) (b) (c) (d)

CH3 CH2Me CH Me2 CMe3
Me Ph +
| | 
(v) (a) Me  C  (b) Ph — C  (c) Ph – CH 2 (d)
| |
Me Ph
+
+
(vi) (a) (b) (c)
+
+
(d) (e)
+
Q.41 Which one of the following molecules has all the effect, namely inductive, mesomeric and hyperconjugative?
(A) CH3Cl (B) CH3–CH = CH2
(C) CH 3  CH  CH  C  CH 3 (D) CH2 = CH – CH = CH2
||
O
Q.42 Hyperconjugation is best described as:
(A) Delocalisation of p electrons into a nearby empty orbital.
(B) Delocalisation of s electrons into a nearby empty orbital.
(C) The effect of alkyl groups donating a small amount of electron density inductively into a carbocation.
(D) The migration of a carbon or hydrogen from one carbocation to another.
Q.43 Select the correct statement.

(i) Delocalisation of s-electron is hyperconjugation.
(ii) Delocalisation of p-electron is resonance.
(iii) Partial displacement of s-electron is inductive effect.
(A) i & iii (B) ii & iii (C) i & ii (D) i, ii, iii
Q.44 Arrange following compounds in decreasing order of electrophilic substitution.

CH3 CH3 H
CH3 H—C—CH3 CH3—C—CH3 H—C—CH3
(i) (ii) (iii) (iv)
(A) i > ii > iii > iv (B) iii > iv > ii > i (C) i > iv > ii > iii (D) i > ii > iv > iii
Q.45 Select correct statement:
(A) –NO2 and –COOH group deactivates benzene nucleus for attack of E+ at o– and p– sites.
(B) –NH2 and –OMe group activates benzene nucleous for attack of E+ at o– and p– sites.
(C) –NH2 and –COOH group activates benzene nucleous for attack of E+ at o– and p– sites.
(D) –NO2 and –OMe group activates benzene nucleous for attack of E+ at o– and p– sites.
Q.46 In which of the following pairs, indicated bond is of greater strength :
(a) and CH 2  CH 2 (b) CH3  C  CH and HC  CH

  
(c) and CH 3  CH 2  Cl

(d) CH 2  CH  CH  CH 2 and CH 2  CH 2  CH 2  CH 3
 
(e) CH 2  CH  CH  CH 2 and CH 2  CH  NO 2
 
(f) and
Q.47 Choose the more stable alkene in each of the following pairs. Explain your reasoning.
(a) 1-Methylcyclohexene or 3-methylcyclohexene
(b) Isopropenylcyclopentane or allylcyclopentane
(c) or
Q.48 Match each alkene with the appropriate heat of combustion:

Heats of combustion (kJ/mol) : 5293 ; 4658; 4650; 4638; 4632
(a) 1-Heptene (b) 2,4-Dimethyl-1-pentene
(c) 2,4-Dimethyl-2-pentene (d) 4,4-Dimethyl-2-pentene
(e) 2,4,4-Trimethyl-2-pentene
Q.49 Compare heat of hydrogenation (Decreasing order)
(i) &
(ii) &
(iii) &
CH3
(iv) CH2 = CH – CH & CH3 –CH = C
CH3
Q.50 Compare heat of hydrogenation (Decreasing order)
(i)
A B D
(ii)
Q.51 (I) Stability order and (II) heat of hydrogenation orders.
(a) (b) (c) (d)
Q.52 Among the following pairs identify the one which gives higher heat of hydrogenation :
(a) and
(b) and
(c) CH3 – CH = CH – CH3 and CH3 – CH2 – CH = CH2
(d) and
Q.53 Write increasing order of heat of hydrogenation (HOH):
(i) (a) (b)
(ii) (a) (b) (c) (d)
(iii) (a) (b) (c) (d) (e)
(iv) (a) (b) (c)
(v) (a) (b) (c) (Heat of hydrogenation per p bond)
(vi) (a) (b) (c) (HOH per benzene ring)
Q.54 Give decreasing order of heat of combustion (HOC):
(i) (a) (b) (c)
(ii) (a) (b) (c) (d)
(iii) (a) (b)
(iv) (a) (b) (c)
+
  
(i) (a) C (b) Ph  CH 2 (c) (d) Me  C Me
|
Me
 
(ii) (a) CH 2  CH (b) CH 2  CH  CH 2 (c) CH2 (d) CH3
CH2
CH2 CH2
(iii) (a) (b) (c)

Cl Cl
+ +
CH2 CH2 +
(iv) (a) (b) (c)
+ + +
(v) (a) (b) (c)
  
(vi) (a) (b) (c)
Q.1 (a), (c), (d), (g), (j), (l), (m)
Q.2 a = Resonance form, b= A, c = C, d= A & B, e=B&C, f = 0, g = B, h = B
Q.3 (a) is resonance form; (b) is not resonance form due to different number of l.p. and b.p.;
(c) is not resonance form due to different number of l.p. and b.p
Q.4 A Q.5 D Q.6 (b), (d), (e) Q.7 (b), (d), (e) Q.8 (i) a (ii) c
O¯ O¯
| |
Q.9 (a) CH 3  C  CH 2 (b) H  C  CH  CH  CH 2
+ +
CH2 CH2 CH2 CH2 CH2
+ +
(c)
+
(d) + (e) O¯ O O O
+
(f) NH (g) (h)
O+
O¯
 
(i) CH3  CH  CH  CH  CH  CH  CH3 (j) CH3  CH  CH  CH  CH  CH 2 ]
Q.10 (i) c>b>a (ii) b>c>a (iii) c>b>a (iv) b>c>a

(v) d>c > b>a (vi) a<b<c
Q.11 (i) a>b>c (ii) a>b>c (iii) a>c>b (iv) a>b>c
Q.12 (i) b < d < a < c (ii) b>c>a (iii) c>a>b (iv) c>a>b
(v) a>b
Q.13 (i) c>b>a (ii) c>b>a (iii) b>c>a (iv) c>b>a

(v) a>c>b
Q.14 B Q.15 A, C, D Q.16 D Q.17 B Q.18 B Q.19 iii > ii > i
Q.20 D Q.21 C
Q.22 (a) I, (b) II, (c) II, (d) I, (e) I, (f) I
—
Q.23 (a) Due to resonance C H 2 – CH = Cl+
(b) In CH2=CH–OCH3, there is single bond character due to resonance
—
C H 2 – CH = O+– CH3
(c) Conjugate base of CH3SH ie, CH3S is more stable than conjugate base of CH3OH, ie CH3O–
— 
(d) In CH2=CH–NH2 lone pair of N is delocalized C H 2 – CH = N H 2
Q.24 (a), (b), (c), (f) Q.25 (a), (b) Q.26 (i) a, b, d (ii) a, c (iii) b, c, d
Q.27 A Q.28 A, B, D Q.29 C
Q.30 C Q.31 A Q.32 A Q.33 A, D
Q.34 (a) A, (b) A, (c) N.A. (d) A, (e) A, (f) N.A. (g) A Q.35 A, B, C, D
Q.36 B
Q.37 (i) a< b (ii) b > c > a> d (iii) a> b
Q.38 (a) I, (b) I , (c) I I , (d) I I , (e) I I , (f) I, (g) II, (h) II Q.39 (i) c (ii) a (iii) c
Q.40 (i) a>b>c (ii) a>b (iii) c>a>b (iv) a>b>c>d

(v) d>b>a>c (vi) d>e>b>a>c
Q.41 C Q.42 B Q.43 D Q.44 C Q.45 A, B
Q.46 (a) II, (b) II, (c) I, (d) I, (e) II, (f) II Q.47 (a) i , (b) i , (c) ii
Q.48 (a) 4658, (b) 4638, (c) 4632, (d) 4650, (e) 5293 Q.49 (i) 2 > 1 (ii) 2 <1 (iii) 1 < 2 (iv) 1 > 2
Q.50 (i) D > C > B > A (ii) E > C > D > B > A Q.51 (I) d > c > b > a; (II) a > b > c > d
Q.52 (a) I, (b) I, (c) II, (d) I
Q.53 (i) b>a (ii) a>b>d>c (iii) a>b>c>d>e
(iv) b>c>a (v) a>b>c (vi) a>b>c
Q.54 (i) c > b > a (ii) a>b>c>d (iii) a>b (iv) c>b>a
Q.55 (i) a»c>d>b (ii) d>b>c>a (iii) b>a>c (iv) a>c>b
(v) b>c>a (vi) b>c>a
ACIDITY & BASICITY FINAL LAP - 2019
Q.1 Write correct order of acidic strength of following compounds:

(i) (a) H–F (b) H–Cl (c) H–Br (d) H–I
(ii) (a) CH4 (b) NH3 (c) H2O (d) H–F
CH3
(iii) (a) CH3–CH2–O–H (b) CH 3  CH  O  H (c) CH3–C–O–H
|
CH 3 CH3
(iv) (a) F–CH2–CH2–O–H (b) NO2–CH2–CH2–O–H


(c) Br–CH2–CH2–O–H (d) NH3  CH2  CH2  O  H

(i) (a) CH3COOH (b) CH3CH2OH (c) C6H5OH (d) C6H5SO3H
(ii) (a) (b) (c)

COOH COOH COOH
COOH COOH CH 2  COOH

(iii) (a) | (b) CH2 (c) |
COOH COOH CH 2  COOH
O O Cl O
|| || | ||
(i) (a) Cl  CH 2  C  O  H (b) Cl  CH  C  O  H (c) Cl  C  C  O  H
| |
Cl Cl
O O
|| ||
(ii) (a) CH 3  CH 2  CH  C  O  H (b) CH 3  CH  CH 2  C  O  H
| |
F F
O
||
(c) CH 2  CH 2  CH 2  C  O  H
|
F
O O
|| ||
(iii) (a) NO 2  CH 2  C  O  H (b) F  CH  C  O  H
2
O O
|| ||
(c) Ph  CH 2  C  O  H (d) CH 3  CH 2  C  O  H

O–H O–H O–H
(i) (a) (b) (c)
NO2 Cl CH3
O–H O–H O–H

Cl
(ii) (a) (b) (c)
Cl
Cl
O–H O–H O–H O–H
(iii) (a) (b) (c) (d)
O–H O O–H O–H O–H

N
(i) (a) O (b) O (c) (d)
N
O N
O O
O–H
O–H O–H O–H
O
N NO2 NO2 NO2
(ii) (a) (b) O (c) (d)
NO2
NO2 NO2

O O
C–O–H C–O–H
CH3
(i) (a) (b)
COOH COOH
Cl Br
(ii) (a) (b)
O
O O
C–O–H
C–O–H C–O–H
OMe
(iii) (a) (b) (c)
OMe OMe
O
C–O–H O O
C–O–H C–O–H
(iv) (a) (b) (c) NO2
N NO2
O O
Q.7 Select the strongest acid in each of the following sets :

OH OH OH OH
(i) (a) (b) (c) (d)
CH3 NO2 Cl NH2
OH OH OH OH
(ii) (a) (b) (c) (d)

NO2 F CH3
OH OH OH OH
OMe
(iii) (a) (b) (c) (d)
OMe
OMe
Q.8 Arrange the given phenols in their decreasing order of acidity:
(I) C6H5–OH (II) F OH
(III) Cl OH (IV) O2N OH

Select the correct answer from the given code:
(A) IV > III > I > II (B) IV > II > III > I (C) IV > III > II > I (D) IV > I > III > II
Q.9 Which one of the following is the most acidic?
(A) (B) (C) (D) CH2=CH–CH3
Q.10 Which one of the following phenols will show highest acidity?
(A) (B) (C) (D)
Q.11 Which of the following is weakest acid?
(A) (B) (C) (D)
Q.12 The correct pKa order of the follwoing acids is :

HO OH O HO OH
O O O O O O
(I) (II) (III)
(A) I > II > III (B) III > II > I (C) III > I > II (D) I > III > II
Q.13 Arrange pH of the given compounds in decreasing order:

(1) Phenol (2) Ethyl alcohol (3) Formic acid (4) Benzoic acid
(A) 1 > 2 > 3 > 4 (B) 2 > 1 > 4 > 3 (C)3 > 2 > 4 > 1 (D) 4 > 3 > 1 > 2
Q.14 Arrange acidity of given compounds in decreasing order:

(I) CH3–NH–CH2–CH2–OH (II) CH3–NH–CH2–CH2–CH2–OH

(III) (CH 3 )3 N  CH 2  CH 2  OH
(A) III > I > II (B) III > II > I (C) I > II > III (D) II > I > III
Q.15 Consider the following compound
O
(A) (B) (C) || (D)
CH 3CCOOH
Which of the above compounds reacts with NaHCO3 giving CO2
Q.16 Say which pka belong to which functional group in case of following amino acids :
(i) cysteine : 1.8, 8.3 & 10.8
(ii) glutamic acid : : 2.19, 4.25, 9.67
Q.17 Record the following sets of compounds according to increasing pKa ( = – log Ka)
(a) , , cyclohexane carboxylic acid.
(b) 1-butyne, 1-butene, butane

(c) Propanoic acid, 3-bromopropanoic acid, 2-nitropropanoic acid
(d) Phenol,o-nitrophenol, o-cresol
(e) Hexylamine, aniline, methylamine
Q.18 Explain which is a stronger acid.

O O
|| ||
(a) CH3CH3 & BrCH2NO2 (b) CH 3  C  CH 3 & CH 3  C  CH 2CN
(c) CH3 – CHO & CH3 – NO2
Q.19 Explain which is a weaker acid.

OH OH
(a) or (c) or
O=C–CH3 O=C–CH3
(b) or
Q.20 Which of the following would you predict to be the stronger acid ?
(a) or
(b) CH3 – CH2 – CH2 – OH or CH3 – CH = CH – OH

(c) CH3 – CH = CH – CH2 – OH or CH3 – CH = CH – OH
BASICITY
Q.1 Write increasing order of basic strength of following:
(i) (a) F  (b) Cl  (c) Br  (d) I 
(ii) (a) CH 3 (b) NH 2 (c) OH  (d) F 
(iii) (a) R–NH2 (b) Ph–NH2 (c) R  C  NH 2

||
O
(iv) (a) NH3 (b) MeNH2 (c) Me2NH (d) Me3N (Gas phase)
(v) (a) NH3 (b) MeNH2 (c) Me2NH (d) Me3N (in H2O)

O
(i) (a) (b) (c)
NH NH N
Me
NH2 NH2
(ii) (a) (b) (c)

NH
N N N
(iii) (a) (b) (c)
O2N Me F
NH2 NH2
NH2 NH2
(iv) (a) (b) (c) (d)


NH3 Cl CH 3 H

  
(i) (a) CH3–CH2– N H 2 (b) CH3–CH= NH (c) CH3–C N
        
(ii) (a) CH 3  C  NH 2 (b) CH3–CH2– NH 2 (c) CH 3  C  N H 2 (d) NH 2 C  N H 2
|| || ||
O N H N

H

NH2
(iii) (a) N (b) (c)

H N
O
NH2 NH–CH2–CH3
NH–C–CH3
(iv) (a) (b) (c)
NH2 NH2
Me Me
(v) (a) (b) Me Me

N N
O O O O
NH2 NH2 NH2 NH2
(i) (a) (b) (c) (d)

NO2 CN OMe NH2
NH2 NH2
NH2 H
C H
(ii) (a) (b) H (c)
H C H
H C
H H
H
NH2
NH2 NH2
NO2
(iii) (a) (b) (c)
NO2 NO2
NH2 NH2 H NH2

C H
(iv) (a) (b) (c)
H
NMe2 Me Me
NMe2 N
OMe
(v) (a) (b) (c)
OMe OMe
Q.5 Select the strongest base in following compound :

O S
(i) (a) (b) (c) (d)
N N N N
H H H
NH2
(ii) (a) (b) (c) (d)

NH N
N
H
N
(iii) (a) (b) (c) (d)
N N N N
H H CH3 H
H H Me
+
N¯Li N N N
(iv) (a) (b) (c) (d)
Q.6 Arrange the following compound in decreasing order of their basicity.

(i) (a) H2C = CHNa (b) CH3CH2Na (c) CH3CH2ONa (d) HC  CNa
(ii) (a) NH2 (b) CH2 – NH2 (c) NH2 (d) C – NH2
NO2 O
(iii) (a) HO¯ (b) NH3 (c) H2O
Q.7 Basicity order in following compound is :
CH3 CH3
O
Nb
H2N– C – CH2 CH2 – NH – C – CH3
c
NH
a
N
CH3 d CH3
(A) b > d > a > c (B) a > b > d > c (C) a > b > c > d (D) a > c > b > d
Q.8 Consider the following bases:

(I) o-nitroaniline (II) m-nitroaniline (III) p-nitroaniline
The decreasing order of basicity is:
(A) II > III > I (B) II > I > III (C) I > II >III (D) I > III > II
Q.9 Consider the basicity of the following aromatic amines:

(I) aniline (II) p-nitroaniline (III) p-methoxyaniline (IV) p-methylaniline
The correct order of decreasing basicity is:
(A) III > IV > I > II (B) III > IV > II > I
(C) I > II > III > IV (D) IV > III > II > I
Q.10 Which one of the following is least basic in character?
(A) (B) (C) (D)
Q.11 In each of the following pair of compounds, which is more basic in aqueous solution? Give an explanation
for your choice:
(a) CH3NH2 or CF3NH2 (b) CH3CONH2 or H2N NH2

(c) n-PrNH2 or CH3CN (d) C6H5N(CH3)2 or 2,6-dimethyl-N-N-dimethylaniline
(e) m-nitroaniline or p-nitroaniline
Q.12 From the following pair, select the stronger base:

(a) p-methoxy aniline or p-cyanoaniline (b) pyridine or pyrrole
(c) CH 3CN or CH3CH2NH2
Q.13 Choose the member of each of the following pairs of compunds that is likely to be the weaker base.
(a) H2O or H3O (b) H2S, HS–, S2– (c) Cl–, SH–
(d) F–, OH–, NH2–, CH 3 (e) HF, H2O, NH3 (f) OH–, SH–, SeH–
Q.14 Explain which compound is the weaker base.
(a) or (b) CH2 = CH – CH = CH – CH2– or CH2 = CH – CH2–
O O O O
|| || || ||
(c) O   C  C  OH or HO  C  C  OH (d) or
Q.15 Rank the following amines in increasing basic nature.
(a)
(i) (ii) (iii) (iv)
(b)
(i) (ii) (iii) (iv)

Q.16 Arrange the basic strength of the following compounds.
(a) OH – CH3COO– Cl–
(i) (ii) (iii)
(b) CH  C– CH2 = CH– CH3 CH2 –
(i) (ii) (iii)
(c) CH2 = CHCH2NH2 CH3CH2 CH2NH2 CH  C – CH2NH2
(i) (ii) (iii)
Q.17 Arrange the basic strength of the following compounds.
(a)
(i) (ii) (iii)
(b)
(i) (ii) (iii)

NH2 NH2 NH2
(c)
H3C O2N
(i) (ii) (iii)
Q.18 Arrange the following compounds in order of increasing basicity.

(a) CH3NH2, CH3 NH 3 , CH3NH— (b) CH3O—, CH3NH—, CH3 CH 2
(c) CH3CH = CH—, CH3CH2 CH 2 , CH3CC—
Q.19 Rank the amines in each set in order of increasing basicity.

H
NH2 NH2 N
(a)
H
H N
(b) N N
H H H
N N N N
(c)
Q.20
Pyrimidine Imidazole Purine

Among the following which statement(s) is/are ture:
(A) Both N of pyrimidine are of same basic strength
(B) In imidazole protonation takes places on N–3.
(C) Purine has 3 basic N.
(D) Pyrimidine imidazole and purine all are aromatic
ACIDITY
Q.1 (i) d>c>b>a (ii) d>c>b>a (iii) a > b > c (iv) d>b>a>c
Q.2 (i) d > a > c> b (ii) c > b > a (iii) a > b > c
Q.3 (i) c > b > a (ii) a > b > c (iii) a > b > c > d
Q.4 (i) a > b > c (ii) a > b > c (iii) d > b > c > a
Q.5 (i) c > a > b > d (ii) d > c > a > b Q.6 (i) b > a, (ii) b > a, (iii) c > b > a, (iv) c > a > b
Q.7 (i) b (ii) a (iii) b
Q.8 C Q.9 B Q.10 C Q.11 B Q.12 B Q.13 B Q.14 A
Q.15 A, B, C, D
Q.16 (i) cysteine : (ii) glutamic acid :
Q.17 (a) 3<2<1; (b) 1<2<3; (c) 3<2<1; (d) 2<1<3; (e) 2<3<1
Q.18 (a) 2; (b) 2; (c) 2 Q.19 (a) 2; (b) 2; (c) 2 Q.20 (a) 2; (b) 2; (c) 2
BASICITY
Q.1 (i) a > b > c > d (ii) a > b> c> d (iii) a > b> c (iv) a < b< c< d
(v) c > b> d> a
Q.2 (i) a < b < c (ii) c > a > b (iii) b > c> a (iv) c > d> b > a
Q.3 (i) a > b > c (ii) d > c > b > a (iii) b > c > a (iv) c > b > a
(v) b > a
Q.4 (i) d > c > b > a (ii) c > b > a (iii) b > a > c (iv) a > b > c
(v) c > a > b
Q.5 (i) d (ii) b (iii) a (iv) a
Q.6 (i) b > a > d > c (ii) b > a > c > d (iii) a > b > c
Q.7 B Q.8 A Q.9 A Q.10 A
Q.11 (a) i, (b) ii, (c) i, (d) ii, (e) i Q.12 (a) i, (b) i, (c) ii
Q.13 (a) 2; (b) 1; (c) 1; (d) 1; (e) 1; (f) 3 Q.14 (a) 2; (b) 1; (c) 2; (d) 2
Q.15 (a) 3<2<1<4; (b) 1<2<3<4 Q.16 (a) 1>2>3; (b) 1<2<3; (c) 3<1<2
Q.17 (a) 2<1<3; (b) 1<2<3; (c) 2 > 1 > 3 Q.18 (a) 2<1<3; (b) 1<2<3; (c) 3<1<2
Q.19 (a) 2 > 1> 3, (b) 1 > 2> 3, (c) 1 > 3 > 2, Q.20 A, B, C, D
ISOMERS FINAL LAP - 2019
Exercise-1
Q.1 Which will show geometrical isomerism.
(A) (B) (C) (D)
Q.2 Configuration of is
(A) R (B) S (C) D (D) L
Q.3 is diastereomers of
(A) (B) (C) (D)
Q.4 Give the correct order of initials T or F for following statements. Use T if statement is true and F if it is
false.
I. Me–CH=C=C=CH–Br is optically active.
II. All optically active compound are chiral.
III. All chiral pyramidal molecules are optically inactive.
IV CH3–CH2–CH2–COOH and CH 3  CH  CH 3 are positional isomers.
|
COOH
(A) TTTF (B) FTFT (C) FTFF (D) TFTT
Q.5 From the following four structures select:

(a) The optically active isomers (b) Optically inactive isomers
(c) Enantiomers pairs (d) Distereomer pairs
(I) (II) (III) (IV)
Q.6 Discuss the optical activity of the following two compounds and also label them as polar and non-polar.
(I) (II)
Q.7 Consider the following six structures:
(I) (II)
(III) (IV)
(V) (VI)
The stereochemical relationship between : (a) I and II, (b) III and IV, (c) II and III, (d) I and V, (e) IV and (VI)
Q.8 Indicate the stereo centres in the following molecule and total number of stereoisomers in the following
molecule.
Q.9 For each of the following pair, deduce the stereochemical relationship, i.e., whether they are enantiomers,
diastereomers or identical.
(a) and (b) and
(c) and
(d) and
Q.10 For each of the following molecules, indicate, whether they are chiral, achiral or meso compound:
(I) (II) (III) (IV)
(V) (VI) (VII)
Q.11 For each of the following pair of structures, indicate, if the compounds are identical, constitutional isomers,
enantiomers, distereomers, diffrerent.
(a) and (b) and
Q.12 How many stereoisomer may have this natural occuring compound.
(A) 8 (B) 16
(C) 64 (D) 128
Q.13 How many optically active stereoisomers are possible for butane-2, 3-diol
(A) 1 (B) 2 (C) 3 (D) 4
Q.14 Identify whether each of following pair of compounds are identical or enantiomers, diastereoisomer or
constitutional isomers.
(a) and (b) and
(c) and (d) and
(e) and (f) and
(g) (h)
(i) (j)
(k) (l)
(m) and (n) and
(o) and (p) and
Q.15 How many stereoisomers are possible for the molecule shown below:
Q.16 Discuss the type of isomerism exhibited by the following pairs:
(a) and
(b) and
(c) and
(d) CH3– CH2– CH2– CN and CH 3  CH  CH 3

|
CN
(e) and
Q.17 Draw resonance structure of the amides shown below and select them which are stereoisomeric:
(a) (b) (c)
(d)
Q.18 Which of following will exhibit geometrical isomerism?

(A) 1-phenyl-2-butene (B) 3-phenyl-1-butene
(C) 2-phenyl-1-butene (D) 1,1-diphenyl-1-propene
Q.19 How many optical isomers are possible for butane-2, 3-diol
(A) 1 (B) 2 (C) 3 (D) 4
Q.20 MeCH=CH–CH=C=CH–CH=CH2
Total number of geometrical isomers possible for above compounds are:
(A) 16 (B) 8 (C) 4 (D) 2
Q.21 total stereoisomers of the given compound is___________.
Q.22 Which point on the potential energy diagram in represented by Newmann projection shown?
Q.23 Truxillic acid can exist theretically in five stereosiomeric form all of which are known an optically inactive
explain,where a = – CO2H, b = – C6H5
Q.24 The most stable enol-form of compound is
(A) (B) (C) (D)
Q.25(a) A cyclobutandicarboxylic acid exist in two stereo-isomeric forms in which one is polar but non-resolvable
while other is non-polar but resolvable into enantiomers. Deduce structures of all these compounds.
(b) Select resolvable compounds.
(i) (ii) (iii) Ph  S  O

|
CH 3
(iv) (v) MeCHBrCH2Me (vi)

(vii) (viii) (ix) Me N DH 2 Br 
(x) MeCH 2 CHCH 2Me (xi) (xii) C=C=CH2

|
OH
Q.26 Which of the Newman projections shown below represents the most stable conformation about the
C1–C2 bond of 1-iodo-2-methyl propane?
(A) (B) (C) (D)
Q.27 Select the pair of enantiomer and diastereomers out of the following:
Q.28 In each of the following molecules, indicate the presence of a centre of chirality with an asterisk (*)
(a) (b) (c) (d) (e)
Q.29 Choose the correct option for the following molecule in view of chemical bonding
(A) non-planar (B)   0 (C) A & B both (D)  = 0
Q.30 Match the column-I with column-II. Note that column-I may have more than one matching options
in column-II.
Column–I (stability) Column-II (Reason)
(A) > CH 3 (P) Inductive effect
(B) < CH 3– (Q) Resonance
(C) > H3C– CH 2 (R) Hyperconjugation
(D) > (S) steric hindrance
Q.31
is dimethyl derivative of a compound 'A' and is fairly stable but most of the molecules of 'A'
gets converted into another compound 'B' on keeping. What are the structures of 'A' and 'B'. Explain the
reason of conversion A into B.
Exercise-2
1. Which of the following are isomers
(A) I, II only (B) III, IV only (C) I, II, III (D) All
2. No. of functional groups present in the following compound is :
(A) 5 (B) 7 (C) 6 (D) 8
3. Quinine is the most important alkaloid obtained from cinchona bark. It’s molecular formula is C20H24N2O2. It
may contain
(A) 5 double bond & 6 ring (B) 6 double bond & 4 ring
(C) 6 double bond & 3 ring (D) 7 double bond & 5 ring
4. In the structure of 4-Isopropyl-2,4,5-trimethylheptane, number of 10, 20 & 30 H’s are respectively

(A) 18, 5, 4 (B) 21, 4, 3 (C) 18, 4, 3 (D) 21, 5, 4
5. How many 1° amines are possiple for the molecular formula C7H9N which contain benzene ring also
(A) 1 (B) 4 (C) 3 (D) 2
6. Find out the total number of geometrical isomers of the following compound
(CH3)CH = C = C(CH3)(C2H5)
(A) 0 (B) 2 (C) 3 (D) 4
7. Which of the following will not show geometrical isomerism
(A) (B) (C) (D)
CH3
8. How many products are formed by monochlorination of .

CH3
CH
H3C CH3
(A) 13 (B) 12 (C) 15 (D) 14
9. Which will show geometrical isomerism

CHCH3 CHCH3
CH2 CHCH3 CH3
(A) CH3 (B) CH3 (C) (D)
10. How many stereoisomers are possible for Gorlic acid (C18H30O2)
CH=CH
CH(CH2)6CH=CH(CH2)4COOH
CH2-CH2
(A) 6 (B) 4 (C) 8 (D) 2
11. Molecular formula of Anthanthrone is
O
(A) C22H8O2 (B) C21H10O2 (C) C23H10O2 (D) C22H10O2
=
= =
12. = How many geometrical isomers the above compound will posses
O
(A) 2(4-3/2) (B) 26 (C) 25-22 (D) 25
13. Structure of Biotin, (C10H16N2O3S) is as follows
No. of chiral carbon & D.U. (degree of unsaturation) for Biotin are
(A) 4,3 (B) 3,3 (C) 4,4 (D) 3,4
14. Which of the following pairs are nonsuperimposable over each other ?
CH3 CH3
I H OH HO H
C2H5 C2H5
II CH3-O-CH3 CH3-CH2-OH
III
IV CH3-CH2-CHO CH3-CH2-CH2-CHO
V and
(A) I, II, III, IV (B) I, V (C) I, II, III (D) I, II, IV
15. Which statement is correct about the following structures
CH3 C2H5 Cl
H Br H Br H3CO C2H5
Cl OCH3 H3CO Cl H Br
C2H5 CH3 CH3
I II III
(A) I & III are structural isomers
(B) I & II & I & III are enantiomers
(C) I, III are enantiomers and I, II are structural isomers
(D) I, II & III are stereoisomers
16. Indicate the number of chiral carbon atoms in the following molecule.
HO
(A) 6 (B) 7 (C) 8 (D) 9
17. 3, 5-Dimethylcyclohexanol has total stereoisomers

(A) 3 (B) 4 (C) 8 (D) 12
18. 2, 4-Dimethylcyclohexanol has total stereoisomers

(A) 4 (B) 3 (C) 8 (D) 12
19. In the number of stereoisomers are
(A) 26 (B) 25 (C) 24 (D) 23
2 Br
20. Ph – CH2 – CH2 – COOH 
  PhCH2CHBrCOOH
Re d P
The product is
(A) racemic mixture (B) pure (+) (C) pure (–) (D) none of these
21. and are
(A) enantiomers (B) diastereomers (C) mesomers (D) all of these
22. can have
(A) geometrical isomer (B) optical isomers (C) epimer (D) none of these
23.
Which is more stable

(A) A > B (B) A = B (C) A < B (D) none
24. In the given conformation shown below
orientation of I and Br atoms are

(A) (a, e) (B) (e, e) (C) (e, a) (D) (a, a)
25. In the above conformation Br, Et are (geometrical relationship)

(A) cis (B) trans (C) both (D) none of these
26. In the above conformation Me, Et are

(A) trans (B) cis (C) both (D) none of these
27. Between &
(A) I is more stable than II (B) II is more stable than I

(C) I & II are equally stable (D) can’t say about their relative stability
28. 1-Bromo-2-chlorocyclohexane has several conformations. The stablest one has

(A) (1e – Br, 2e – Cl) (B) (1e – Br, 2a – Cl) (C) (1a – Br, 2a – Cl) (D) (1a – Br, 2e – Cl)
29. Among the 1, 3-dibromo cyclohexane conformations, the stablest one is

(A) (1a – Br, 3a – Br) (B) (1e – Br, 3e – Br) (C) (1a – Br, 3e – Br) (D) (1e – Br, 3a – Br)
30.
Between I, II the stable one is

(A) I (B) II (C) equally stable (D) none of these
31. Between and the stable one is
(A) I (B) II (C) both are equally stable (D) can’t be predicted
32. is
(A) optically active (B) optically inactive (C) meso in nature (D) none of these
33. and are
(A) diastereomers (B) conformational enantiomers

(C) configurational enantiomers (D) racemic form
34. Between and the relationship is
(A) conformational enantiomer (B) identical

(C) conformational diastereomer (D) none of these
35. and are
(A) enantiomers (B) identical (C) optically inactive (D) all of these
36. The compound
(A) is opticaly acitve (B) is a meso compound

(C) has zero dipole moment (D) has all groups in cis form
37. Which name is correct for
(A) cis-(a)-2-Decalol (B) cis-(e)-2-Decalol (C) trans-(a)-2-decalol (D) trans-(e)-2-Decalol
38.
Select the correct statement/s

(A) All are identical compounds (B) III and IV are identical and meso compounds
(C) I and II are optically active compounds
(D) I and II are configurational isomers while II and IV are conformational isomers
39. Draw the most stable conformation of 1-Chloropropane. W hich statement is correct about this
conformation.
(A) It is the most polar form (B) It has maximum torsional strain
(C) It has minimum steric strain (D) A and C both
40. The optically active alkyl chloride is
(A) (B) (C) (D)
41. Compound A (C6H12) does not absorb H2 in presence of Ni. It forms two monochloro isomers on photochemi-
cal chlorination. Its structure can be
(A) (B) (C) (D)
42. Which of the following molecule/s is / are chiral :
(A) CH3H2C  N  CH3 (B) (C) (D)

|
CH2  CH2  CH3
I II III IV
(A) I (B) I, II (C) III, IV (D) All
43. Which of the following species will be optically active :

C 2H5
|
(A) (B) H3 C  N  C 3H7
(C) (D)
44. How many spatial orientations are possible in the following compound ?
(A) 2 (B) 4 (C) 6 (D) 8
CH2OH
|
45. HO  C  H represents the Fischer projection formula :
|
CHO
(A) D (B) L (C) d (D) l
46. Hydrogenation of the adjoining compound in the presence of poisoned palladium catalyst gives.
(A) an optically active compound (B) an optically inactive compound

(C) a racemic mixture (D) a diastereomeric mixture
47. Mention the relationship between compounds of following pairs (isomers (type), Homologs, identicals)
(I) (II)
(A)
(B)
(C)
(D)
(E)
48. Which of the following is a meso isomer,
(A) (B) (C) (D)
49. How many optically active products can be formed in the following reaction
(A) 2 (B) 4 (C) 6 (D) 8
50. Which of the following compound has zero dipole moment in one of the stable conformations
(A) HO – CH2 – CH2 – OH (B) CH3 – CHCl – CHBr – CH3
(C) d-CH3 – CHCl – CHCl – CH3 (D) meso-CH3 – CHCl – CHCl – CH3
51. Which of the following are identical compounds
(A) I, II (B) I, III (C) I, IV (D) II, III
52. The following two compounds are
(A) conformational isomers (B) optical isomers

(C) structural isomers (D) identical compounds
53. Establish the relationship between the following pairs, as enantiomers, identicals, diastereomers or struc-
tural isomers.
(i) (ii)
(iii) (iv)
54. Observe the structures of compounds A, B, C and D. Write the relationship between the given pairs of
compounds.
(I) A and B are .......... (II) A and C are ............

(III) A and D are ......... (IV) C and D are ..........
55. Compounds with molecular formula C2H7N can be

(A) Functional isomers and metamers (B) Only functional isomers
(C) Functional and positional isomers (D) Chain, positional, functional and metamers
56. Total number of isomers having molecular formula C3H4O and only functional group can be,
(A) 1 (B) 2 (C) 3 (D) 4
57. How many products are formed by monochlorination of (Ignore stereoisomers)
(A) 4 (B) 2 (C) 5 (D) 3
58. The total number of 4° (quaternary) carbon atoms present in cholestanol is
(A) 3 (B) 8 (C) 4 (D) 2
59. Total number of phenol isomers of the compound C8H10O is

(A) 10 (B) 9 (C) 8 (D) 6
60. The following two compounds I and II are ...................... isomers.
and
(A) Geometrical (B) Geometrical and positional

(C) Positional (D) Geometrical, optical and positional
61. Which of the following will not show geometrical isomerism
(A) (B) (C) (D)
62. Fill the correct type of isomerism

(A) CH3 – CH2 – CH2 – CH2 – NH2 (B) CH3 – CH2 – NH – CH2 – CH3
(C) CH3 – CH2 – N – CH3 (D) CH3 – CH2 – CH2 – NH – CH3
CH3
(E) CH3 – CH2 – CH – NH2
CH3
(i) A & B are__________ (ii) B & C are__________
(iii) A & C are__________ (iv) B & D are__________
(v) A & E are__________ (vi) C & E are__________
63. For molecular formula C5H10 :

x  Total number of possible structural isomers.
y  How many of them can show geometrical isomerism.
(A) 10, 2 (B) 9, 2 (C) 9, 1 (D) 8, 4
64. Which of the following carbonyl compound will give two product after reaction with NH2OH :
(1) (2) (3) (4)
(5) (6) (7)
(A) 2, 3 , 4, 5, 6, 7 (B) 1, 2, 3, 5, 6, 7 (C) 2, 3, 4, 5, 6 (D) 1, 3, 4, 6, 7
65. Which of the following will show geometrical isomerism.
(1) (2)
(3) (4)
(5) (6)
(A) 1, 2, 3 (B) 1, 2, 5 (C) 1, 2, 4 (D) 3, 5, 6
66.
Incorrect statement for the above structure :
(A) I, II & III have CnH2n-2 general formula (B) I , II & III have same empirical formula
(C) I, II & III have same molecular formula (D) I , II are identical and homologue of compound III.
67. Which of the following will show geometical isomer.
(A) (B) (C) (D)
68. Total number of geometrical isomers in the following compound,
Ph–CH=CH– –CH2–CH= –OH
(A) 2 (B) 4 (C) 8 (D) 16
69. Which of the following will not show geometrical isomerism.
(1) (2) (3)
(4) (5) (6)
(7) (8) (9)
(10) (11) (12) = CH – CH = CH – Ph
(13) (14)
(A) 1, 2, 5, 6, 8, 9, 14 (B) 3, 6, 7, 8, 9, 11, 14 (C) 3, 6, 10, 11, 12, 13

(D) Except 2, 10, 13
70. Which of the following is pair of geometrical isomerism :
(A) and
(B) and
(C) and
(D) and
71. Write down total number of geometrical isomers after reaction with NH2OH.
(1)
(2)
72. Indicate the type of isomers for the following compounds :
(i) (ii)
(iii) (iv)
(v) (vi)
(vii)
73. In which option all compounds can show geometrical isomerism.
(A)
(B) , C2FClBrI.
(C) , Ph – CH = N – OH, Ph2N2
(D) CH3–CH = N–OH , H2C = CH–CH = CH–CN.
74. Consider the following four statements

S1 : Geometrical isomers are not mirror image isomer.
S2 : A compound having double bond (restricted bond) always show geometrical isomerism
S3 : Acyclic compounds having single bond does not show geometrical isomerism
S4 : Cyclodecene can exist in cis & trans form
(A) T F F T (B) T T F T (C) F F F T (D) T F T T
75. Which will not show geometrical isomerism
(A) (B) (C) ClCH = CHCl (D) Ph—N=N—Ph
76. Which of the following compound posses plane of symmetry -
(A) (B) (C) (D)
77. Which of the following compounds are optically active ?
(A) (B) (C) (D)
78. Well known pain killer Nurofen is an ibuprofen how many stereoisomers it would have ?
If we have a racemic mixture of ibuprofen which one of the following can be used to resolve the isomers.
Ph D
| |
(A) 4, CH3 – CH2 – OH (B) 8, CH3  C  OH (C) 4, CH3  C  OH (D) 8, CH3 – CH2 – OH
| |
Ph Ph
79. Which of the following pairs can be separated by fractional distillation :
Me NH Me NH Me
H
(A) H NH H and Me NH H
O O
COOH OH
H OH HOOC H
(B) H OH and HO COOH
COOH H
O O
(C) CH3–C–O–C3H7 and CH3–O–C–C2H5
H H H H
COOH COOH
(D) NH2 and CH3
CH3 CH3
CH3 NH2
80. Arrange following in decreasing order of percantage enol content.
(i) (ii) (iii) (iv)
(A) I > II > III > IV (B) II > I > III > IV (C) II > III > I > IV (D) III > II > IV > I
O
Ph || Ph - Fractional
OH / H2O distillation
81. Number of isomeric products (m) Number of fractions (n)
CH3 H
values of (m) and (n) are
(A) 2, 1 (B) 1, 1 (C) 2, 2 (D) 1, 2
82. Which of the following statement is/are correct about below newmann projection :
(A) I and II are functional isomers. (B) II and III are functional isomers
(C) II and III are metamers (D) I and III are metamers
Exercise-1
Q.1 (A, B, C) Q.2 (A, C) Q.3 (D)
Q.4 (C)
(II) Cyclic chiral pyramidal molecules are optically active.
(IV) CH3–CH2–CH2–COOH and CH 3  CH  CH 3 are chain isomers.
|
COOH
Q.5 (a) II and IV are chiral, hence optically active, (b) I and III are achiral, posses plane of symmetry, hence
optically inactive, (c) There is no enantiomer pair, both II and IV are identical structure, (d) I and II, II
and III, I and III are pair of distereomers.
Q.6 Compound I is optically inactive since it contain a plane of symmetry. Compound II is enantiomeric since
it does not contain plane of symmetry, hence chiral. Also compound I is polar while II is non polar.]
Q.7 (a) Both I and II are optically, but they are not mirror image of one another, hence, they are distereomers
(b) Distereomers ,(c) Enantiomers,(d) I and V are enantiomers,
(e) IV and VI are distereomers]
Q.8 [8] Q.9 (a) Enantiomers, (b) Identical, (c) Identical, (d) Identical]
Q.10 (I) Achiral, (II) Achiral, (III) Meso, (IV) Meso, (V) Meso, (VI) Chiral, (VII) Chiral
Q.11 (a) Distereomers, (b) Identical and meso
Q.12 (C) Q.13 (B)
Q.14 (a) Enantiomer, (b) Constitutional, (c) Constitutional, (d) Identical, (e) Identical,
(f) Diastereomer, (g) Identical, (h) Enantiomer, (i) Enantiomer, (j) Enantiomer,
(k) Diastereomer, (l) Identical, (m) Enantiomer, (n) Enantiomer, (o) Enatiomer, (p) Identical
Q.15 This compound has two chiral carbon, and a double bond capable of showing geometrical isomerism
giving rise to total eight different configurations possible for the molecule as shown below:
Q.16 (a) Both are similar structures, (b) They are positional isomers, (c) They are enantiomers, (d) chain ,
(e) Metamers
Q.17 (a)
(b)
(c)
(d) ]
Q.18 (A) Q.19 (C) Q.20 (D)
Q.21 [4] Q.22 [B]
Q.23 All isomer contain symmetry] Q.24 (D)
Q.25(a) The compound must be 1,2-cyclobutan-dicarboxylic acid since all other constitutional isomers are
non-resovable.
(b) (i) R, (ii) R, (iii) R, (iv) R, (v) R, (vi) R, (vii) N.R, (viii) R, (ix) N.R, (x) N. R., (xi) N.R. (xii) N.R
Q.26 (C)
Q.27 Enantiomer  (A,B) (C,D); Diastereomer (A,C)(A,D);(B,C)(B,D)
Q.29 (D) Q.30 (A) P,Q,R; (B) P; (C) P, R; (D) Q
Q.31 A is and it tautomerise into B as it is more stable because it is aromatic compound
B is
Exercise-2
1. (C) 2. (C) 3. (B) 4. (B)
5. (B) 6. (A) 7. (A) 8. (D)
9. (B, D) 10. (B) 11. (D) 12. (D)
13. (D) 14. (A) 15. (C) 16. (C)
17. (B) 18. (C) 19. (C) 20. (A)
21. (B) 22. (B) 23. (C) 24. (A)
25. (B) 26. (B) 27. (A) 28. (A)
29. (B) 30. (B) 31. (A) 32. (A)
33. (B) 34. (C) 35. (B) 36. (B)
37. (C) 38. (B, C) 39. (D) 40. (C, D)
41. (C) 42. (C) 43. (C) 44. (D)
45. (A) 46. (B)
47. (A) Chain isomer

(B) Metamers
(C) Metamers
(D) Metamers
(E) Homologs
48. (B) 49. (C) 50. (D) 51. (D)
52. (C)
53. (i) Identical (ii) Structural (positional) isomers (iii) Identical (iv) Identical
54. (I) Functional isomers (II) Homologs
(III) Homologs (IV) Metamers
55. (B) 56. (C) 57. (D) 58. (D)
59. (B) 60. (C) 61. (D)
62. Functional isomer Functional isomer

Functional isomer Metamer
Position isomer
63. (A) 10, 2

C C
| |
(1) C = C – C – C – C (2) C – C = C – C – C (3) C  C – C – C (4) C  C – C – C
C
(5) | (6) (7) (8) (9) (10)
C–C  C–C
64. (C) 65. (D) 66. (D) 67. (A, C)
68. (C) 69. (B) (B)
70. (A, B, D)
71. 8, 16
72. (i) Functional isomers (ii) Functional isomers (iii) Position isomers (iv) Functional isomers
(v) Position isomers (vi) Chain isomers (vii) Position isomers
73. (D) 74. (D) 75. (A) 76. (C)
77. (D) 78. (C) 79. (C)
80. (A, C) 81. (A) 82. (C) 83. (A, C)
REACTION MECHANISM FINAL LAP - 2019
Write the structure of more stable rearranged form of the following carbocations:
 +
(1) CH3CH2CH2+ (2) (CH 3 ) 2 CH CHCH 3 (3) (CH3 )3 CCHCH3
(4) (CH3CH2)3CCH2+ (5) (6)
 +
(7) C H 2  CH 2  CH 2 (8) (9)
|
CH 3  CH 2  O
H CH3 CH3

| |  |
(10) (11) CH3  C C  CH3 (12) CH2  C  C  C H  CH  CH3
| | | |
CH3 OH CH3 CH3
(13) (14) (15)
CH3 CH3
| |
(16) CH3  C  C  CH3 (17) (18) (19)
 |
OH

(20) CH3  CH  CH  C H2 (21) (22) (23)
(24) (25) (26) (27) (28)
(29) (30) (31) (32)
REACTION MECHANISM FINAL LAP - 2019

CH 3  CH 2  CH
(6) (7) | (8)
CH 3  CH 2  O
H CH3 CH3
|   | |
(10) (11) CH3  C  C  CH3 (12) CH2  C  C  CH  CH  CH3
| | | |
CH3 OH CH3 CH3
(13) (14) (15)
(16) (17) (18) (19)

(20) CH3  C H  CH  CH2 (21) (22)

(23) CH3  C  O (24) (25) (26)
(27) (28) (29)
(30) (31) (32)
REACTION INTERMEDIATES FINAL LAP - 2019
EXERCISE-I
Q.1 2-chloropentane on halogenation with chlorine gives 2,3, dichloropentane. What will be the structure of
free radical species formed in the reaction?
(A) Planar (B) Trigonal planar (C) Square planar (D) Pyramidal
Q.2 The correct order of rate of Wurtz recation.

Na
(I) CH2–F ether
 CH2–CH2
Na
(II) CH2–Cl ether
 CH2–CH2
Na
(III) CH2–Br ether
 CH2–CH2
Na
(IV) CH2–I ether
 CH2–CH2
(A) I > II > III > IV (B) II > I > III > IV
(C) IV > III > II > I (D) In all rate of Wurtz reaction is same
CH 3  CH  CO 2 K
electrolys
Q.3 is
|     (A) (Major)
CH 3  CH  CO 2 K
Major product (A) of above reaction

(A) (B) (C) (D)
Q.4 Consider the following reaction –

O
FeSO 4  H 2 O 2
Na
/ether
 Fenton
   P
OEt liq . NH 3 's
reagent
the major product P is:
O OH O O
(A) (B)
H H
O O
(C) O (D) OH
Q.5 NBS
  Na /
ether
 (X)
CCl .Peroxide
4
X is
(A) (B)
(C) (D) None of these
Q.6 Find out the correct order of rate of reaction towards allylic substitution.
CH 3
|
(I) CH3–CH = CH2 (II) CH3–CH2–CH=CH2 (III) CH 3  CH  CH  CH 2
(A) I > II > III (B) II > I > III
(C) III > II > I (D) III > I > II
Q.7 What will be the major product, when 2-methyl butane undergoes bromination in presence of light?
(A) 1-bromo-2-methyl butane
(B) 2-bromo-2-methyl butane
(C) 2-bromo-3-methyl butane
(D) 1-bromo-3-methyl butane
Q.8 Which can not be the possible product of the given reaction
Br
CH 3  CH 2  C  OAg 2 
CCl4 ,  product(s)
||
O
(A) CH3 – CH2 – Br (B) CH 3  CH 2  C  O  CH 2  CH 3

||
O
(C) CH3 – CH2 – CH2 – CH3 (D) CH3 – CH2 – CH3
Q.9 Pick the correct statement for monochlorination of R-secbutyl Bromide.
Me
Cl
Br 2
H 
300C
Et
(A) There are five possible product ; four are optically active one is optically inactive
(B) There are five possible product ; three are optically inactive & two are optically active
(C) There are five possible product ; two are optically inactive & three are optically active
(D) None of these
Q.10 Correct order of rate of photochlorination for following compounds is:
CH 3
|
CH3–CH3 CD3–CD3 CH 3  C  CH 3
|
CH 3
(I) (II) (III)

(A) II < I < III (B) I < II < III (C) III < I < II (D) II < III < I
Q.11 NBS
 Allylic brominated products
CCl 4 ,
Find out the incorrect statement.

(A) It gives total 9 allylic brominated products
(B) All allylic brominated products are optically active
(C) Substrate has 7 allylic hydrogens
(D) NBS gives Br2 constantly to reaction mixture.
Q.12 Which of the following carbocation is most stable?
(A) (B)
(C) (D)
Q.13 Which carbocation is least likely to form as an intermediate?
 
(A) (C6 H 5 )3 C (B) (C) (D) CH 2  CH
Q.14 For the reactions
(I)  + Clr , H1o (II)  + Clr , H o2

(III)  + Cl , H3o (IV)  + Cl , H o4
The correct decreasing order of enthalpies of reaction for producing carbocation is

(A) H1o > H o2 > H3o > H o4 (B) H o4 > H1o > H o2 > H3o
(C) H3o > H o2 > H1o > H o4 (D) H o2 > H1o > H o4 > H3o
Br
Q.15 , which is not the correct statement
(I)
(A) I is more soluble than bromocyclopropane
(B) I gives pale yellow ppt. on addition with A gNO3
(C) I is having lower dipole moment than bromocyclopropane
(D) I is more ionic than
Q.16 Which one of the following carbocation would you expect to rearrange.

(A) (B) (C) (D)
Q.17 How many 1,2-Shifts are involved during the course of following reaction:


(A) 1 (B) 2 (C) 3 (D) 4
Q.18 How many 1,2-Shifts are involved during the course of following reaction:
conc . H SO
 24 
(A) 1 (B) 2 (C) 3 (D) 4

Q.19 H (X).

Product (X) is
(A) (B) (C) (D)
Q.20 Among the given compounds, the correct dehydration order is:
(I) (II) (III) (IV)
(A) I < II < III < IV (B) II < III < IV < I
(C) I < III < IV < II (D) I < II < III = IV

Q.21 H P. The product P is:
5 C
(A) (B) (C) (D)
Q.22 Rate of dehydration when given compounds are treated with conc. H2SO4.
(P) (Q) (R) (S)
(A) P > Q > R > S (B) Q > P > R > S (C) R > Q > P > S (D) R > Q > S > P
2 H SO
Q.23  4  X


X is
(A) (B) (C) (D)

Q.24 H major product is

(A) (B) (C) (D)
H O
Q.25 3
  A, A is
(A) (B) (C) (D)

Q.26 H

(A) (B) (C) (D)
Conc . H SO
2
Q.27    4  A.

Product A is:
(A) (B) (C) (D)
Q.28 How many products are obtained in the given reaction :

Et Ph CH3 Ph
H SO
HO OH + HO OH 2 4 

Et Ph CH3 Ph
(A) 1 (B) 2 (C) 3 (D) 4
Q.29 Which of the following is not correct about P2.
O

Mg
 P H
 P2
H O 1
2 
(A) It is a spiro compound (B) It is a Ketone

(C) It can show tautomerism (D) It is an alkene
CH 3
|
Q.30 CH 3  CH — C — CH 2  NH 2 HNO
2  (X) (major)
| |
CH 3 CH 3
Major product of above reaction is
(A) (B)
(C) (D)
Q.31 Which will dehydrate at fastest rate by H3PO4:-

(A) 2-methyl butane-2-ol (B) 3-methyl butane-2-ol
(C) Butane-1-ol (D) 2-methyl butane-1-ol
Q.32 What is the order of reactivity with HBr.
(a) (b) (c)
(A) a > b > c (B) b > a > c

(C) c > b > a (D) b > c > a
CH = CH3
Q.33 HBr

H D CCl4
CH3
What is stereochemistry of product?

(A) Racemic mixture (B) Optically inactive
(C) Diastereomers (D) Meso product
Q.34 In the given reaction:
Br2
 [X]

[X] is:
(A) (B) (C) (D)
Q.35 Select the incorrect statement about the product mixture in the following reaction :
Br
2  Products
CCl 4
(A) it is optically active (B) it is racemic mixture

(C) it is a resolvable mixture (D) it is a mixture of erythro compounds
EXERCISE-II
Q.1 Which of the following can be produced by Wurtz reaction in good yield.
(A) (B) (C) (D)
Q.2 Select true statement(s):

(A) Instead of radical substitution, cyclopropane undergoes electrophilic addition reactions in sun light.
(B) In general, bromination is more selective than chlorination.
(C) The 2,4,6-tri-tert, butylphenoxy radical is resistant to dimerization.
(D) The radical-catalysed chlorination, ArCH3 ArCH2Cl, occurs faster when Ar = phenyl than when
Ar = p-nitrophenyl.
Q.3 Choose all alkane that give only one monochloro derivative upon reaction with chlorine in sun light.
(A) (B) (C) (D)
Q.4 NBS
 HBr
 (X) + (Y) enantiomeric pair
CCl / h
4
Br Br
(A) (B) (C) (D)

Br Br
Q.5 Select correct statement about the product (P) of the reaction:
Br
2 /
CCl4
 P
(A) P is optically inactive due to internal compensation

(B) P is optically inactive due to the presence of plane of symmetry in the molecule
(C) The structure of P can have three optical isomers possible.
(D) P can have four possible optical isomers.
Q.6 Products formed when HCl adds to 2,4- hexadiene is:
(A) 4-chloro-2-hexene (B) 2-chloro-3-hexene
(C) 2-chloro-4-hexene (D) 1-chloro-2-hexene
Q.7 In the given reaction
C7H12 (A) HBr


(A) can be
(A) (B) (C) (D)
Q.8 Which of following reaction product are diastereomer of each other.
Br
(
i ) NaCN
(A) 2
 (B) 
CCl 4 (ii ) H 
(C) HBr
 (D) CH 3  CH  CH  CH  Ph HCl

CCl4 peroxide
|
Et
Q.9 Which of the following can be formed during this reaction?

H
3O

OH
OH
(A) (B) (C) (D)

OH O O
OH
Q.10 Each of the compounds in column A is subjected to further chlorination. Match the following for them.
Column A Column B
(A) CHCl2–CH2–CH3 (P) Optically active original compound
(B) CH2Cl–CHCl–CH3 (Q) Only one trichloro product
(C) CH2Cl–CH2–CH2–Cl (R) Three trichloro product.
(D) CH3–CCl2–CH3 (S) Four trichloro product

Cl Cl
(E) | | (T) Atleast one of the trichloro product is
CH 3  C — C  CH 3 optically active.
| |
CH 3 CH 3 (U) Two trichloro products.
EXERCISE-III
Q.1 Identify P1 to P8.
H H
CH3 – CH = CH – CH2 CH2 CH3 H
Br
 P1 + P2
D T
H
H Br
CH3 – CH =CH –CH2– CH  CH 2 CH3  P1 + P2 + P3 + P4
|
D T
H Br
CH3 – CH = CH – CH 2  CH  CH 2  CH  CH 3  P1 + P2 + P3 + P4 + P5 + P6 + P7 + P8
| |
D T
Q.2 Give the product of the following reaction.

O
Mg A CH=O Mg

(i) H 2O
(ii) CH=O H 2O B
O O
|| ||
(iii) Me  C  Et Mg
 H
2SO 4
 C (iv) Ph  C  Me Mg
 H
2SO 4
 D
H 2O  H 2O 
Q.3 Identify missing products in the given reaction sequence.

aq KOH
CH3 – CH2 – CH3 Br
2 /
hv
  (A)    (B) H2SO
4  (C) Br
2  (D) = ?
 CCl 4
Q.4 Find out the total no. of products (including stereo) in the given reaction :
CH3
NBS, CCl4 Products.

Peroxide, 
Q.5 With the help of following data show HBr exhibits the peroxide effect.
H10/kJ mol–1 H20/kJ mol–1
   
H–X X + CH2 = CH2  X CH2 – C H2 XCH2– C H2 + H–X  XCH2CH3 + X

HCl –67 + 12.6
HBr –25.1 – 50.2
HI +46 –117.1
Q.6 Addition of small amount of (C2H5)4Pb to a mixture of methane and chlorine, starts the reaction at
140°C instead of the usual minimum 250°C. Why?
Q.7 On chlorination, an equimolar mixture of ethane and neopentane yields neopentyl chloride and
ethyl chloride in the ratio 2.3 : 1. How does the reactivity of 1° hydrogen in neopentane compare with
that of a 1° hydrogen in ethane?
Q.8 It required 0.7 g of a hydrocarbon (A) to react completely with Br2 (2.0 g) and form a non resolvable
product. On treatment of (A) with HBr it yielded monobromo alkane (B). The same compound (B) was
obtained when (A) was treated with HBr in presence of peroxide. Write down the structure formula of
(A) and (B) and explain the reactions involved.
Q.9 Give product(s) in each of the following reactions .
(a) CH3 – CH – CH2 – CH2– CH3 Br / hv

2  (A) (major)
|
CH 3
( C H5COO)2
(b) + NBS 6   (B)
hv
(c) CH3 – CH2 – CH = CH2 + Me3COCl  (C) + (D)
CH 3
|
CH 3 C O Cl / 
|
CH 3
(d) C6H5 – CH2 – CH2 – CH3      (E) (major)
Q.10 We saw that acid-catalyzed dehydration of 2,2-dimethyl-cyclohexanol afforded 1,2-dimethylcyclohexene.

To explain this product we must write a mechanism for the reaction in which a methyl shift transforms a
secondary carbocation to a tertiary one. Another product of the dehydration of 2,2-dimethylcyclohexanol
is isopropylidencyclopentane. Write a mechanism to rationalize its formation.

H
heat
 + C(CH3)2
2,2-Dimethylcyclohexanol 1,2-Dimethylcyclohexene Isopropylidenecyclopentane
Q.11 (a) Write a reasonable and detailed mechanism for the following transformation.
conc
 . + H2O
H 2SO 4
H  / HOH
(b)  
-Terpeniol
Q.12 Assuming that cation stability governs the barrier for protonation in H – X additions, predict which
compound in each of the pairs in parts (a) & (b) will be more rapidly hydrochlorinated in a polar solvent.
(I) (II)
(a) CH2 = CH2 or
(b) or
Q.13 Choose the member of the following pairs of unsaturated hydrocarbons that is more reactive towards
acid-catalysed hydration and predict the regiochemistry of the alcohols formed from thi s compound.
(a) or
(I)
(b) or
(c) or
Q.14 Give product in the following reaction.
(i) NaNO
 2  A (ii) NH2  NaNO2
 B
HCl HCl
NH2
CH2NH2 NH2
(iii) NaNO
 2  C (iv) NaNO
 2  D
HCl HCl
(v) NaNO
 2  E
HCl
OH NH2
Q.15 What are the products of the following reactions ?
(a) PhCH = CHCH3 + HBr A (b) + HI  B
(c) + HBr Peroxide

  C (d) + HCl D
Q.16 Complete following reaction:
HCl
(a) 

Br
(b) 2

CCl 4
CH3
Cl
(c) 2

CS2
Total number of products obtained in this reaction is ?

Q.17 H
 Write the mechanism.

OH
Q.18 Compare rate of reaction towards pinacol pinacolone rearrangement.
CH 3 CH 3 CH 3 Ph CH 3 CH 3
| | | | | |
Ph — C — C — Ph CH 3 — C — C — Ph CH 3 — C — C — CH 3
| | | | | |
OH OH OH OH OH OH
( I) ( I I) ( I I I)
Q.19 Calculate the percentage of products i.e. P1, P2 & P3, if reactivity for chlorination with 1°H, 2°H & 3°H
is 1 : 3.8 : 4.5 respectively.
Cl
Cl
Cl
h
+ Cl2    + +
Monochlorination
(P1) (P2) (P3)
Q.20 Write all the monochlorinated products (including stereo) of isohexane.
EXERCISE-I
Q.1 B Q.2 C Q.3 C Q.4 B Q.5 C Q.6 C Q.7 B
Q.8 D Q.9 D Q.10 A Q.11 B Q.12 C Q.13 C Q.14 B
Q.15 C Q.16 B Q.17 D Q.18 C Q.19 A Q.20 A Q.21 D

Q.22 C Q.23 D Q.24 C Q.25 B Q.26 D Q.27 D Q.28 B
Q.29 B Q.30 C Q.31 A Q.32 B Q.33 C Q.34 D Q.35 A
EXERCISE-II
Q.1 B, D Q.2 B, C, D Q.3 A, B, D Q.4 B, D
Q.5 A, B, C Q.6 A, B Q.7 A, B, C Q.8 A, B, D
Q.9 A, B, D Q.10 (A) S,T (B) P,S,T (C) U, (D) Q, (E) T,U
EXERCISE-III
H H H Br H H
| | | | | |
Q.1 P1 = CH 3  C  (CH 2 ) 2  C  CH 2  C  CH 3 P2 = CH 3  C  (CH 2 ) 2  C  CH 2  C  CH 3
| | | | | |
Br D T H D T
H D H Br D H
| | | | | |
P3 = CH 3  C  (CH 2 ) 2  C  CH 2  C  CH 3 P4 = CH 3  C  (CH 2 ) 2  C  CH 2  C  CH 3
| | | | | |
Br H T H H T
H D T Br D T
| | | | | |
| | | | | |
Br H H H H H
Br H T H H T
| | | | | |
| | | | | |
H D H Br D H
OH
* OH
Q.2 (i) (A) (ii) (B) RR, SS, RS (3 products)
OH * OH
CH3 Ch3
(iii) (C) CH3 – C – C – Et (iv) (D) CH3 – C – C – Ph
|| Et || Ph
O O
Br OH
| |
Br2 / hv aq KOH
Q.3 CH3 – CH2 – CH3   CH 3  CH  CH 3    CH 3  CH  CH 3
( A) (B)
Br2
H2SO4
CH 2  CH  CH 3  CH 2  CH  CH 3
| | CCl 4 (C)
Br Br
(D)
Q.4 9 Q.7 1.15 times more reaction Q.8 A=
Br
|
Q.9 (a) A: CH 3  C  CH 2CH 2CH 3 (b) B:
|
CH 3
(c) C: CH 3  CH  CH  CH 2 D: CH 3  CH  CH  CH 2 Cl
|
Cl
(d) E: Ph  CH  Et
|
Cl
Q.11 (b) H  HOH / H 

  
Q.12 (a) II, (b) I Q.13 (a) II, (b) I, (c) II ;
Q.15 (a) Ph  CH  Et , (b) Me2C(I)–Et, (c) , (d)

|
Br
CH3 Cl
H + H
Q.16 (a) Cl CH3 (diastereoisomers)
CH3 CH3
(b) + (diastereoisomers)
Me Me
H Cl Cl H
(c) H + H (Enantiomers)
Cl Cl
Et Et

 
H –H2O –H
Q.17  H
OH OH2
Q.18 More stable the carbocation, more will be the rate of reaction. II > I > III
Q.19 P1 = 13.26 %, P2 = 66.96 %, P3 = 19.82 % Q.20 8 products
GRIGNARD REAGENT FINAL LAP - 2019
Q.1 The order of reactivity of alkyl halide in the reaction R–X + Mg  RMgX is
(A) RI > RBr > RCl (B) RCl > RBr > RI (C) RBr > RCl > RI (D) RBr > RI> RCl
Q.2 Br–CH2–CC–CH2–Br Mg

 BrMg–CH2–CC–CH2–MgBr
( excess)
Et 2O
Product
The major product is:
(A) Br–Mg–CH2–CC–CH2–Br (B) Cyclobutyne
(C) —(CH 2  C  C  CH 2—
)n (D) CH2 = C=C=CH2
Q.3 On conversion into Grignard followed by treatment with ethanol, how many alkyl halides (excluding
stereoisomers) would yield 2-methyl butane.
(A) 2 (B) 3 (C) 4 (D) 5
Q.4 Which of the following reacts with Grignard reagent to give alkane?
(A) nitro ethane (B) acetyl acetone (C) acetaldehyde (D) acetone
Q.5 How many litres of methane would be produced when 0.595 g of CH3MgBr is treated with excess of
C4H9NH2
(A) 0.8 litre (B) 0.08 litre (C) 0.112 litre (D) 1.12 litre
Q.6 How many litres of ethene would be produced when 2.62 g of vinyl magnesium bromide is treated with
224 ml of ethyne at STP.
(A) 0.224 litre (B) 0.08 litre (C) 0.448 litre (D) 1.12 litre
MgBr OH
Q.7 +  A
O – Ph
(A) (B) (C) (D)
Q.8 In which of the following reactions 3°alcohol will be obtained as a product.

O
||
(A) MgBr (excess) + H  C  Cl  

H
O
||
(B) PhMgBr (excess) + CH 3  C  Cl  

H
O O
|| ||
(C) CH3MgBr (excess) + CH 3  C  O  C  CH 3  

H
O
||
(D) CH3MgBr (excess) + Cl  C  O  Et  

H
Q.9 1
equivalent Mg
  X D2O
  Y; Y is
ether
(A) (B) (C) (D) None of these
Q.10 Compounds are shown with the no. of RMgX required for complete reaction, select the incorrect option
(A) CH3COOC2 H5 1
(B) CH3COCl 2
(C) HOCH2COOC2H5 3
(D) 4
Q.11 What will be the order of reactivity of the following carbonyl compounds with Grignard's reagent?
H H CH3 Me3C
(I) C=O (II) C=O (III) C=O (IV) C=O
H CH3 CH3 Me3C
(A) I > II > III > IV (B) IV > III > II > I
(C) II > I > IV > III (D) III > II > I > IV
OH
Q.12 Carbonyl compound (X) + Grignard reagent (Y) Me Ph
Et
X , Y will be
O O
|| ||
(A) Et  C  Ph , Me Mg Br (B) Me  C  Ph , Et Mg Br
O O
|| ||
(C) Me  C  Et , Ph Mg Br (D) Et  C  Ph , Et Mg Br
Q.13 (R) - 2-Bromooctane (

i ) Mg
 X
(ii ) CO 2
(iii ) H 
X is
(A) (B)
(C) A and B both (D) None of these
Q.14 In which one of the following reaction products are not correctly matched in
(A) RMgX + CO2   
Carboxylic acid
(2) H
(B) RMgX + C2H5OH  Alkane

(C) RMgX + CH3CH2Cl  Alkene
(D) RMgX + Cl O  Ether
Q.15 The number of moles of grignard reagent consumed per mole of the compound
is:
(A) 4 (B) 2 (C) 3 (D) 1
Q.16 Select the correct statement:

(A) 1,4-dibromobutane react with excess of magnesium in ether to generate di-Grignard reagent.
(B) 1,2-dichlorocyclohexane treated with excess of Mg in ether produces cyclohexene.
(C) Vicinal dihalides undergo dehalogenation to give alkene when heated with Zn dust or Mg.
(D) 1,3-dichloropropane by treatment with Zn dust or Mg forms cyclopropane.
O
||
CH3  C CH3 
Q.17 CH3–CH=CH2 Br
2       H
Mg
Dry ether
 NH4 Cl 
End product of above reaction is
CH 2
||
(A) CH 2  CH  CH 2  C  CH 3 (B) H 2C  CH  CH  C  CH 3
|
OH CH 3
|
(C) H 2C  CH  CH 2  C  CH 3 (D) H 2C  CH  CH 2  CH  CH 2  OH
| |
CH 3 CH 3
O
Q.18 MgBr + H–C–Cl  product.
O
||
(A) C  CH 3 (B) CH2CH=O
(C) CH = O (D) CH  CH 3
|
CH  O
Br
Q.19  1
. Mg / ether
    Product (s)

2. CH 3CHCH2 CH 3. H 3O
| ||
OH O
Select the product from the following
I: II : CH 3CHCH 2CH III :

| ||
OH O
(A) III (B) I, III (C) I, II (D) II, III
O
||
Q.20 C 2 H 5 O  C  OC 2 H 5 2
CH 3MgBr
  A. Product A formed
(A) is ethyl acetate
(B) further react with CH3MgBr/H2O+ to give acetone
(C) further react with CH3MgBr/H2O+ to give t-butyl alcohol
(D) Can give pinacol when treated with Mg followed by H2O
Q.21 Order of rate of reaction of following compound with phenyl magnesium bromide is:
O O O
|| || ||
Me  C  Cl Me  C  H Me  C  O  Et
I II III
(A) I > II > III (B) II > III > I (C) III > I > II (D) II > I > III
Q.22 Select the correct order of decreasing reactivity of the following compounds towards the attack of
Grignard reagent
(I) Methyl benzoate (II) Benzaldehyde (III) Benzoylchloride (IV) Acetophenone
(A) II > III > I > IV (B) III > IV > II > I
(C) III > II > IV > I (D) II > IV > I > III
CH3MgX
Q.23 O NH4Cl Product is
(A) Enantiomer (B) Diastereisomer (C) Meso (D) Achiral
Q.24 Nucleophilic addition of Grignard reagent cannot occur in
O O O O
|| || || ||
(A) CH 3  C  C  CH 3 (B) CH 3  C  CH 2  C  CH 3
O O
|| || O
(C) CH 3  C  CH 2  CH 2  C  CH 3 (D)
O
CH MgBr
Q.25 CH 3CCH 2CH 2CH 2Cl 3 A, A is

||
O
CH 3
|
(A) CH 3 CCH 2 CH 2 CH 2 Cl (B) CH 3CCH 2CH 2CH 2CH 3
|
OH ||
O
(C) (D)
O O
|| ||
Q.26 CH 3CCH 2 CH 2 COCH 2 CH 3 (
i ) CH 3MgBr ( one mol )
     A, A formed in this reaction is
( ii ) H 3O 
OH O O O
| || || ||
(A) CH 3CCH 2CH 2COCH 2CH 3 (B) CH 3CCH 2CH 2CCH 3
|
CH 3
CH 3 CH 3
| |
(C) (D) CH 3CCH 2CH 2CCH 3
| |
OH OH
Cl2 Mg 3 CH CHO
Q.27 PhCH3  (A)  (B)    (C)
h ether NH4 Cl
CH3
OH
| OH CH3 OH
CH2 – CH – CH3 CH3 |
CH – CH3 C – CH3
(A) (B) (C) (D)
CH CH3
HO CH3
Q.28 Select the correct order of reactivity towards Grignard reagent for nucleophilic attack.
O O
|| ||
(A) R  C  R > R  C  H
(B) Cl  CH 2  C  H > CH 3CH 2  C  H
|| ||
O O
O O
|| ||
(C) CH 3  C  O NO2 < CH 3  C  O
O O
|| ||
(D) R  C  OR > R  C  NR 2
Q.29 In the reaction sequence:
( i ) CH MgBr / CuCl
 3    (X) Major + (Y)
( ii ) H 2O / H 
(X) & (Y) respectively are

OH CH3 OH
(A) , (B) ,
CH3
(C) , (D) ,
(2)
O OH
C
Q.30 O (3)
RMgX
( 2 moles)
 
H
H
(1)
S
C

CH
(4)
Deprotonation will occur from the following positions:

(A) 1,2 (B) 1,3 (C) any two positions (D) 1,4
Q.31 Which of the following reacts with 4 moles of RMgX.
COCl CH2–Cl
ROC
(A) (B)
CHO COOEt
OH
CH=CH2
EtO CHO
O
O
(C) O (D) RN
H O
Et
Br
14
NaHCO
Q.32 Mg
 (A) (
i ) CO 2
 (B)  3  (C) gas
( ii ) H  / H 2O
Product C is
(A) CO (B) 14CO
2
(C) CO2 (D) A mixture of 14CO2 and CO2
3 ( i ) CH ONH
Q.33 2CH3 MgBr ( 2 
ii ) H 
(A) CH3 –O–NH–CH3 (B) CH3–NH–CH3

(C) CH3 –NH2 (D) CH3 –OH
O OH
Q.34 (
i ) CH 3MgBr
  (A)
( ii ) H  / H 2 O
CH3
(A) The product is optically active
(B) The product contains plane of symmetry
(C) The product shows geometrical isomerism.
(D) The product shows optical isomerism.
Q.35 Which of the following is incorrect.

O
O
C ||
CH3MgX
(A) Cl OC2H5     CH 3  C  OC2 H 5
(1 eq )
O
OC2H5 ||
C 2 H5MgX
(B) CH3–C OC2H5    CH 3  C  OC2 H 5
(1eq )
OC2H5
S S
||  ||
(C) CH3MgX + C = S H
3O
 CH 3  C  SH
O O
||  ||
(D) CH3MgX + C = O H
3O
 CH3  C  OH
Q.36 Which of the following reacts faster with RMgX.
O O O O
|| || || ||
(A) R  C  Br (B) R  C  H (C) R  C  OEt (D) R  C  NH 2
O
||

Q.37 CH3MgBr + CH2=CH  C  H H Product (1, 4 addition). It is
3O
OH
|
(A) CH 2  CH  C  H (B) CH 2CH  CH  CH 3
| |
CH 3 OH
(C) CH3CH2CH2CHO (D) none
Q.38 (
i ) PhMgBr
  Product.
(ii ) NH 4Cl
Me
Products in this reaction will be
(A) Stereoisomers (B) Enantiomer (C) Diastereomers (D) Geometrical isomers
CH MgBr (1 eq .)
Q.39 3   ?
The product is:
(A) (B) (C) (D)
Q.40 CH2 = C = O (

i ) Br2
 C4H8O
(ii ) CH 3MgBr
( 2 equi )
(A) (B) (C) (D) All of these
( i ) CH CN
Q.41 RMgX  3   (A) ( i ) RMgX
 (B) will be
( ii ) H 3O  ( ii ) aq. NH 4Cl
(A) 1° ROH (B) 2° ROH (C) 3° ROH (D) Alkene
Q.42 CH3—CH—CH2 CH

3MgCl

H 2O
O
(A) CH 3  CH  CH 2OH (B) CH 3  CH  CH 2  CH 3
| |
CH 3 OH
(C) CH 3  CH  CH 3 (D) HO – CH2 – CH2 – CH2 – CH2 – OH
|
CH 3
Q.43 The reaction of 1 mole each of p-hydroxy acetophenone and methyl magnesium iodide will give
O O
(A) CH4 + IMgO C—CH3 (B) CH3–O C—CH3
OMgI MgI
O
(C) CH3–C OH (D) CH3O C—CH3
CH3
r1
Q.44 (i) + Ph Mg Br 
 Ph CH2 CH2 OH
O
r2
(ii) + Ph Mg Br  Ph CH2 CH2 CH2 OH
O
(A) r2 > r1 (B) r1 > r2 (C) r1 = r2 (D) r1 = 2r2
Q.45 How many moles of Grignard reagent will be required by one mole of given compound?
O
SH
HO C – OEt
C – Cl
CH2–CH2 O
Cl
(A) 7 (B) 6 (C) 8 (D) 5
Q.46 Consider the given organometallic compound.

(I) (CH3)2Hg (II) (CH3)2Zn (III) (CH3)2Mg (IV) CH3Li
The correct decreasing order of ionic character is
(A) I > II > III > IV (B) II > I > III > IV (C) I > III > II > IV (D) IV > III > II > I
O (i) CH3MgBr
|| + P
(ii) H3O
Q.47 CH3CH = CH  C  CH 3
(i) CuI,CH3MgBr
+ Q
(ii) H3O
OH OH
| |
(A) P is CH3CH = CH  C  Me Q is CH3CH = CH  C  Me
| |
Me Me
O OH
|| |
(B) P is CH 3CH  CH 2  C  CH 3 Q is CH3CH = CH  C  Me
| |
CH 3 Me
(C) P is CH 3CH  CH  C(CH 3 ) 2 Q is (CH 3 ) 2 CHCH 2C  CH 3

| ||
OH O
(D) P is (CH 3 ) 2 CHCH 2C  CH 3 Q is CH 3CH  CH  C(CH 3 ) 2

|| |
O OH
For Q. No.48 to Q. No. 50
Consider the given reaction and answer the following questions
COOCH3
MeMgBr
  Products
O OCH3 (excess)
O SH
||
O
Q.48 No. of RMgX consumed in the reaction is

(A) 4 (B) 5 (C) 6 (D) 7
Q.49 How many product will be fromed in given reaction (excluding stereo)
(A) 2 (B) 3 (C) 4 (D) 5
Q.50 Which of the following reaction will give the same Hydrocarbon formed as one of the product in the
above reaction.
(A) EtMgBr + Me – OH  (B) PhMgBr + Me – OH 
(C) MeMgBr + Ph – OH  (D) MeMgBr + CH3 – CHO 
Q.51 Compare the two methods shown for the preparation of carboxylic acids:
Mg (i ) CO 2
Method 1: RBr   RMgBr    RCO2H
diethyl ether (ii ) H3O 
H O , HCl
Method 2 : RBr NaCN 2
 RCN   RCO2H
heat
Which of the following statements correctly describes this conversion?

(A) Both method 1 and method 2 are appropriate for carrying out this conversion.
(B) Neither method 1 nor method 2 is appropriate for carrying out this conversion.
(C) Method 1 will work well, but method 2 is not appropriate.
(D) Method 2 will work well, but method 1 is not appropriate.
Q.52 Which of the given compound can not show acid-base reaction with Grignard reagent.
(A) CH3–NO2 (B) (C) Cl (D)
Cl O
C
Cl O O
Q.53 (a) O RMgCl

 Number of moles of Grignard reagent consumed.
Cl ( excess )
OMe SH
(b) Number of mole of Grignard consumed in given molecule.(When Grignard reagent is in excess)
ONH2
O
O
O NHCl
Q.1 A Q.2 D Q.3 C Q.4 A,B Q.5 C
Q.6 C Q.7 A Q.8 B,C,D Q.9 D Q.10 A
Q.11 A Q.12 A,B,C Q.13 C Q.14 C Q.15 A
Q.16 A,C,D Q.17 B Q.18 C Q.19 C Q.20 C,D
Q.21 A Q.22 C Q.23 A Q.24 B,D Q.25 C
Q.26 C Q.27 A,B,C Q.28 B,D Q.29 B Q.30 A
Q.31 D Q.32 C Q.33 C,D Q.34 B,C Q.35 B
Q.36 D Q.37 C Q.38 A,C,D Q.39 D Q.40 A
Q.41 C Q.42 B Q.43 A Q.44 B Q.45 A
Q.46 D Q.47 C Q.48 C Q.49 C Q.50 C
Q.51 C Q.52 D Q.53 (a)-7, (b)-7
OXIDATION & REDUCTION FINAL LAP - 2019
OXIDATION OF ALKENES, ALCOHOLS & CARBONYL COMPOUNDS
(I) OXIDATION OF ALKENES

OsO4
R–CH=CR2 R–CH—CR2
H2O
OH OH
Cold dil. R–CH—CR2
alkaline
KMnO4 OH OH
* Cold dil. alkaline KMnO4 is called as Bayer’s reagent.
* Overall syn addition
* Given by alkenes & alkynes
* Benzene & Cyclopropane can not give this reaction.
If we use acidic KMnO4 or warm KMnO4 or too concentrated KMnO4 the oxidative cleavage of
Glycol occurs resulting in mixture of Carboxylic acids & Ketones.

H ,KMnO 4
R–CH = CR2     RCOOH + R2C = O

Hot acidic KMnO4, Hot acidic K2Cr2O7 & hot acidic NaIO4 gives same result with alkene. The effect
is similar to that of oxidative ozonolysis on alkenes.
Preilschaive reaction :
Epoxidation of alkenes is reaction of alkenes with peroxyacids.
O O
|| ||
CH2=CH2 + CH 3  C  O  O  H  CH2–CH2 + CH 3  C  OH
O
 With the decrease in nucleophilicity of double bond, rate of reaction decreases.
 With the decrease in ewithdrawing substituents in leaving group, rate decreases.
+
R H R
R R
CH dil.H2SO4 CH + + –H+ HO–CH
O O–H H2O–CH
CH2 CH2
CH2–OH CH2–OH
H2O
RCO3H
O
RCO3H OH R R
H 3O CH + 1 O Ag
OH CH
2 2  O
HCO3H OH CH2 CH2
OH
(II) OXIDATION OF ALCOHOLS
Oxidising agents

(1) Cu / 300°C (or Red hot Cu tube) (2) H /KMnO4,  (Strong oxidising agent)
(3) H/K2Cr2O7,  (Strong oxidising agent) (4) PCC (Pyridinium chloro chromate)

N CrO3 Cl or N
CrO3 + HCl
H
(5) Collin’s reagent (6) Sarett reagent (i.e. PCC in CH2Cl2)
( (2 mol) + CrO3 + CH2Cl2) + CrO3 + HCl + CH2Cl2

N N
(7) PDC (8) Jones reagent (H2CrO4 in Anhydrous acetone)

( Pyridinium dichromate )
Cr2O7
N or CrO3 + H2SO4 in acetone.
 2 Sufficiently mild so that it oxidises alcohols
without oxidising or rearranging double bonds
(8 or 9)
(9) TsCl + DMSO + NaHCO3 (10) MnO2-Oxidises only allylic or benzylic–OH.i.e.
TsCl
RCH2OH s DMSO
 RCH2OTs
  RCHO 1° Allylic or benzylic OH MnO
2  Aldehyde
NaHCO3
TsCl
R2CHOH s DMSO
 R2CH–OTs
  R2CO 2° Allylic or benzylic OH MnO
2  Ketone
NaHCO3
Ts
R3COH Cl  DMSO
s 
 R3C–OTs
NaHCO3
× No effect on 3° ROH and on Carbon-carbon
multiple bond.
(11) Periodic cleavage (12) NBS
A similar oxidation is obtained incase of HIO4
known as periodic cleavage. (13) Openaur oxidation
O
R – CH – R Al(OCMe3)3 R–C–R
O O O
OH CH3 –C – CH3
R–CH–OH HO–I=O R–CH
+ + 
R2C–OH R2C=O R2CH–OH + Al(OCMe3)3Me3COH + Al(OCHR2)3
O
+
O HIO3 (R2CH–O)2 Al–O
O CR2
R– CH — O – I = O H
3Me2C
R2C–O–H O
3R2C=O + (Me2C–O)3 Al
But reaction is only observed for Vic-diols. Oxidation of alcohol with aluminium tertiary
butoxide is Openaur oxidation.
OH O
Al (OCMe3)3
acetone
Different oxidising agents are used to oxidise alcohols in corresponding carbonyl compounds and carboxylic
acids.
mild oxidising
e.g. (I) R  CH 2  OH   R  C  H (Aldehyde) eg. 1,4,5,6,7,8,9,12
1alcohol
agent ||
O
OH O
| mild oxidising
||
(II) R  CH  R '    R  C  R ' (Ketone) eg.1,2,3,4,5,6,7,8,9,12,13
agent
2alcohol
strong oxidising
(III) R  CH 2  OH    R  C  OH eg. 2,3
agent ||
1alcohol
O
CH 3 CH2
| Cu 300C
(IV) CH 3  C  OH   C Dehydration takes place.
| CH3 CH3
CH 3
(V) Double bond or Tripple bond is not affected by 1,4,5,6,7,8,9,10
(VI) No effect on 3° alcohol by 2,3,4,5,6,7,8,9,10,12,13
(III) OXIDATION OF CARBONYL COMPOUNDS.

1. RCHO + [Ag(NH3)2]OH   RCOOH + NH3 + Ag 

Aldehyde acts as reducing agent, they can reduce mild oxidizing agents like Tollen’s Reagent. Tollen’s
test Gentle Heating for 20 to 25 mins.
COONa
2. Fehling’s Solutions
H OH
Fehling’s A Fehling’s B
aq. CuSO4 Alk. solution of Roschelle H OH
salt (sodium potassium tartrate) COOK
It act’s a carrier for Cu2+ as it make reversible complex with Cu2+
This test is also used is Blood and Urine test.
H 2O
RCHO + Cu2+  RCOOH  Cu 
  
RCOO – Cu 2O ( red ppt.)
3. Benedict’s solution
Sodium Citrate + NaOH + NaHCO3 + CuSO4
H 2O
RCHO + Cu2+  RCOOH  Cu 
  
RCOO – Cu 2O ( red ppt.)
4. RCHO + HgCl2 + H2O  RCOOH + 2HCl + Hg2Cl2


RCHO + Hg2Cl2 + H2O  RCOOH + 2HCl + 2Hg  greyish solution
5. Schiff’s Reagent
Schiff’s Reagent is aq. solution of following base decolourised by passing SO2.
Aldehyde restore pink colour of Schiff’s reagent.
NH2 NH2
SO 2 Colourless RCHO
C RCOOH + Pink colour
solution 
(Schiff’s Reagent)
+ NH
2Cl
p-Rosaniline Hydrochloride
Magenta colour (Fuschin)
Ketons are not easy to oxidize so they do not give these 5 tests. These five tests can be used to distinguish
aldehyde and ketones. Both gives 2,4 DNP test
KETONES ARE DIFFICULT TO OXIDIZE

Ketones can be oxidized from their enolic form at high temperature with very strong oxidizing agent.
Oxidation of ketones is sometimes governed by Popoff’s rule. According to this rule carbonyl group
remains with the smaller alkyl group. More electron rich alkene will be easy to oxidized.
O
[O]
Me – C – Me MeCOOH + CO2 + H2O

Allylic oxidation
SeO2 is a selective oxidizing agent with converts –CH2– group adjacent to carbonyl group into carbonyl
group.The reagent, in general, oxidises active methylene and methyl groups to ketonic and aldehydic
groups respectively.
O O O O O
|| SeO2
|| || || SeO2
||
 CH 2  C    C  C  ;  C  CH 3    C  CHO
Double bonds, triple bonds and aromatic rings may also activate the methylene group.The methylene or
methyl group  to the most highly substitued end of the double bond is hydroxylated according to the
order of preference of oxidation CH2 > CH3 > CH groups.
OH
|
SeO 2
CH3= CH–CH3  CH 2  CH  CH 2
2° C – H > 1° C – H > 3° C – H
Rate of reactivity order
CH3 – CH = CH – CH2–CH3 SeO
2  CH 3  CH  CH  CH 2  CH 3
|
OH
CH3 HO–CH2
SeO2
CH – CH3 CH – CH3
CH3 CH3
HO
SeO2

H / KMnO H  / KMnO
CH2 = CH2  CH3–CH= CH2 
4 4
Q.1 (i) (ii)
 
 
H / KMnO4 H / KMnO4
(iii)  (iv) 
 
 
H / KMnO4 H / KMnO4
(v)  (vi) 
 
 
H / KMnO4 H / KMnO4
(vii)  (viii) 
 
 
H / KMnO4 H / KMnO4
(ix)  (x) 
 

H / KMnO4
(xi) 

H  / KMnO
C10H10 
4
(xii) HOOC  C  C  C  COOH
 |
C  COOH
Q.2 A to F alkenes with minimum possible carbon.

H  / KMnO
A 
4
(i) MeCOOH as the only product

H  / KMnO
B 
4
(ii) O as the only organic product

H  / KMnO
C 
4
(iii) MeCH2COOH as the only organic product

H  / KMnO
D 
4
(iv)

O
O
H / KMnO4  ||
(v) E  HOOC  C  C  C  C  C  C  C  C  COOH
 ||
O
H  / KMnO
F 
4
(vi) acetone + ethanoic acid

1% alkaline mCPBA
Q.3 (i) (A) (ii)
KMnO4
mCPBA\hydrolysis
(B)
Me Me
mCPBA mCPBA
(iii) hydrolysis (iv) C=C hydrolysis
Me H H
Me Me 1
H H Ag2O or 2Ag + O
mCPBA 2 2
(v) C=C (vi) C=C 
H Me hydrolysis H Ph
KMnO / OH ¯,
Q.4 (i) CH3– CH2 – CH2 – OH  4   ?

or KMnO 4 / H ,

K2Cr2O7 / H , 
?
or conc. HNO 3, 
OH
| KMnO ,H 
(ii) CH 3  CH  CH 2  CH 3  4  ?

or K 2Cr2O 7 , H
OH
HO (1)
?
(2) or (3)
?
(4) or (5) or (6)
(iii) OH ?
or (7) or (8) or (9)
HO
(10)
?
Q.5 (i) CH2 = CH – (CH2)3 – CH2 – OH PCC


(ii) C6H5 – CH = CH – CH2 –OH PCC


OH
| (i ) Dil NaOH
(iii) CH 3  CH  CH 2  CH 2  CH 2  OH PCC
 (A)    (B)
( ii ) 
OH
(iv) PCC
 (v) CH2 = CH – CH2–OH MnO
2  ?
CH2OH
OH
MnO
(vi) CH3O CH–CH2 –CH2 –OH 2  ?
Acetone
CH3O
CH 3 OH
| MnO 2 |
(vii) CH  C  CH  C  CH 2  OH Acetone
 ? (viii) C 6 H 5  CH  CH 3 MnO
2  ?
CCl 4
(ix) C 6 H 5  CH  CH  CH 2  CH  CH 2  OH DMSO
 TsCl  NaHCO3
  ?
|
CH 3
Q.6 (i) HO Aluminium

  tert butoxide
  ?
Acetone
OH
|
(ii) CH 2  CH  CH 2  CH  CH 3 Aluminium

OH
(iii) Aluminium
  ?
p  benzoquinone
Q.7 Which one of the following alcohols are oxidised by MnO2?

OH
|
(A) C6H5 – CH2 – CH2–OH (B) CH 2  CH  CH 2  CH  CH 3
OH
|
(C) CH 3  CH  CH  CH  CH 3 (D) CH3–CH2 – CH2 –OH
Q.8
HIO HIO
(i) Me  CH  CH 2  OH 4  (ii) Me 2 C — CH — Et 4 
 
| | |
OH OH OH
OH
(iv) HO  CH 2  CH 2  CH
(iii) HIO
4   CH 2  OH HIO 4
 | 
OH 
OH
(v) CH 2 — CH  CH 2  CH 3 HIO
4  (vi) CH 2 — CH  CH  CH 3 HIO 4 
 | | | 
| |
OH OH OH OH OH
(vii) CH 2 — CH  CH  CH 2 HIO
4  (viii) Me  C  CH  Me HIO
4 
| | | |  || | 
OH OH OH OH O OH
(ix) Me  C  C  Me HIO
4 
| | || 
O O
Q.9 Which will give the Tollen test.
O OH O OMe O OH HO
|| |
(i) H (ii) (iii) R  C  CH 2 (iv)
HO
O O
[O] [O]
Q.10 (a) C – C – C –C (b) Me2CH–C–Me
 
O
O [O]
[O]
(c) Me3C–C–Me (d)
 
SeO2 SeO2
Q.11 (a) CH3–CHO (b) Me2CO
 
O
SeO2
(c) C – C – C –C CP1– C–mCPBA
C–C P2 LAH
 P3

O SeO
2
(d) (e) SeO2

O
CH3 C H
? Acrolein 2 step
(f) CH3 – CH = CH2 (g)
(1) step etard
O O O +
SeO2 conc. NaOH H /
(h) CH3 –C – H H–C–C–H P1 P2
Q.12 How will you differentiate HCHO and PhCHO ?
Q.13 How will you differentiate HCHO and MeCHO ?
Reducing agents and their role
Group Product LAH in LiAlH(OCMe3)3 NaBH4 LiAH4 B2H6 H2+

ether in THF in EtOH +AlCl3 in THF catalyst
–CHO –CH2OH + – + + + +
>C=O >CH–OH + – + + + +
–CO2H –CH2OH + – – + + +
–CO2R –CH2OH + – – + + +
–COCl –CH2OH + +* + + – +
–CONH2 –CH2NH2 + – – + + +
(RCO)2O RCH2OH + – – + + +
–CN –CH2NH2 + – – + + +
>C=NOH –CH2NH 2 + – – + – +
>C=C< >CH–CH< – – – – + +
–CC– –CH=CH– – – – + + +
1° RX RH + – – + – +
* Product is RCHO
Q.1 How many alkene on catalytic reduction give corresponding products.
(i) (A) H 2 / Pt
 n-butane (ii) (B) H 2 / Pt
 Iso-pentane
(iii) (C) H
2 / Pt
 Neo-pentane (iv) (D) H
2 / Pt
 Cyclopentane
H2
(v) (E) 
Pt
Q.2 Give the expected major product for each reaction, including stereochemistry where applicable.
H2 D2
(a) CH3–CH2–CH=CH2 
Pt
P1 (b) Pt P2
H3C H Me
C=C D2
 P
(c) Ni 3 (d) Ni
/ H2  P4
H CH3 Me
H 2/Pt
excess P5
(e) H 2/Pt
1 eq. P6
H 2/Pt H 2/Pt
excess P1 excess P3
Q.3 (i) CH2 = CH–CH2 – CH = O H 2/Pt (ii) CH2=CH–CH2–CN H 2/Pt
1 eq. P2 1 eq. P4
Q.4 Identify the product?
NaBH4 LiAlH4
(i)    Me–CHO LiAlH
 4  (ii) NaBH4
   Me2CO   
NaBH4
(iii)    Me–COCl LiAlH
 4  (iv) NaBH4

LiAlH4
  Me–COOEt   
NaBH4 LiAlH4 NaBH4
(v)    Me–COOH    (vi)    Me–COOMe LiAlH
 4 
NaBH4 LiAlH4
(vii)    Me–CONH2 LiAlH
 4  (viii) NaBH4
   Me–CONH–Me   
NaBH4 NaBH4 LiAlH4
(ix)    Me–CONMe2 LiAlH
4  (x)    Me–CH=NH   
NaBH4
(xi)    CH3–CH = CH2 LiAlH
 4 
Q.5 Give product in following reactions.
NaBH4 LiAlH4 NaBH4 LiAlH4
(i)   O    (ii)    H–N O   
LiAlH4
(iii) NaBH4
  O    (iv) NaBH4
  LiAlH
 4 
N N
H
(v) NaBH4
  O LiAlH
 4  (vi) NaBH4
 
LiAlH4
O   
O O
O
(vii) NaBH4
   Me–CO–N LiAlH
 4  (viii) NaBH4

LiAlH4
  CH2=CH–CHO   
LiAlH4
(ix) NaBH4
   Ph–CH=CH–CHO    (x) NaBH4
  LiAlH
 4 
O
O
O
(a) H Re
dP  HI
 (b) Re
dP  HI

OH
CHO
COCH3
(c) Re
dP  HI

HO CH 2OH
(i) LAH
 (ii)
N O
H3CCOO COOCH3
LAH
(iii) CH3– CH – CH2 (iv) LiAlH
 4  (A) + (B) + (C)
O
LAH
AlCl3
O
(v)
O

CHO
O
LAH
(i) NaBH4 (ii) C—OEt (A)NaOI
 (B)
O
COOEt
(iii) LiAlH 4, D 2O
LiAlH4
H2O
Q.9
(a) O=C—CH3    (A) NBS

Zn ( Hg )
 (B) alc
 .
(C) HCl
 (D)
HCl KOH R 2O 2
O O
Zn ( Hg ) || Zn ( Hg )
(b)  
 (c) Ph  C  CH 3  

HCl ,  HCl
O O
(d) Zn
( Hg
) 
 (e) (
i ) H 2 NNH 2
 
HCl , H 2 O
(ii ) KOH ,heat
N2H4
KOH, heat
O O (excess)
(f) Zn(Hg)
O HCl
(excess)
Q.10 Suggest appropriate reagents for following conversion.

O OH
O
(i) ?
 O
C—H
C—H
O OH
O C—OEt ? O C—H
(ii) 

H
OH
A
O O
(iii) B
OH
C
OXIDATION
Q.1 (i) CO 2 (ii) CH3–COOH + CO2
(iii) O + CO2 + HOOC – C – C – C–COOH (iv) O + CH3–COOH
COOH
(v) (vi) O
COOH COOH
O
(vii) (viii) 2CH3–COOH + CO2
O
COOH CH 2  COOH O CH 2  COOH

(ix) | + | (x) + |
COOH CH 2  COOH O CH 2  COOH
O COOH
(xi)
HOOC O
(xii) CH  C  CH 2  CH  CH 2  C  CH
|
CH 2
|
C  CH
Q.2 (i) Me–CH=CH–CH3 (ii)
(iii) Me–CH2–CH=CH–CH2–CH3 (iv)
(v) (vi)
OH
Q.3 (i) (A) OH (ii) O
(B)
OH
OH
OH Me Me
OH H OH HO H
(iii) (iv) HO H H OH
Me Me
OH OH Me Me
Me
H OH Me H
(v) H OH (vi) C—C
Me H O Ph
Q.4 (i) CH3–CH2–COO , CH3–CH2–COOH

O
||
(ii) CH 3  C  CH 2  CH 3
O O OH O OH

(iii) (1) (2) or (3) O O
O O
O O
CHO O COOH
O OH
(4) or (5) or (6) or (7) or (8) or (9)

O
CHO
OH
HO
(10)
O
HO
Q.5 (i) CH2 = CH – (CH2)3 – CHO (ii) Ph – CH = CH – CHO

O
O
||
(iii) (A) H 3C  C  CH 2  CH 2  CHO (B)
(iv) (v) H2C = CH–CHO

CHO
O
CH 3
MeO C–CH2–CH2–OH |
(vi) (vii) CH  C  CH  C  CHO
MeO
O
||
(viii) Ph  C  CH 3 (ix) Ph  CH  CH  CH 2  CH  CHO
|
CH 3
O O
|| CHO
Q.6 (i) (ii) CH 2  CH  CH 2  C  CH 3 (iii)
Q.7 C
Q.8 (i) Me–CHO + HCHO (ii) O + Et – CHO
CHO
(iii) (iv) HO–CH2–CH2–CHO + HCHO
CHO
(v) HCHO + CH3– CH2–CHO (vi) HCHO + HCOOH + CH3–CHO
(vii) 2HCHO + 2HCOOH (viii) Me–COOH + Me–CHO
(ix) 2 Me–COOH
Q.9 (i), (iii), (iv)

O O O
[O] Me CH–C–Me(c) Me3C–COOH + CO2 + H2O
Q.10 (a) Me CH–C–Me(b)
2C–COOH Me2CO + MeCOOH
COOH
(d) COOH
SeO SeO
Q.11 (a)
CH –CHO CH – CHO (b) Me – C – C – H
O O O
O O O O O
SeO2 | | || | | ||
(c) C – C – C –C mCPBA
CC–CC–CC–CC  C  C  O  C  C LAH
 CH3–CH2–OH

O SeO O HO
(d) (e)
O
O
CH3 C H
? Acrolein 2 step
(f) CH3 – CH = CH2 (g)
(1) step etard
SeO2
MnO2 SeO2
CH2 – CH = CH2 H – C – CH = CH2
CH2 OH MnO2
OH O
O O O +
SeO2 conc. NaOH H /
(h) CH3 –C – H H–C–C–H HCOONa HCOOH
+ CH3OH + CH3OH
Q.12 F and B test Q.13 Iodoform test
REDUCTION
CCC  C CC  CC CCCC
Q.1 (i) cis & trans 2-butene & 1-butene; (ii) | ||
|
C C C
(iii) zero (Neo-pentane can not be prepared by catalytic hyrogenation of alkene); (iv) One
(v) Including optical = 4 , Excluding optical = 3
Q.2 (a) (b)

D
CH3 CH3
CH3
H D D H
H
(c) D H H D (d) CH3
CH3 CH3 H
(e) *
2 G.I.
Q.3 (i) P1 CH3–CH2–CH2–CH2–OH
P2 CH2=CH–CH2–CH2–OH
(ii) P3 CH3–CH2–CH2–CH2–NH2
P4 CH2=CH–CH2–CH = NH
Q.4 (i) MeCH2–OH, Me–CH2OH (ii) Me2CH–OH, Me2CH–OH
(iii) MeCH2–OH, Me–CH2OH (iv) No reaction , Me–CH2–OH + EtOH
(v) No reduction, MeCH2–OH (vi) No reaction, MeCH2–OH + MeOH
(vii) No reduction, MeCH2NH2 (viii) No reaction, Me–CH2–NH–Me

Me
(ix) No reduction, MeCH2–N (x) No reaction, Me–CH2–NH2
Me
(xi) No reaction, No reaction
Q.5 (i) OH , OH (ii) NH OH , NH OH
(iii) No reaction, (iv) No reaction,

NH NH
(v) No reaction, CH2OH (vi) No reaction, CH2OH

OH OH
(vii) No reaction, Me–CH2–N (viii) CH 2=CH–CH2–OH, CH2=CH–CH2–OH
(ix) Ph–CH=CH–CH2–OH, Ph–CH2–CH2–CH2–OH
(x) ,
HO HO
Q.6 (a) (b) (c)

CH3
OH CH OH
2
Q.7 (i) (ii)
N
(iii) CH3– CH – CH3 , CH3–CH2–CH2OH

OH
HO CH2OH OH
NaOI
(iv) + MeOH (B) + Et–OH (C)   By only (C)
test
(v)
CH2OH
(A)
Q.8
CHO CH2OH
CH2OH
(i) NaBH4 OH + EtOH
OH O
COOEt CH CH2OH
CH COOEt
CH3
CH3
(ii) CH2OH + EtOHNaOI

 +Iodoform test
OD OH
(iii) H
Q.9
(a)
O
H
C—CH3 CH2—CH3 CH=CH2 Cl—CH–CH3
Br—C—CH3
Zn
( Hg
) 
 NBS
 alc
.KOH

 HCl

HCl R 2O 2
(b) (c) Ph–CH2–CH3 (d) (e)
O O
(f) ,
R R O
HO—CH2
Q.10 (i) Protection Glycol C=O +  C cyclic-acetal
H HO—CH2 H O
Glycol is used for protection of aldehyde and Ketone.
O
O
CH2–OH OH
O CH2–OH
C—H H
 O LiAlH
 4  O
CH H 3O 
O C—H
(iii) (A) Ni will reduce alkene, aldehyde and all it is not specific ;(B) NH2 – NH2 / H2O2 ;(C) LiAlH4
NAME REACTIONS FINAL LAP - 2019
(1) ALDOL CONDENSATION

The -hydrogen of carbonyl compounds are acidic due to the fact that the anion (enolate ion) is stabilized
by resonance.

H
| OH (base) 
CH2 – C – H CH2 = C – H CH2 – C – H
|| | ||
O O O
(3 Hydrogens) (enolate anion) (enolate anion)
Base catalysed Aldol

In aqueous base, two acetaldehyde molecules react to form a -hydroxy aldehyde called aldol. The
reaction is called Aldol condensation. The enolate ion is the intermediate in the aldol condensation of
aldehyde and ketone. Acetaldehyde for instance, forms a dimeric product aldol in presence of a dilute
base (10% NaOH).

O H / HOH 
2CH3CHO    CH 3  CH  CH 2  CHO  CH3 – CH = CH – CHO
5 C |  H 2O
OH
-hydroxy butyraldehyde (Aldol)
Mechanism :
 O
OH
H H–C–CH3 O
H–O–H
H–C–CH H–C=CH rds H–C–CH –CH–CH
2 2 2 3

O O O
OH OH

H–C–CH=CH–CH3
–OH
H–C=CH–CH–CH3 H–C–CH–CH–CH3

OH O H
O O
Aldols are stable and may be isolated. They, however can be dehydrated easily by heating the basic
reaction mixture or by a separate acid catalyzed reaction. Thus if the above reaction is heated the
product is dehydrated to 2-butenal (crotonaldehyde).
Acid catalysed Aldol
In acid catalysed aldol condensation enol form of carbonyl is the nucelophile in place of enolate.
Mechanism :
O +
O
H / H2O,
CH3–C–CH3 CH3–C=CH–C–CH3
CH3
( unsaturated

carbonyl compound)
O O–H OH
+
H
CH3–C–CH3 CH3–C–CH3 CH3–C=CH2
 
O–H O–H O–H OH
CH3–C=CH2 + CH3–C–CH3 CH3–C—CH2–C–CH3


–H
CH3

O O OH2 O OH

H
CH3–C–CH=C–CH3 CH3–C—CH–C–CH3 CH3–C—CH2–C–CH3
–H2O
CH3 H CH3 CH3
(Aldol)
Q.1 Write the product and mechanism for given reactions.

(I) CH 3  CH 2  C  H Dil
NaOH
 (A) 
 (B)
||
O
(II) O Dil
NaOH
 (C)
(III) C6H5 – CH2– CHO Dil

NaOH
 (D)

(IV) O Dil
NaOH
 (E) 
 (F)

(V) C 6 H 5  C  CH 3 Dil
NaOH
 (G)  (H)
||
O
Q.2 Identify the intramolecular aldol product?
O O
|| || 
(I) CH 3  C  CH 2  CH 2  C  CH 3 Dil
NaOH
 (A) 
 (B)
O O
|| ||
(II) CH 3  C  CH 2  CH 2  CH 2  CH 2  C  CH 3 Dil
NaOH
 (C)
O O
|| ||
(III) CH 3  C  CH 2  CH 2  CH 2  C  CH 3 Dil
NaOH
 (D)
(IV) Dil
NaOH
 (E) 

(F)
O O
|| ||
(V) CH 3  C  CH 2  CH 2  CH 2  CH 2  CH 2  C  CH 3 Dil
 NaOH
 (G)

Q.3 Find out the total number of possible aldol products (including and excluding stereo products)
NaOH / HOH
(I) CH3–CHO + CH3–CH2–CHO  5 C

NaOH / HOH
(II) C6H5 –CHO + CH3–CHO  5 C

NaOH / HOH
(III) CH3–CHO + CH 3  C  CH 3  5 C

||
O
NaOH / HOH
(IV) CH3–CH = O + CH 3  CH 2  C  CH 3  5 C

||
O
NaOH / HOH
(V) C6H5 – CHO + CH 3  CH 2  C  CH 3  5 C

||
O
Q.4 Identify the structure of substrate?
O
Dil NaOH
(I) A   A=?
5 C
OH
OH
|
(II) A Dil
NaOH
 CH 3  C  CH 2 — C — CH 3 A=?
( 2 mole ) 5 C
|| |
O CH 3
Q.5 Complete reaction sequence:


(i ) OH
(i) (
i ) O 3 (1 eq )
  (a)  (b)
(ii ) Zn / H 2O (ii ) 

(i ) OH
(ii)  Product
( ii ) C6 H 5CHO
( iii ) 
O
Q.6 Complete the retro aldol and retro aldol condensation reactions :
O OH

OH CH3 CH–CH3
(i) (X) + (Y) 

O

OH
(ii) (X) 
CH3
OH
O

(i ) OH
(iii) [X] 
(ii ) 
(2) CLAISEN CONDENSATION
Esters undergo SNAE Reaction, when attacked by a Nu generated by the interaction of a base
(usually base related to the Alkoxy anion of ester) with one of the molecule of ester and this Nu attacks
on another molecule. The reaction over all is considered as condensation of esters known as claisen
ester condensation.
O O O
|| ( i ) RONa
| | ||
2Me  C  OR     Me  C  CH 2  C  OR
(ii ) Acidification
(-keto ester)
Mechanism :
O
|| RO  Na

(rds)
CH 3  C  OR
 ROH
 
O O O

 RO Na
Na Me–C=CH–COOR Me–C–CH=C–OR
Acidification
O O
|| ||
Me  C  CH 2  C  OR
Some times, when two ester groups are present within the molecule then the condensation occurs
intramolecule then cyclization caused thus is known as Dieckmann cyclization or Dieckmann's
condensation.
(i ) EtOK
Q.1 MeCOOEt    A
( ii ) Acidificat ion
(i ) MeOK
Q.2 EtCOOMe     B
(ii ) Acidificat ion
( i ) MeOK
Q.3 MeCOOMe + EtCOOMe    C
2 5 ( i ) C H ONa
Q.4 + CH3COOC2H5    D + D’
COOC 2 H 5
( i ) C 2 H5ONa
Q.5 | + C6H5CH2COOC2H5    E
COOC 2 H 5 ( ii ) Acidificat ion
(i ) PhONa
Q.6    F
CH2CH2COOEt
(i ) C H ONa 
Q.7 C2H5 – N     G H
2 5 3O
 H (Piperidone derivative)
( ii ) Acidificat ion 
CH2CH2COOEt
( i ) NaOEt in EtOH
Q.8      I
(ii ) Acidificat ion

Q.9 NaOEt
 J H
3O
 K

COOC 2 H 5 COOC2H5

( i ) C 2 H5ONa H 3O
Q.10 | +    L   M
COOC 2 H 5 COOC2H5 ( ii ) Acidificat ion 
Diethyl-, -Dimethyl
Glutarate
(3) PERKIN CONDENSATION
In Perkin reaction, condensation has been effected between aromatic aldehydes and aliphatic acid
anhydrides in the presence of sodium or potassium salt of corresponding acid of that anhydride, to yield
, -unsaturated aromatic acids.
C6H5–CHO + CH 3  C  O  C  CH 3 (
i ) CH 3COONa ,
   C6H5 – CH = CH – COOH + CH3COOH
|| || (ii ) H  / H 2O ,
O O
Mech.
( i ) ( CH CH CO ) O / CH CH COONa , 
Q.1 H3C CHO  3 
2
2  3  

2
  A
( ii ) H / H 2O , 
(
i ) ( CH 3CO ) 2 O / CH 3COONa , 
Q.2        B  
 C

( ii ) H 3O
Q.3 (
i ) ( CH 3CO ) 2 O / CH 3COONa ,
       D
( ii ) H  / H 2O ,
(
i ) Sodium Succinate ,
Q.4 C6 H5  C  H +      E
|| (ii ) H 3O 
O
( i ) MeCOONa
( ii ) H 3O  , 
Q.5 + F   
(4) KNOEVENAGEL REACTION
Reaction of active methylene group with aldehyde & Ketones is known as knoevenagel reaction.

( i ) H 2O / H
RCHO+ Pyridine
  RCH = C(COOR)2     R  CH  CH  COOH
or piperidine (ii )  ,  CO 2
Z can be
O
||
CHO, COOMe, CN, NO2, C  R , SOR, SO2R, SO2OR etc.
Mechanism:
  
R 3 N + H2C(COOR)2  R 3 N H  HC(COOR ) 2

H 2O


( i ) H 2O / H
R–CH = C(COOR)2     R – CH = CHCOOH
(ii )  ,  CO 2
High reactivity of the methylene group of the active methylene compound prevents self-condensation of
the aldehyde.
( i ) Pip
Q.1 CH3CHO + H2C(COOR)2  A
(ii ) H 3O , 
( i ) Pip
Q.2 C6H5CHO + H2C(COOR)2  B
( ii ) H 3O , 
( i ) Pip
Q.3 HOOC  CHO + H2C(COOR)2  C
Glyoxalic acid (ii ) H 3O , 
O
||
Q.4 Ph  C  H + Et
2 NH
 D

O
|| n C H NH
Q.5 Ph  C  H + CH3–NO2 5112  E

O
||
CH 3C NH 2
Q.6 +  F
  
CH 3COOH ,
O
|| NaOEt
Q.7 + Ph  C  H  G
(5) REFORMATSKY REACTION
-halo esters when treated with Zn in gives organometallic halo ester which provides the attacking Nu
for the another reactant, which is a carbonyl compound. When Nu attacks on carbonyl compound it
gives an intermediate which upon acidic hydrolysis followed by heating, results in formation of -
unsaturated acid. The overall reaction is known as Reformatsky reaction.
O
|| Zn
Ph – CHO + CH 2  C  OEt  Ph – CH = CH – COOH
| H 3O  / 
Br
Benzaldehyde Cinnamic acid
Mechanism :

O O ZnBr
|| |
Zn Ph–CH
CH 2  COOEt  CH2– COOEt Ph–CH–CH2–COOEt
| | 
Br ZnBr H3O
OH
Br |
EtOH + Zn + Ph–CH–CH2–COOH
OH /–H O 2
Ph–CH=CH–COOH
Cinnamic acid
1. Zn
Q.1 C6H5COCH3 + BrCH2COOEt  A
2. H 3 O , 
(i ) Zn
Q.2 (
ii ) PhCHO
  B
(iii ) H3O ,
Q.3 + CH3CHO (

i ) Zn / Ether
  C

( ii ) H 3O ,
1. Zn Se
Q.4 + BrCH2COOEt  
D  E
2. H3O 
Br
|
Se
Q.5 EtO  C  CH  CH 2CH 2CH 2  CH 2  CHO (
i ) Zn / Et 2 O
  F  G
|| ( ii ) H 3O  
O
Q.6 (
i ) Zn / Et 2O
  H
(ii ) CH2 O
(iii ) H3O ,
(1) Zn + BrCHCH = CH – COOCH 3 (1) SOCl2 (1) Zn + BrCH2COOEt

Q.7  I (2) CH Li J  K
(2) H3O (3) , – H 2O 3 (2) H 3O (3) , – H 2O
LiAlH4
CH2OH
Vitamin A1
(6) CANNIZARO REACTION

This reaction is given by aldehyde having no  - hydrogens in the presence of conc. NaOH/ or KOH/.
O O
|| ||
KOH
H  C  H  H  C  O  K+ + CH3OH

Mechanism :
O O
O O || ||
r.d.s 
H–C–H C CH 3 – O + H–C–O–H  CH 3OH H – C – O 
+
OH H H
In the presence of a very strong concentration of alkali, aldehyde first forms a doubly charged anion (I)
from which a hydride anion is transferred to the second molecule of the aldehyde to form acid and an
alkoxide ion. Subsequently, the alkoxide ion acquires a proton from the solvent.
O 
O 
O
OH OH
H–C H–C–H H–C–H
(I)
H OH O

  H
O H O

H–C–H +C=O H–C + H–C–O
(I)
O H O H

 H2O 
HCH2O From solvent HCH2OH + OH
Q.1 Which of following will not undergo Cannizaro reaction
(A) (B) (C) (D) Cl3C–CHO
O
|| H2
Q.2 Ph – C  Cl  Ph – CHO HCHO
  (C) + (D)
Pd  BaSO 4  , KOH
Product (C) & (D) are
(A) Ph–CO2H, Ph–OH (B) Ph – CO 2– , HCO 2–
(C) Ph–CH2OH, H – CO 2– (D) Ph – CO 2– , CH3OH
CHO H
conc . NaOH
Q.3 |   (A)  (B)

CHO
Product (B) is
O
||
CH 2  O  C
(A) H2C=CH–CO2H (B) (C) | | (D) H2C=C=O
CH 2  O  C
||
O
NaOD NaOD
Q.4 (i) HCHO  (ii) DCHO 
 18
Q.5 (i) Ph–CHO O D / DOD
   (ii) Ph–CHO OH


 
KOH KOH
Q.6 (i) Ph–CHO + HCHO 

(ii) Ph  C  C  H 

| | ||
O O
KOH conc. KOH
Q.7 (i) MeCH2 – CHO 

(ii) Me2CH–CHO  

Q.8 (i) Me–NO2 + HCHO KOH

 (ii) Me–CHO + HCHO KOH

(excess ) (excess )
(7) BENZIL-BENZILIC REARRANGEMENT OR BENZILIC ACID REARRANGEMENT
The base catalysed reaction of 1, 2-diketones to a salt of -2-hydroxy carboxylic acid is known as
Benzilic acid rearrangement, this reaction is mainly applicable when aryl group is present on both carbonyl
carbons.
O OH
|| |
Ph – C – C – Ph (i ) OH ¯

 HO – C – C – Ph
|| (ii ) H  || |
O O Ph
(Benzil) (Benzilic acid)
Mechanism :
O OH O O
||  | ||
OH |
Ph – C – C – Ph Ph – C – C – Ph  HO – C – C – Ph
|| | || |
O O O Ph
OH OH
|  |
HO – C – C – Ph H 
O – C – C – Ph
|| | || |
O Ph O Ph
(Benzilic acid)
O O
|| ||
Q.1 CH3 C – C – C6H5 OH
O O
|| ||
1
. NaOH
C–C 
Q.2 O O 2, H 
(Furil)
O O
|| || (i) OH 
Q.3 Ph  CH 2  C  C  C6 H 5 
(ii) HOH / H
O OH
|| | Fenton (i) OH 
Q.4 C6 H 5  C  CH  C6 H 5    A  B.
reagent
(ii) HOH / H
O
(i) NaOH
Q.5 
(ii) H3O
O
O
(i) NaOH
Q.6 
O (ii) H3O
(8) MICHAEL ADDITION
Michael Addition :  unsaturated carbonyl compound undergo michael reaction with compounds
having active methylene. Many different nucleophile can add to  unsaturated carbonyl compound.
When the nucleophile is an enolate the addition reaction has a special name MICHAEL REACTION.
Mechanism :
O
||
O O  O O R – CH= CH

– C –R
|| || OH (base) || || 
R – C – CH2 – C – R R – C – CH – C –R  unsaturated

– H2O 
carbonyl compound
O O 
O O
R–C R–C
HOH
CH – CH – CH2 – C – R CH – CH – CH = C – R
R–C – OH  R–C
R R
O O
O O O
|| 
|| || OH
Q.1 CH3 – C – CH2 – C – CH3 + CH2 = CH – CH ?
– H2O
O
|| COOEt
CH CH O 
Q.2 CH 3CH  CH  C  CH 3 + CH2 3 
2
 ?
COOEt
O O O
|| || ||
O
Q.3 CH 3CH  CH  C  NH 2 + CH 3  CH 2  C  CH 2  C  O  CH 3 CH
3  ?
O O
|| || CH O 
Q.4 CH 3CH 2 CH  CH  C  OCH 3 + CH 3  C  CH 2  C  N 3  ?
O COOR  
Q.5 CH–CH3 + CH2 EtO
 Na
 ?

(ii ) H 3O ,
COOR
(9) TISCHENKO REACTION / TISCHENKO CONDENSATION
(1) This reaction takes place between two molecules of aldehydes.
(2) Reaction is catalysed by aluminium ethoxide.
(3) This is a two-step reaction, i.e., redox reaction followed by ester formation. Thus this reaction is
extension of Cannizzaro reaction.
O
( C 2 H5O )3 Al||
R – CHO + R – CHO    R  CH 2  O  C  R
Mechanism :
H H
|   |
R–CH=O  
R – C = O + Al(OC2 H5)3  R–C=O–Al (OC2H5)3 R–CH = O – C – O – Al(OC2 H5)3
|
H R
Hydride ion
transfer
O
||
R – CH2 – O – C – R + Al(OC2H5)3
Ester
( C 2 H 5O )3 Al
Q.1 CH3 – CHO   ?
( C 2H 5O ) 3 Al
Q.2 CH3–CH2–CHO   ?
( C 2 H 5O )3 Al
Q.3 OHC – CH2–CH2 – CH2 – CHO   ?
( C 2H 5O ) 3 Al
Q.4 CH3–CH2 – CH2 – CH2 – CHO   ?
(10) COREY HOUSE SYNTHESIS
Reaction of Gilman’s reagent with alkyl halide gives alkane as one of the product which is known as
Corey House synthesis,
  R' – X
[R2Cu] Li 
R' – R + RCu + LiX
Gilman reagent
(Lithium dialkyl cuprate)
To obtained good yield of alkane, the alkyl halide R’–X must be either a methyl halide, a primary alkyl
halide, or a secondary cycloalkyl halide.(Best CH 3X, if possible)
Preparation of Gilman reagent:

 
R – X 2
Li
 R Li Cu
X ,
 [R 2Cu] Li
 Li X (2 mole) Li X Gilman reagent
(alkyl Lith ium)
Complete the following reaction sequence :

Li CH CH CH CH CH I
Q.1 CH3– I  (A) CuI
 (B) 3 
 2 2
 2 
2
 (C)
Et 2O  
Li
CH3CH2CH2CH2Br  (D) CuI


Et 2O 
CH CH CH CH CH Br
(E) 3 
2 2
 22
 (F)

Li CH3Cl
Q.2 (A) Cl

CuCl
2  (B)  (C)  (D)   CH 3  CH  CH 2  CH 3
h   |
CH 3
( i ) Li CH 3 Cl
Q.3 CH3 – CH2 – Br  (A)    (B)
(ii ) CuBr ,  
(i ) Li 3 CH CH  Br
Q.4 I  (A)   2 (B)
(ii ) CuI 

CH3 CH CH3

|
Cl
(C)
CuBr O
Q.5 Li
CH3 – CH2 – Br  (A) (B)
(i)

(D)
(ii) H
Q.6 How can you prepare following compounds using corey house synthesis.
(i) CH3 (ii) CH2 = CH – CH2 – CH3
(iii) CH2
14
Q.7 (CH3)2CuLi + CH 2  CH  C H 2  Cl 

Q.8 (CH3)2CuLi + CH3 – CH – CH2  (A) H
 (B)
O
O
||

Q.9 (CH3)2CuLi +  (A) H
 (B)

Q.10 (CH3)2CuLi + CH 2  CH  C  H  (A) H
 (B)
||
O
Q.11 Which of the combination of Gilman’s reagent & alkylhalide will be most suitable for preparation of
following compounds.
CH 3 CH 3
| |
(i) CH3 – CH2 – CH3 (ii) CH 3  C  CH 3 (iii) CH 3  C  Ph
| |
CH 3 CH 3
(iv) (v)
Q.12 Identify the product of following reactions:

CH 2
|| 
(a) CH 3  C  CH 2  Cl  (CH 3 ) 2 CuLi (b)
14
(11) OZONOLYSIS
The reaction of alkene or Alkyne with ozone (O3) followed by hydrolysis is known as ozonolysis.
It is two types : (I) Reductive ozonolysis  In presence of reducing agent
(II) Oxidative ozonolysis  In presence of oxidising agent
Reducing agents : Zn, H2O or Zn, CH3COOH or (CH3)2S or (Ph)3P etc.
Oxidising agents : H2O2 or R  C  O  O  H or Ag2O etc.
||
O
R R’ R O R’ Zn / H O R
O3 2
C=C C C Reductive C=O + R’–C–H
step I
R H –70°C R H ozonolysis R
O O O
Oxidative [SCT- Cut the double bond

Example 1 : ozonolysis H2O2 and paste two oxgen atoms
and vice versa]
R–C–R + R’–C–OH
O O
Mechanism :
R
 R
R R O R C O R’
O
C 
O C O

+ C=O
+ O R 
C R’ C O H
R’ H O
H
R
R
O  R—C—O
C O
R  O
R’ R–C–R + R’–C–H
O
O=C C
H R’ O O
H
Note : In case of oxidative ozonolysis aldehyde (not ketone) further undergoes oxidation which gives
acid as product.
Q.1 Give the product of the following reaction.

(i) H2C = CH2 (
i ) O3
 (ii) CH3–CH = CH2 (
i ) O3

(ii ) Zn / H 2O (ii ) Zn / H 2O
CH 3
|
(iii) CH 3  C  CH 2 (
i ) O3
 (iv) (
i ) O3

(ii ) Zn / H 2O (ii ) Zn / H 2O
(v) (
i ) O3
 (vi) (
i ) O3

(ii ) Zn / H 2O (ii ) Zn / H 2O
H
(vii) H2C=CH–CH2–CH=CH–CH3 (
i ) O3

(ii ) Zn / H 2O
Q.2 Find out the structure of reactant.
H
(i ) O3 (i ) O3 O + O
(i) X  CH 3  CH 2  C  H (ii) X 
(ii ) Zn / H 2O || (ii ) Zn / H 2O H
O
H O
O O
(i ) O3 (i ) O3
(iii) X  O+ (iv) X  +
(ii ) Zn / H 2O (ii ) Zn / H 2O
H H
O
CH3 H
(v) X (
i ) O3
 O (vi) X (
i ) O3
 + C=O + C=O
(ii ) Zn / H 2O (ii ) Zn / H 2O
H3C H
O
O
O
(vii) X (
i ) O3
 (viii) X ( i ) O3
 O + HCHO
(ii ) Zn / H 2O (ii ) Zn / H 2O
O C10 H12
O
O
O
(ix) X ( i ) O3
 + O=C=O + O + HCHO
(ii ) Zn / H 2O
C12 H18
O O
(x) C 6 H 4 ( i ) O3
 C3H2O3 (xi) X 3 
(i ) O
+ HCHO
( X) ( ii ) Zn / H 2O (ii ) Zn / H 2O
C12 H18
O
Q.3 Give the ozonolysis product of the following.
H
O3 (  ) O3
(i) X   3 O C H (ii)  ?
Zn Zn / H 2 O
O
How many species.
(iii) O
3/

Zn / H 2 O
How many species are found.
Q.4 How mnay ozonoids are possible in given reaction.

(i ) O3 (i ) O3
(i) CH2 = CH2  
(ii ) Zn / H O
(ii) CH3 – CH = CH – CH3  
(ii ) Zn / H O
2 2
(i ) O3
(iii) CH3 – CH = CH2  
(ii ) Zn / H O 2
Q.5 The reactants that lead to product (a) and (b) on ozonolysis are
HCHO
(a) (b)
(A) (B)
(C) (D)
Q.6 Which starting material should be used to produce the compound shown below?
3 O
? 
Zn  H 2O
(A) (B) (C) (D)
Q.7 This compound on ozonolysis gives which of the following compounds
O
||
(I) (II) OHC  C  C  CH 2  C  CHO
|| ||
O O
O
||
(III) CHO (IV) OHC  C  C  CH 2  CH  O
| ||
CHO O
(A) I, II, III & IV (B) I, III, IV (C) I, II, III (D) I, II, IV
(12) OXYMERCURATION-DEMERCURATION
OMDM is a hydration process of alkene according to Markovnikov’s rule with no rearrangement of cyclic
mercuinium ion. When reaction with that reagent is complete, sodium borohydride and hydroxide ion are added
to the reaction mixture.
(i ) Hg ( OAC ) 2 , H 2O,THF
R–CH = CH2       R  CH  CH 3
(ii ) NaBH4 ,HO ¯
|
OH
(i)Hg(OAc)2, MeOH, THF
R  CH  CH 3
(ii) NaBH 4, HO¯ |
OMe
Mechanism for oxymercuration:
OAc
OAc +
Hg
H2 O
CH3CH = CH2 + Hg — OAc CH3CH — CH2 CH3CHCH2—Hg—OAc
+
OH
+ AcO¯
H
¯OAc
CH3CHCH2—Hg—OAc
OH + AcOH
Sodium borohydride (NaBH4) converts the carbon-mercury bond into a carbon-hydrogen bond. Because
the reaction results in the loss of mercury, it is called demercuration.
CH 3CHCH 2 —Hg—OAc NaBH
 4  CH 3CHCH 3 + Hg + AcO¯
HO ¯
| |
OH OH
Q.1 (
i ) Hg ( OCOCH 3 ) CH 3OH
     Q.2 (
i ) Hg ( OAc ) 2 , H 2O
   

(ii ) NaBH 4 ,OH (ii ) NaBH 4 ,OH 
CH3
(
i ) Hg (CF3COO )2 ,CH 3OH
    
Q.3 ( ii ) NaBH 4 , HO ¯ Q.4 (
i ) Hg (OAc ) 2 ,CH3  O H
    
(ii ) NaBH4 ,OH 
CCH
OH
Q.5 (
i ) Hg ( OAc ) 2 , H 2O
    Q.6 (
i ) Hg ( OAc ) 2 , H 2O
   

Q.7 How could each of the following compounds be synthesized from an alkene by OMDM?
OH OCH2CH3 CH 3 CH 3
| |
(i) (ii) (iii) CH 3CCH 2CH 3 (iv) CH 3CCH 2CH 3
| |
OH OCH 3
(13) HYDROBORATION-OXIDATION
Hydroboration has been developed by brown as a reaction of tremendous synthetic utility because alkyl
boranes are able to undergo a variety of transformation. Hydroboration is a one step, four centre, cis
addition process in accordance with Markovnikov’s rule but after oxidation it seems to be appear to
violate Markovnikov’s rule.
OH¯ ,H2 O2 , H2 O
Hydroboration oxidation
CH3CH2CH 2OH
( i ) BH 3 ,THF
CH3CH = CH2     (CH3CH2CH2)3 B CH3 COOH
Hydroboration reduction
CH3CH2CH 3
AgNO3
Dimerisation, 
CH3CH2CH 2 CH2CH2CH 3
NH2Cl
CH3CH2CH 2–NH2
Cl2
CH3CH2CH 2–Cl
Mechanism of Hydroboration:
H H
+
CH3CH=CH2  CH3—C—C—H  CH 3CH 2CH 2 2
(CH3CH2CH2)3 B
|
H—BH2 H BH2 BH 2
—
an alkylboran e
More stable
transition state
Mechanism of oxidation :
HOOH + HO¯  HOO¯ + H2O
R R R repeat the two

preceding steps
OR
two times
R–B + O—OH R—B—O—OH R—B—OR RO—B—OR
R R HO¯
+ OH¯
OR
RO—B¯— OR
OH
repeat the two

preceding steps OR OR
3– two times
3 ROH + BO3 ROH + RO—B RO¯ + RO—B
O¯ O—H
(i ) BH
Q.1 CH2 = CH2  3  Q.2 (
i ) BH3 ,THF
 
(ii ) HO ¯,H 2O 2 (ii ) H 2O / AcOH
(i ) BH
Q.3  3  Q.4 (
i ) BH 3 ,THF
 
(ii ) HO ¯,H 2O 2 (ii ) H 2O / AcOH
CCH
(i)BD3, THF
Q.5 (ii)CH3COOH, H2 O Q.6 (
i ) BH3 ,THF
 
(i)BH3, THF (ii ) H 2O2 / HO 
(ii) CH3COOD, D2O

(i) BT3, THF
(ii) CH3COOD, D2O
CH = CH2 CH = CH2
Q.7 (
i ) BH 3 ,THF
  Q.8 (
i ) BH 3 ,THF
 
(ii ) NH 2Cl (ii ) AgNO 3 ,
CH = CH2
Q.9 (
i ) BH3 ,THF
  (i ) BH ,THF
Q.10 CH3–C CH  3  
(ii ) Cl 2 (ii ) AgNO3 ,
(14) RIEMMER TIEMENN REACTION
It is believed that chloroform and hydroxide ion react to produce an electron deficient intermediate
dichloro carbene : CCl2 (DCC)
—
OHH H2O + : :CCl2 + Cl
Treatment of phenol with DCC in basic medium introduces an aldehyde group, onto the aromatic ring.
This reaction is known as Reimmer Tiemenn reaction.

(i ) O H
   +
( ii ) :CCl 2 , ( iii ) H 
The Reimmer–Tiemenn reaction involves electrophilic substitution on highly reactive phenoxide ring. The
electrophilic reagent is dichloro carbene : CCl2
— 
+ :CCl2   O

H
  H
o-product is major product because :

(i) there are two o-positions available as compared to one para.
(ii) o-product is more stable due to the formation of six membered chelate formation.
If 1 ° amines (aliphatic and aromatic) react with DCC in basic medium it yield isocyanide or carbylamine.
This reaction is known as carbylamine reaction:
  

The product is known as isocyanide & it is a foul smelling substance.
Q.1 Step marked by is :

(A) Aromatization reaction (B) intramolecular acid base reaction
(C) both of the above (D) none of the above
Q.2 Addition of NaCl in aqueous solution will make Riemmer Tiemann reaction:
(A) slower (B) faster (C) no effect on rate (D) can't be predicted
Q.3 If is used instead of during Riemmer Tiemenn reaction the product formed is:
(A) (B) (C) (D)
Q.4 If CCl4 is used in place of CHCl3 during Riemmer Tiemenn reaction, the product formed is:
(A) (B) (C) (D)
Q.5 o/p ratio in Riemmer Tiemenn reaction follows following order, if NaOH & KOH are used one by one
as base
(A) NaOH = KOH (B) NaOH > KOH
(C) NaOH < KOH (D) can't be decided on the basic of information given here
Q.6 Which of the following will not give carbylamine reaction

(A) t-butyl amine (B) aniline (C) sec. butylamine (D) N-methyl methanamine
Q.7 Correct order of rate of carbylamine reaction for following compounds is:
(I) (II) (III)

(A) I > II > III (B) II > I > III (C) II > III > I (D) III > I > II
Q.8 Rate of carbylamine reaction for Me–NH2 will be :

(A) CHF3 > CHCl3 (B) CHCl3 = CHF3 (C) CHCl3  CHF3 (D) CHF3 < CHCl3
(1) ALDOL CONDENSATION

OH
|
Q.1 (I) (A) CH 3  CH 2  CH  CH  C  H
| ||
CH 3 O
(B) CH 3  CH 2  CH  C  C  H
| ||
CH 3 O
O OH
(II) (C)
Ph
|
(III) (D) Ph  CH 2  CH  CH  C  H
| ||
OH O
O OH O
(IV) (E) (F)
CH 3 CH 3
| |
(V) (G) Ph  C  CH 2  C  Ph (H) Ph  C  CH  C  Ph
| || ||
OH O O
O O
Q.2 (I) (A) (B)

HO
CH3 OH
(II) (C) C—CH3
O
O
(III) (D) OH
CH3
O O
(IV) (E) (F)

OH
CH3
(V) (G)
C—CH3
O
Q.3 Excluding Stereo Including Stereo
(I) 4 12
(II) 2 4
(III) 4 6
(IV) 6 16
(V) 4 12
OH
|
(I) Me  CH  CH 2  CHO = 2
*
* *
Me  CH  CH  CHO
| | = 4
OH CH 3
*  CH  CHO
Et  CH 2
| = 2
OH
* *
Et  CH  CH  CHO
| | = 4
OH CH 3
OH
|
(II) Ph  CH  CH 2  CHO = 2
*
OH
|
Me  CH  CH 2  CHO = 2
*
OH
|
(III) CH 3  CH  CH 2  CHO = 2
*
OH
|
CH 3  C  CH 2  CHO
| = 1
CH 3
OH
|
CH 3  C  CH 2  COCH 3
| = 1
CH 3
OH
|
CH 3  CH  CH 2  COCH 3 = 2
*
OH
| *
(IV) CH 3  CH  CH  COCH 3 = 4
* |
CH 3
OH
|
CH 3  CH  CH 2  CHO = 2
*
OH
| *
CH 3  C ——— CH  COCH 3 = 4
*| |
CH 2CH 3 CH 3
OH
|
CH 3  CH  CH 2  CO  CH 3 = 2
*
OH
|
CH 3  CH  CH 2  COCH 2CH 3 = 2
*|
CH 2CH 3
OH
|
CH 3  C  CH 2  CHO
*| = 2
CH 2  CH 3
OH
|
(V) *  COCH
Ph  CH  CH = 4
3
* |
CH 3
OH
|
Ph  CH  CH 2  COCH 2 CH 3 = 2
*
OH
|
Me  C  CH 2  CO  Et
|* = 2
Et
OH
| *
Me  C — CH – COCH 3
*| | = 4
Et CH 3
O
||
Q.4 (I) (II) CH 3  C  CH 3

|| ||
O O
O
||
C–H
Q.5 (i) (a) (b) C – H (ii) CH—C6H5
||
CH2 – CH2 – C – H O
|| O
O
O
CH3 ||
Q.6 (i) X = Y = CH 3  C  H
||
O O O
|| ||
(ii) X = CH 3  C  CH 2  CH 2  C  CH 3
O
||
(iii) X = CH 3  C  CH 2  CH 2  CH 2  CHO
(2) CLAISEN CONDENSATION

O O O O
|| || || * ||
Q.1 Me  C  CH 2  C  OEt Q.2 Et  C  CH  C  OMe
|
CH 3
(R / S)
Q.3 4 products Q.4 , CH3 COCH2 COOC2H5
O
* C—OPh
Q.5 Q.6
O
(R/S)
COOEt
Q.7 (G) C H – N O , (H)

2 5
O
COOH
C–O Et
O O
Q.8 Q.9 (J) (K)
C–O Et
COOH
O
O
O C–OC2H5 O
O
Q.10 (L) (M) 
H
O C–OC2H5 O O
O enol is more stable
(3) PERKIN CONDENSATION
OH O O
Q.1 H3C CH  C  COOH Q.2
|
CH–CH2–COOH
CH 3 |
(B) OH (C)
OH O
Q.3 CH=CH–COOH Q.4 C6H5 – CH – CH C OH
H2 C C OH
O
O O
|| ||
Q.5 Me  C  O  C  Me
(4) KNOEVENAGEL REACTION

Q.1 CH 3  CH  CH  COOH Q.2 C 6 H 5  CH  CH  COOH
Crotonic acid Cinnamic acid
Q.3 HOOC  CH  CH  COOH Q.4 Ph – CH=

Maleic acid
Q.5 Ph – CH = CH – NO2 Q.6
Q.7 = CH–Ph
(5) REFORMATSKY REACTION

Ph  CH  C  COOH
Q.1 C6H5–C=CH–COOH Q.2 |
|
CH3 CH 3
(E/Z) ( E / Z)
HO CH2COOH
CH–CH3
Q.3 Ph Q.4 (D) , (E)
OH
O
COOH COOH
OH
Q.5 (F) (G)
Q.7 (I) , (J) ,
(K) ,
(6) CANNIZARO REACTION
Q.1 D Q.2 C Q.3 B
Q.4 (i) CH3OD + HCOONa (ii) DCH2OD + DCOONa
18
Q.5 (i) PhCH2OD + PhCOONa (ii) Ph–CH2OH + PhCOONa
Q.6 (i) Ph–CH2OH + HCOOK (ii) Ph  CH  C  OK

| ||
OH O
O
||
Q.7 (i) MeCH 2  CH  C  C  H (ii) Me2CH – CH2OH + Me2CHCOOK
|
Me
OH OH
OH OH
NO2 + CH3OH + HCOOK
Q.8 (i) (ii)
HO + HCOOK HO OH
(7) BENZIL-BENZILIC REARRANGEMENT OR BENZILIC ACID REARRANGEMENT
OH
OH |
|  C
Q.1 CH3 C – COO Q.2 O | O
| COOH
C6H5
(Furilic acid)
O O OH
OH || || |
Q.3 Ph – CH2 – C Q.4 (A) Ph  C  C  Ph (B) Ph  C  COOH
| COOH |
C6H5 Ph
OH OH
Q.5 Q.6
COOH COOH
(8) MICHAEL ADDITION

O
|| O
CH2 – CH2 – CH
| CH3–CH–CH2–C–CH3
Q.1 CH3 – C – CH – C – CH3 Q.2 O
|| ||
O O CH(–C–OCH2CH3)2
O O
CH3–CH–CH2–C–NH2 CH3–CH2–CH–CH2–C–O–CH3
Q.3 O O Q.4
CH3 – CH2 – C–CH–C–O–CH3 CH3–C–CH–CN
O
O
CH–CH2 – COOH
Q.5 CH3
(9) TISCHENKO REACTION / TISCHENKO CONDENSATION

O O
|| ||
Q.1 CH 3  C  O  C 2 H 5 Q.2 CH 3  CH 2  C  O  CH 2  CH 2  CH 3
O
Q.3 O
O
||
Q.4 CH 3  CH 2  CH 2  CH 2  C  O  CH 2  CH 2  CH 2  CH 2  CH 3
(10) COREY HOUSE SYNTHESIS

Q.1 (A) CH3Li, (B) (CH3)2CuLi, (C) CH3–CH2CH2CH2CH2CH3, (D)CH3CH2CH2CH2Li,
(E) (CH3CH2CH2CH2)2CuLi , (F) CH3CH2CH2CH2– CH2CH2CH2CH2CH3
Q.2 (A) CH3–CH2–CH3 (B) CH 3  CH  CH 2  Cl

|
CH 3

 
(C) CH 3  CH  CH 2Li (D) CH 3  CH  CH 2  CuLi 
|  | 
CH 3  CH 3 3
Q.3 (A) [CH 3CH 2 ]2 Cu Li (B) CH3 – CH2 – CH3


Cu Li CH2–CH3
Q.4 (A) (B)
2
Et
  |
Q.5 (A) CH 3  CH 2 Li (B) [CH 3CH 2 ]
2 Cu Li

(C) CH 3  CH  CH 3
(D)
Et
Q.6 (i) [Ph ]  CH 3 Cl
2 CuLi    Ph–CH3
  CH 3–Cl
(ii) [CH2=CH–CH2] CuLi CH2–CH–CH2–CH3
2
  Ph – CH2– Cl
(iii) [Ph] CuLi Ph–CH2–Ph
2
14
Q.7 CH 3  CH 2  CH  CH 2
Q.8 (A) CH 3  CH  CH 2  CH 3 (B) CH 3  CH  CH 2  CH 3

| |
O  Li  OH
 
O Li O
Q.9 (A) (B)

CH3 CH3
Q.10 (A) CH 3  CH 2  CH  C  H (B) CH 3  CH 2  CH 2  C  H

| ||

OLi  O
Q.11 (i) [CH 3  CH 2 ]2 CuLi  + CH3 – Cl (ii) [ Me 3C]2 CuLi  + CH3 – Cl
Ph
(iii) Me C– CuLi + Me–Cl (iv) CuLi + Me–Cl
Me
2
(v) CuLi + Me–Cl
CH 3
|
Q.12 (a) CH 3  C  CH 2  CH 3 (b) CH 3  CH 2  C  CH  CH  CH 3
|| |
CH 2 OLi
14
(11) OZONOLYSIS
O H CH3
H H || H
Q.1 (i) O + O=C (ii) CH 3  C  H + C=O (iii) CH + C=O
H H H 3 H
O
O O
H
(iv) H H (v)
O O
O O
H
(vi) +H (vii) C=O + O  C  CH 2  C  O + O  C  CH 3
O O H | | |
H H H
H
H H H
Q.2 (i) (ii) (iii)
H
(iv) H (v) (vi)
CH3
C=C—C=CH2
(vii) (viii) (ix) CH3
(x) (xi)
CH3 O O O
CH3 H
H O C C C
Q.3 (i) (ii) (iii) + +
C C C
O CH3 O H H
O O
Q.4 (i) 1
(ii) 3
(iii) 6
Q.5 (A, B, C) Q.6 (B) Q.7 (C)
(12) OXYMERCURATION-DEMERCURATION
OCH3 OH H3C OCH3

Q.1 Q.2 Q.3
COCH3
OCH3
O
Q.4 Q.5 Q.6
OH OCH2CH3
Q.7 (i) (

i ) Hg ( OAc ) 2 , H 2O
    (ii) (
i ) Hg ( OAc ) 2 ,CH 3CH 2OH
    

CH 3
|
(iii) (
i ) Hg ( OAc ) 2 , H 2O
    CH 3CCH 2CH 3
(ii ) NaBH 4 ,OH  |
OH
CH 3
|
(iv) (
i ) Hg ( OAc ) 2 ,CH 3OH
     CH 3CCH 2CH 3
(ii ) NaBH 4 ,OH  |
OCH 3
(13) HYDROBORATION-OXIDATION
H H
Q.1 CH3CH2OH Q.2
H OH
CH3 H OH CH3
H CH3 CH3 OH
Q.3 OH , H ] Q.4 CH3 , H ]
H OH H CH3
CH2D CH2D
Q.5 (i) CH 3  CH  CH 2 , (ii) CH 3  CH  CH 2 , (iii) H T T H ]
| | | |
D H H D CH3 CH3
CH2CHO CH2–CH2–NH2
Q.6 Q.7 Q.8 (CH2)4
CH2–CH2–Cl
Q.9
Q.10 Z Z, E E, Z E of CH3–CH = CH–CH=CH–CH3
(14) RIEMMER TIEMENN REACTION
Q.1 (C)
 
Q.2 (A) Common ion effect will decrease concentration of C Cl 2
Q.3 (A) Abnormal Riemmer Tiemann reaction
Q.4 (D)
Q.5 (B) Due to bigger size of K+ it cannot fit in chelate that well.
Q.6 (D) D is 2° amine
Q.7 (B) Based on order of nucleophilicity

   
Q.8 (D) Order of electrophilicity C Cl 2 > C F2
BIOMOLECULES, POLYMERS & POC FINAL LAP - 2019
EXERCISE-I
BIOMOLECULES
Q.1 The commonest disaccharide has the molecular formula
(A) C10H18O9 (B) C10H20O10 (C) C18H22O11 (D) C12H22O11
Q.2 On complete hydrolysis of starch, we finally get

(A) Glucose (B) Fructose
(C) Glucose and fructose (D) Sucrose
Q.3 The term anomers of glucose refers to

(A) Isomers of glucose that differ in configurations at carbons one and four (C–1 and C-4)
(B) A mixture of (D)-glucose and (L)-glucose
(C) Enantiomers of glucose
(D) Isomers of glucose that differ in configuration at carbon one (C–1)
Q.4 Which of the following is an example of aldopentose?

(A) Erythrose (B) Ribose (C) Fructose (D) Dihydroxyacetone
Q.5 Glucose and fructose form

(A) Same osazone (B) Same acid on oxidation
(C) Same alcohol when reduced (D) Different osazone
Q.6 The change of optical rotation of glucose solution with time is refered to as:
(A) Mutarotation (B) Inversion (C) Specific rotation (D) Autorotation
Q.7 To become a carbohydrate a compound must contain at least:

(A) 2 carbon atoms (B) 3 carbon atoms (C) 4 carbon atoms (D) 6 carbon atoms
Q.8 Methyl--D-glucoside and methyl--D-glucoside are

(A) Epimers (B) Anomers
(C) Enantiomers (D) Conformational diastereomers
Q.9 The correct name of 'sucrose' is

(A) -D-glucopyranosyl--D-fructofuranoside
(B) -D-glucopyranosyl--D-fructofuranoside
(C) -D-glucopyranosyl--D-fructofuranoside
(D) -D-glucopyranosyl--D-fructofuranoside
Q.10 Which one of the following is laevorotatory

(A) Glucose (B) Sucrose (C) Fructose (D) None of these
Q.11 Which of the following is a disaccharide

(A) Lactose (B) Starch (C) Cellulose (D) Glucose
Q.12 The two functional groups present in a typical carbohydrate are
(A) – OH and – COOH (B) – CHO and – COOH
(C) > C = O and – OH (D) – OH and – CHO
Q.13 The monomer of cellulose is

(A) Fructose (B) Galactose (C) Glucose (D) None of these
Q.14 Glucose is a
(A) Monosaccharide (B) Disaccharide (C) Trisaccharide (D) Polysaccharide
Q.15 Which pair is different for reaction with Fehling solution:

(A) Glucose, Fructose (B) HCHO, CH3CHO
(C) CH3COCH3, C6H5CHO (D) Glucose, Sucrose
Q.16 Glucose contains in addition to aldehyde group

(A) One secondary OH and four primary OH groups
(B) One primary OH and four secondary OH groups
(C) Two primary OH and three secondary OH groups
(D) Three primary OH and two secondary OH groups
Q.17 Glucose reacts with excess of phenyl hydrazine and forms

(A) Glucosazone (B) Glucose phenyl hydrazine
(C) Glucose oxime (D) Sorbitol
Q.18 Which set of terms correctly identifies the carbohydrate shown

H O OH
OH H
HOH2C H
H OH
1. Pentose 2. Hexose
3. Aldose 4. Ketose
5. Pyranose 6. Furanose
(A) 1, 3 and 6 (B) 1, 3 and 5 (C) 1, 4 and 6 (D) 2, 3 and 6
Q.19 Hydrolysis of sucrose is called:

(A) Inhibition (B) Saponification (C) Inversion (D) Hydration
Q.20 Which of the following pentoses will be optically active
CHO CHO CHO

| | |
HCOH HCOH HCOH
| | |
HOCH HCOH HCOH
| | |
HCOH HOCH HCOH
| | |
H 2COH H 2COH H 2COH
I II III
(A) All (B) II and III (C) I (D) II

Q.21 The secondary structure of a protein refers to
(A) -helical backbone (B) Hydrophobic interactions
(C) Sequence of -amino acids (D) Fixed configuration of the polypeptide backbone
Q.22 A tripeptide is written as Glycine-Alanine-Glycine. The correct structure of the tripeptide is

O CH3
NH
(A) NH2 NH COOH
O CH3
CH3 O CH3
NH
(B) NH2 NH COOH
O
O
NH
(C) NH2 NH COOH
O CH3
CH3 O
NH
(D) NH2 NH COOH
O CH3
Q.23 Which compound can exist in a dipolar (zwitter ion) state

(A) C6H5CH2CH(N = CH2) COOH (B) (CH3)2CH·CH(NH2)COOH
(C) C6H5CONHCH2COOH (D) HOOC·CH2CH2COCOOH
Q.24 Which of the following statement is incorrect for maltose.

(A) It is a disaccharide (B) It undergoes mutarotation
(C) It is a reducing sugar (D) It does not have hemiacetal group.
Q.25 Identify the correct statement about lactose.

(A) It consists of one galactose and one glucose unit
(B) Mutarotation is not possible
(C) Anomeric carbon of galactose is attached to 4' carbon of glucose which is –1, 4'-glycoside bond.
(D) Lactase is not used to cleave the –1, 4'-glycoside bond.
Q.26 Which of the following carbohydrates would be most abundant in the diet of strict vegetarian?
(A) Amylose (B) Glycogen (C) Cellulose (D) Maltose
Q.27 Naturally occuring (+) - sucrose is :

(A) -D-glucopyronoside--D-fructofuranoside
(B) -D-glucopyronoside--D-fructofuranoside
(C) -D-glucopyronoside--D-fructofuranoside
(D) -D-glucopyronoside--D-fructofuranoside
Q.28 D-Ribose when treated with dilute HNO3 forms.
HO O
HO O
H OH
OH
(A) H , Achiral (B) HO H , Chiral
H OH
H OH
H OH
O O OH
HO
HO O HO O
H OH H OH
(C) HO H , Achiral (D) H OH , Chiral
H OH H OH
HO O O OH
Q.29 Consider the given process.

CHO CHOH CHO
H–C–OH C–OH HO–C–H
HO H OH¯ HO H OH¯ HO H
H OH H 2O H 2O
H OH H OH
H OH H OH H OH
CH2OH CH2OH CH2OH
(I) (II) (III)
and identify the incorrect statement.
(A) Configuration at C–2 is lost on enolisation
(B) I and III are epimers
(C) Proton transfer from water to C–1 converts ene diol to an aldose.
(D) D-glucose can isomerise to D-fructose through enol intermediate.

Q.30 Glucose (
i ) HCN / H 3O
   P
( ii ) P / HI
P is :
(A) n- heptanoic acid (B) 2-methyl hexanoic acid
(C) n-heptane (D) 2-methyl hexane
Q.31 When methyl D-glucopyranoside is treated with HIO4 how many moles of HIO4 are consumed with per
mole of the sugar ?
(A) 2 (B) 3 (C) 4 (D) 5
Q.32 The configuration of the C-2 epimer of D-glucose is-

(A) 2R, 3S, 4R, 5S (B)2S, 3S, 4R, 5R
(C) 2S, 3R, 4S, 5R (D)2R, 3S, 4R, 5R
Q.33 Mutarotation involves

(A) Racemisation (B)Diastereomerisation
(C) Optical resolution (D)Conformational inversion
Q.34 Same osazone derivative is obtained in case of D-glucose, D-Mannose and D-Fructose due to
(A) the same configuration at C-5
(B) the same constitution.
(C) the same constitution at C-1 and C-2
(D) The same constitution and same configuration at C-3, C-4, C-5 and C-6 but different constitution
and configuration at C-1 and C-2 which becomes identical by osazone formation.
NaBH4
Q.35 D(–) –Erythrose (P)
NaBH4
D(–) –Threose (R)
Which of the following statement is correct about P and R ?
(A) Both are optically active
(B) Both are optically inactive
(C) P is optically inactive and R is optically active
(D) Neither P nor R has asymmetric carbon.
Q.36 Which of the following compounds will not show mutarotation:

(A) -D (+) glucopyranose (B) -D(+) glucopyranose
(C) Methyl--D-glucopyranoside (D) -D(+) galactopyranose
Q.37 Amylose and cellulose both are linear polymers of glucose. The difference between them is:
(A) Amylose has  (1  4') linkage and cellulose has  (1  4') linkage
(B) Amylose has  (1  4') linkage and cellulose has  (1  4') linkage
(C) Amylose has  (1  4') linkage and cellulose has  (1  6') linkage
(D) Amylose has  (1  4') linkage and cellulose has  (1  6') linkage
Q.38 Glycogen on hydrolysis gives:

(A) Lactose and Glucose (B) Only Glucose
(C) Glucose and Fructose (D) Glucose and Maltose
Q.39 An example of disaccharide made up of two unit of the same monosaccharide.

(A) Maltose (B) Sucrose (C) lactose (D) None
Q.40 The colour of the precipitate formed when a reducing sugar is heated with Fehling solution is:
(A) Brown (B) Red (C) Blue (D) Green
Q.41 Osazone formation involves only 2 carbon atoms of glucose because of

(A) Oxidation (B) Chelation (C) Reduction (D) Hydrolysis
Q.42 Methyl--D-glucose and methyl --D-glucose are

(A) Epimers (B) Anomers (C) Enantiomers (D) Constitutional isomers
Q.43 Hydrolysis of lactose with dilute acid yield

(A) Equimolar mixture of D-glucose and D-glucose.
(B) Equimolar mixture of D-glucose and D-galactose.
(C) Equimolar mixture of D-glucose and D-fructose.
(D) Equimolar mixture of D-galactose and D-galactose.
Q.44 Celluose is a straight chain polysaccharide composed of
(A) D-glucose units joined by -glycosidic linkage
(B) D-glucose units joined by -glycosidic linkage
(C) D-galactose units joined by -glycosidic linkage
(D) D-galactose units joined by -glycosidic linkage
Q.45  - amino acid when heated with BaO forms -

(A)  - unsaturated acid (B) - unsaturated amine
(C) Carboxylic acid (D)Amine
COO¯
Q.46 The pH of the solution containing following zwitter ion species is NH3 H
R
(A) 4 (B)6 (C) 8 (D)9
Q.47 Peptide linkage is -

O O O O
(A) –C – O – (B)–C – NH2 (C) –C – NH– (D)–C – NH–NH2
Q.48 The monomer of nucleic acids are held together by

(A) Phosphoester linkage (B) Amide linkage
(C) Glycosidic linkage (D) Ester linkage
Q.49 Test used to identify peptide linkage in protein is:

(A) Biuret (B) Ninhydrin test (C) Molisch test (D) 2,4-DNP test
Q.50 Which one of the following structures represents the peptide chain:
H O H O H O
(A) –N–C–C–C–N–C–C–N–C–C–C– (B) –N–C–N–C–NH–C–NH–
H O H
H H H H
(C) –N–C–C–C–C–NH–C–C–C (D) –N–C–C–N–C–C–N–C–C–
O O O
Q.51 Among the following L-serine is:
COOH COOH
(A) H2N CH 2OH (B) HOCH2 H
H NH2
NH2 CH2OH
(C) H COOH (D) H2N H
CH2OH COOH
POLYMERS
Q.52 The monomer that undergo radical polymerisation most easily is

Me
(A) CH2=CH2 (B) C6H5CH=CH2 (C) CH2=C (D) CH3–CH=CH2
Me
Q.53 Select the incorrect statement about Nylon 2-nylon-6.

(A) It is a copolymer.
(B) It is biodegradable.
(C) It is an alternating polyamide.
(D) It is made up of CH 3  CH  COOH and H2N(CH2)5COOH.
|
NH 2
Q.54 The polymer formed as a result of following sequence of reaction is

Cu2Cl2 HCl (1 eq.) polymerisation
2HC  CH (A) (B) (C)
NH4Cl
(A) Saran (B) PVC (C) Neoprene (D) Chloroprene
Q.55 The monomer that can undergo radical, cationic and anionic polymerisation with equal ease -
(A) Me–C=CH2 (B) Ph–CH=CH2 (C) CH2 = CH2 (D) CH2=CH–CN
Me
Q.56 Protein is a polymer of:

(A) Glucose (B) Terephthalic acid (C) Amino acid (D) Glycol
Q.57 Enzymes are:

(A) Minerals (B) Oils (C) Fatty acids (D) Proteins
PRACTICAL ORGANIC CHEMISTRY

Q.58 Consider the reaction-
OH
(i) CHCl3+NaOH
+
P (major) + Q (Minor)
(ii) H3O
Mixture of P and Q can be best separated by -
(A) Steam distillation (B) Vacuum distillation
(C) Fractional distillation (D) Crystallisation
Q.59 Which of the following compound(s) will give blue colour when it is converted into Lassaigne's extract
and FeSO4 is added followed by FeCl3.
O
||
(I) (II) (III) NH2–OH (IV) NH 2  NH  C  NH 2
(A) I and IV (B) IV only (C) I, III & IV (D) I, II, III & IV
Q.60 Select reagent which is used in laboratory to differentiate 1°, 2° and 3° amines from each other:
(A) NaOH, I2 (B) PhSO2Cl (C) CHCl3 , KOH (D) CS2, HgCl2
EXERCISE II
BIOMOLEUCLES
Q.1 Carbohydrates may be :
(A) Sugars (B) Starch
(C) Polyhydroxy aldehyde/ ketones (D) Compounds that can be hydrolysed to sugar
Q.2 Select the correct statement:

(A) S-glyceraldehyde is also known as L-glyceraldehyde
(B) The configuration of the stereocenter most distant from the carbonyl group determines whether a
monosaccharide is D or L.
(C) Glucose and all naturally occurring sugars are D-sugars
(D) D-erythrose and D-threose are diastereomers.
Q.3 Select the incorrect statement.

(A) Monosaccharide are insoluble in organic solvents like diethyl ether.
(B) Anomers of a cyclic monosaccharides differ in the position of the OH group at the hemiacetal
carbon.
(C) D-ribose the OH group used to form the five membered furanose ring is located on C4.
(D) Aldopentoses and ketohexoses form pyranose rings in solution.
Q.4 The peptide bond is a key feature in :

(A) Vitamins (B) Proteins (C) Nucleotides (D) Polypeptides
Q.5 Which is not correct about monosaccharides.

(A) Optically active polyhydroxy carbonyl compounds.
(B) Fructose & glucose can not be distinguish by Br2/H2O
(C) Glucose and mannose are anomers
(D) Fructose & glucose can be distinguish by Fehling solution
Q.6 Which of the following is disaccharides ?

(A) Lactose (B) Sucrose (C) Cellulose (D) Maltose

(A) Proteins upon hydrolysis gives -amino acid only.
(B) Except glycine, all other naturally occuring -amino acids are optically active.
(C) In fibrous proteins polypeptide chains are held together by hydrogen and disulphide bonds.
(D) Fats upon hydrolysis gives -amino acids

(A) Coiling of polypeptide chain form fibrous protein.
(B) Quarternary structure of protein also exist.
(C) Lysine is an amino acid with basic side chain.

(D) The absolute configuration of H 3 N – CH(CH2OH)COO¯ (L-serine) is S.

(A) All proteins are polyamides formed by joining amino acids together.
(B) All L-amino acids except cysteine have the S-configuration.
(C) Proline is 1° amine consisting 6 membered ring.
(D) Proline is a 2° amine consisting of five membered ring.
Q.10 Select the correct option.
(A) Isoelectric point is the pH at which an amino acid exists primarily in its neutral form.
(B) Isoelectric point is the average of pK a values of -COOH amino - NH 3 groups [valid only for
neutral amino acid]
(C) Glycine is characterised by two pKa values.
(D) For neutral amino acid the concentration of zwitter ion is maximum at its isoelectric point.
Q.11 Amino acids are synthesised from.

(A) -Halo acids by reaction with NH3.
(B) Aldehydes by reaction with NH3 and cyanide ion followed by hydrolysis.
(C) Alkyl halides by reaction with the enolate anion derived from diethyl acetamidomalonate & hydrolysis.
(D) Alcohols by reaction with NH3 and CN¯ ion followed by hydroysis.
Q.12 Which of the following carbohydrates developes blue colour on treatment with iodine solution ?
(A) Glucose (B) Amylose (C) Starch (D) Fructose
Q.13 Which of the following are correct.

(A) Br2/H2O can be used to differentiate between aldose & ketose.
(B) All monosaccharides are reducing sugar
(C) Osazone formation destroys the configuration about C2 of an aldose but not effect the rest of
molecule
(D) Mono saccharides undergoes mutarotation.
Q.14 Match the column :

Column I Column II
(A) Sucrose (P) Two acetals
(B) Maltose (Q) No hemiacetal
(C) Lactose (R) 1,4'-glycosidic bond
(D) Cellulose (S) Hydrolysis product is glucose
POLYMERS
(A) High density polythene is a linear polymer.
(B) Low density polythene is a branched chain polymer.
(C) Chain growth polymers are also known as addition polymer.
(D) Step growth polymer is also known condensation polymer.

(A) Elastomers have the weakest intermolecular forces.
(B) Buna-N is an elastomer with crosslinks.
(C) Some fibres have crystalline nature.
(D) Thermoplastic polymers have stronger intermolecular forces than fibres
Q.17 Match the column.
Column I Column II
(A) (CH 2  C  CH  CH 2 
)n (P) Thermoplastic polymer
|
Cl
H H O O
| | || ||
(B) ( N  (CH 2 )6  N  C  (CH 2 ) 4  C)n (Q) Thermosetting polymers
Cl
|
(C) (CH 2  CH ) n (R) Fibres
OH OH
(D) (S) Elastomer

Column I Column II
(A) Teflone (P) Natural Polymer
(B) Natural Rubber (Q) Condensation
(C) Terylene (R) Linear Polymer
(D) Proteins (S) Co-Polymer
POC
CHO
Q.19 AcONa (P)
+ AC2O
Before isolating (P) unreacted Ph–CHO is removed first. Select the correct statement.
(A) P is cinnamaldehyde
(B) Removal of PhCHO is done by passing steam into the mixture
(C) Removal is done by simple distillation
(D) P is cinnamic acid.
Q.20 Match the column
Column I Column II
(component of mixture) (Reagent)
(A) Crystalline Na2CO3 + Sodium citrate + CuSO4(aq. sol.) (P) Fehling solution
(B) CuSO4 + Rochelle Salt + NaOH(aq. sol.) (Q) Nesseler's Reagent
(C) 10%  - naphthol in alcohol (R) Benedict's solution
(D) HgCl + KI + KOH (aq. sol.) (S) Molisch's Reagent
EXERCISE III
Q.1 The pKa values for the three acidic group P,Q,R are 4.3, 9.7 and 2.2 respectively
(R) (P)
HOOC–CH –CH2–COOH
+
NH3
(Q)
Calculate the isoelectric point of the amino acid ?
Q.2 Statement 1 : Bromine water changes glucose to gluconic acid.

Statement 2 : Bromine water acts as oxidising agent.
(A) Statement-1 is true, statement-2 is true and statement-2 is correct explanation for statement-1.
(B) Statement-1 is true, statement-2 is true and statement-2 is NOT the correct explanation for statement-1.
(C) Statement-1 is true, statement-2 is false.
(D) Statement-1 is false, statement-2 is true.
Comprehension (3 to 5)
Consider the following reversible process for a reaction of D-glucose.
+
H
Y
CH2OH O -D-isomer
HO H  CH 3OH
OH  [X]
OH
HO
D-glucose Z
( or  form) + -D-isomer
H
Q.3 The structure of intermediate [X] is

 CH2OH O
CH2OH O
HO OH
(A) (B) OH
OH
HO O
CH 2OH O CH2OH O
HO HO
(C) (D) OH
O OH
HO HO
Q.4 Select the correct option.

CH2OH O CH2OH O
HO HO
(A) Y is H (B) Z is OCH3
OH OH
HO OMe HO H
CH2OH O
CH2OH O HO
H
(C) Y is OH (D) Z is OH
OH HO OCH3
H
OCH3
Q.5 Which of the following is positional isomer of -D glucose?
CH2OH O
CH2OH O
HO
(A) OH (B) HO OCH3
HO OH
OCH3 HO
OH OH
CH2OH CH2OH
(C) HO OH (D) HO OCH3

OH OH
O O
Comprehension (Q.6 to Q.8)
G
The monomer (G = Me or Cl) when treated with Zieglar - Natta catalyst undergo polymerisation
in the manner given below -
Zieglar-Natta
n
Catalyst n
cis-poly-1,3-butadiene
Q.6 The Zieglar-Natta catalyst is
(A) TiCl4 (B) R3Al (C) R3 Al / TiCl4 (D) R3 B/TiCl4
Cl
Q.7 The polymer obtained when monomeric unit used is CH2=C–CH=CH2
(A) Neoprene (B) Stilbene (C) Styrene (D) Chloropicrin
Q.8 Which of the following statement is not true considering the process given above.
(A) The general class of polymer formed is known as homopolymer
(B) The polymer obtained is stereoregular
(C) Buna–N can be prepared using above process
(D) Synthetic rubber can be formed by above process using 1,3- butadiene.

Column I Column II
(Carbohydrate) (Properties)
(A) Starch (P) Mutarotation

(B) Sucrose (Q) Non reducing sugar
(C) Lactose (R) -glycosidic bond
(D) Maltose (S) -glycosidic bond
(T) Reducing sugar
(U) Hemiacetal

Column I Column II
CH2OH O
HO H
CH2OH O
(A) HO OH O OH (P) -glycoside bonds
OH
HO H
H OH
O H
CH 2 O OH
HO
(B) OH O (Q) Reducing sugar
OH OH
HO HOCH2
CH2OH O H
HO
HO
HO
O
HOCH 2 O
(C) (R) Forms enediol intermediate
HO
CH2OH
OH
HOCH2 HOCH2
O O
(D) HO O OH (S) -glycoside bond
HO OH HO OH

Column I Column II
(A) Addition polymer (P) Buna-S
(B) Condensation polymer (Q) Buna-N
(C) Homopolymer (R) Polythene
(D) Copolymers (S) Nylon 6,6
Q.12 Match the column
Column I Column II
(Functional group) (Test used or complex formed during confirmatory test)
(A) Aldehydic (P) [(C6H5O)6Fe]–3 (violet)
–
CH — C–O
O O
Cu
(B) Phenolic (Q) O (blue)
O
–
CH — C–O
RCH(OH)OSONH
(C) Alcohol (R) C NH
RCH(OH)OSONH violet red
(S) (ROH)2Ce(NO3)4 (Red)
(T) Molisch's Test
Q.13 Read following statements.

(a) Protein on complete hydrolysis give.
(b) Hormons belong to the class of
(c) Carbohydrates are stored in the body as
(d) The excess of glucose is stored in the liver as
Which set of terms correctly identifies the statements given above.
(i) Lipids (ii) -amino acid (iii) Peptides (iv) Fats
(v) Proteins (vi) Cellulose (vii) Glycogen (viii) Peptones
EXERCISE-I
Q.1 D Q.2 A Q.3 D Q.4 B Q.5 A Q.6 A Q.7 B
Q.8 B Q.9 A Q.10 C Q.11 A Q.12 D Q.13 C Q.14 A
Q.15 D Q.16 B Q.17 A Q.18 A Q.19 C Q.20 A Q.21 D
Q.22 C Q.23 B Q.24 D Q.25 A Q.26 C Q.27 A Q.28 A
Q.29 C Q.30 A Q.31 A Q.32 B Q.33 B Q.34 D Q.35 C
Q.36 C Q.37 B Q.38 B Q.39 A Q.40 B Q.41 B Q.42 B
Q.43 B Q.44 B Q.45 D Q.46 B Q.47 C Q.48 A Q.49 A
Q.50 D Q.51 C Q.52 B Q.53 D Q.54 C Q.55 B Q.56 C
Q.57 D Q.58 C Q.59 B Q.60 B
EXERCISE II
Q.1 A,B,C,D Q.2 A,B,C,D Q.3 A,B,C Q.4 B,D Q.5 B,C,D
Q.6 A,B,D Q.7 A,B,C Q.8 B,C,D Q.9 A,B,D Q.10 A,B,C,D
Q.11 A,B,C Q.12 B,C Q.13 A,B,C,D Q.14 (A) Q,S (B) S (C) R,S (D) R,S
Q.15 A,B,C,D Q.16 A,B,C Q.17 (A) S, (B)R, (C)P, (D) Q
Q.18 (A) R (B) P,R (C) Q,S (D) P,Q,S Q.19 B,D Q.20 (A)R (B) P (C) S (D) Q
EXERCISE III
Q.1 3.25 Q.2 A Q.3 A Q.4 D Q.5 C Q.6 C Q.7 A
Q.8 C Q.9 (A) Q,S (B) Q,S (C) P,R,T,U (D) P,S,T,U
Q.10 (A) P,Q,R (B) P (C) P (D) P,Q,R Q.11 (A) P,Q,R (B) S, (C) R, (D) P,Q,S
Q.12 (A) Q,P (B) P, (C) S (D) T Q.13 2577

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GENERAL ORGANIC CHEMISTRY FINAL LAP - 2019

RESONANCE & AROMATICITY

Q.1 Which of the following statements is (are) true about resonance.

Q.2 Consider structural formulas A, B and C:

(A) (B) (C)

Q.4 Which of the following statement is incorrect ?

Q.6 In which of the following lone-pair indicated is involved in resonance :

(a) (b) (c) (d)

Q.7 In which of the following lone-pair indicated is not involved in resonance :

(d) (e) O¯ (f) + NH (g)

Q.10 Write stability order of following intermediates:

(ii) (a) + (b) + (c) +

Q.11 Write stability order of following intermediates:

(i) (a) C6H5+ (b) p–NO2(C6H4)+ (c) p–CH3–(C6H4)+ (d) p–Cl–C6H4+

(ii) (a) (b) (c)

CH2 CH2 CH2

Q.13 Write stability order of following intermediates:

(ii) (a) (b) (c)

(iii) (a) (b) (c)

(v) (a) (b) (c)

Q.16 C1 – C2 bond is shortest in

(A) (B) (C) (D)

Q.17 In which of the following resonance is possible

Q.18 Which of the following compounds have delocalised electrons ?

(C) CH3CH2NH CH2 CH = CH2 (D) CH2 = CH – CH2 – CH = CH2

Q.19 Compare the C–N bond-length in the following species:

(i) (ii) (iii)

Q.20 Which of the following species are conjugated ?

(C) CH 2 = C = CH – NH 2 (D) All of these

Q.23 Discuss the following observations:

Q.24 A canonical structure will be more stable if

Q.25 Resonance energy will be more if

Q.26 In each set of species select the aromatic species.

Select the correct statement about product A.

Q.29 Which of the following is incorrectly orderd for resonance stability

(C) (I > II)

(A)  (B)

(C)  (D) 

Q.31 Hyperconjugation is possible in

(A) (B) (C) (D)

(A) (B) (C) (D)

Q.34 Explain why which compound is aromatic, antiaromatic or nonaromatic.

Q.36 Which one of following represents different molecules?

(A) and (B) and

(C) and (D) and

(i) (a) (b)

(ii) (a) (b) (c) (d)

(c) (I) and (II)

(d) (I) CH 3  CH  CH 3 and (II) CH 3  N  CH 3

(i) (a) (b) (c)

(ii) (a) (b)

(iv) (a) (b) (c) (d)

Q.43 Select the correct statement.

Q.44 Arrange following compounds in decreasing order of electrophilic substitution.

(i) (ii) (iii) (iv)

Q.46 In which of the following pairs, indicated bond is of greater strength :

(a) and CH 2  CH 2 (b) CH3  C  CH and HC  CH

Q.48 Match each alkene with the appropriate heat of combustion:

Q.50 Compare heat of hydrogenation (Decreasing order)