Alcohol, Phenol and Ether

FINAL TOUCH
REVISION
OF
ORGANIC CHEMISTRY
FOR JEE ADVANCED
BY
NAVNEET JETHWANI
ALCOHOL, PHENOL
&
ETHER
ETOOSINDIA
INDIA’S NO. 1 ONLINE COACHING
Plot No. 38, Near Union Bank of India, Rajeev Gandhi Nagar,
Kota, Rajasthan – 324005 Mob. : 9214233303
ETOOSINDIA F.T.R. BY N.J. SIR
Single Choice Question Exercise

1. Identify the major product.
H 2SO4
  Pr oduct
(A) (B) (C) (D)
Ans. (A)
2. Predict the product when given compound reacts with LiAlH4 :
O O
C C
H OCH3
(A)
O
O
C O CH3
C O CH3
(A) (B)
O
C
H
(C) (D)
Ans. (C)
18
CO2H CH2 
H
3. + 18 

(A) ; Product (A) is :
CO2H CH2
O O
18
C O CH2 C O CH2
(A) (B) 18
C O CH2 C O CH2
O O
Plot No. 38, Near Union Bank of India, Rajeev Gandhi Nagar, Page # 2
18
O
O O
C O CH2
(C) (D) H O C C O CH2 CH2
C O CH2
18
O
Ans. (B)
O O NaBH4
4.  (P)
O
O 
LiAlH
 (Q)
4
Sum of number of 1° alcoholic groups in product (P) and (Q) is :

(A) 1 (B) 2 (C) 3 (D) 4
Ans. (D)
O LiAlH
4
(A)
5. xAc2O
O
(B)
x = moles of anhydride consumed

(A) 1 (B) 2 (C) 3 (d) 4
Ans. (C)
6. For the following reaction, select the statement that best describes the change.
RCH2OH + PCC [C5H5NH+ClCrO3–] 
(A) The alcohol is oxidized to an acid, and the Cr(VI) is reduced
(B) The alcohol is oxidized to an aldehyde, and the Cr(VI) is reduced
(C) The alcohol is reduced to an aldehyde, and the Cr(III) is oxidized
(D) The alcohol is oxidized to a ketone, and the Cr(VI) is reduced
Ans. (B)
7. Two unknown compounds X and Y, both having molecular formula C4H8O, give following results with four
chemical tests.
Bromine Na metal Chro mic acid

Compound X decolou ris es b ubbles Orange to Green
Compound Y No reaction No reactio n No reaction
Compound X and Y respectively are :

O
(A) CH3 CH2 C CH3 ; (B) OH ;
O O
O
(C) ; (D) CH3 CH2 CH2 C H;
OH
O O
Ans. (B)
8. Give the major organic product of the following reaction.
O
(1)sodium acetylide

(2)H O,H  to neutralize
 Product
2
O OH HO
(A) (B) (C) (D)
Ans. (C)
OH OH
 (A) OH +OH
PCC (1)MeMgBr NaBH 4 ,EtOH
9.  (B) 
(2)H O 
(C)  (D)
H 3
Product (D) in above reaction is :
OH OH OH OH OH OH
OH
(A) (B) (C) (D)
OH
Ans. (B)
PBr3 Mg, ether

(A) (C) Grignard reagent

H 3O
10. Na2Cr2O7 
(D)   (3, 4-dimethyl 3-hexanol)
(B)
H2SO4
When Grignard reagent reacts with (B) product (D) will obtained. Reactant (A) of the above reaction is :
OH
(A) (B) OH (C) (D)
OH OH
Ans. (A)
11. Ph CH2 CH K
CH3  C2 H5 Br
  (A)
OH
Product (A) in above reaction is :
(A) Ph CH2 CH CH3 , (inversion) (B) Ph CH2 CH CH3 , (retention)
OEt OEt
(C) Ph CH2 CH CH3 , (racemic) (D) Ph – CH = CH – CH3
OEt
Ans. (B)
O O
CH3 CO C OCH3 (i)LiAlH4
12. 
(ii)H2 O
 (A) ; Product (A) of the reaction is
(96%)
OH OH OH CH2 OH OH CH2OH O
(A) (B) (C) (D)
Ans. (C)
13. What is the major organic product of the following sequence of reactions ?
O
(CH3)2CHCH2OH  H2C CH2 

?
PBr3 Mg H3 O
  
OH OH
(A) (CH3)2CHCHCH 2CH 3 (B) (CH3)2CHCH2CH2OH (C) (CH3)2CHCH2CHCH3 (D) (CH3)2CHCH2CH2CH2OH
Ans. (D)
O CH2 OH
14. CH2 OH LiAlH 4 H 3O

(C) . Product C is :

CH CO2Et +
(A)  (B) 
H
CH3
O O
(A) (B)
CH2 CH OH CH CH2 OH
CH3 CH3
O O
(C) OH (D)
C CH3 CH2 CH2 OH
CH3
Ans. (B)
O
O
O O
O O O O
15. 
(A)

(B)

(C)

(D)
CO2CH3
CO2CH3 CHO
CH2 OH CHO
Identify correct combination :
CH2 OH
(A) (A)= (B) B = NaBH4 (C) (C) = KMnO4 (D) (D) = H3O
CH2 SH
Ans. (D)
16. What is true for the equilibrium reaction ?
O O
CH3 C OH + CH3 
OH 
cat.
 CH3 C O CH3 + H2O
(A) The use of equimolar quantities of CH3OH and CH3COOH will give the greatest yield of the ester at
equilibrium.
(B) Removal of water will increase the amount of ester at equilibrium.
(C) Addition of CH3COOCH3 will cause the formation of an equal number of moles of water.
(D) Application of pressure increases the amount of ester at equilibrium
Ans. (B)
O
OH
Pbr3 Mg (1) V CH3 C Cl
W X (2) H O+ Y Z
17. ether 3
Na2Cr 2O7
V
Product Z of above reaction is :
O
O
O C CH3
O C CH3
(A) (B)
O O
O C CH3 O C CH3
(C) (D)
Ans. (B)
18. Find out the reaction in which obtained product give positive isocyanide test :
O O
(A) LiAlH4 (B) NaBH 4
NH2  NH2  
NH LiAlH4
NH NaBH 4
(C)   (D)  
O O
Ans. (A)
O OH
O O
19. H
O O
In the above given compound how many functional group reduced by LAH (Lithium aluminium hydride) and
SBH (sodium borohydride) respectively ?
(1) 4, 4 (2) 4, 2 (3) 3, 4 (4) 4, 2
Ans. (B)
20. Correct order of dehydration of following alcohols will be :
OH OH OH OH
1 2 3 4
(A) 1 < 2 < 3 < 4 (B) 4 > 3 > 1 > 2 (C) 4 > 2 > 1 > 3 (D)1 > 3 > 4 > 2
Ans. (C)
OH OH
Et Me
+
21. H ? product is :
Et Me
(A) (B)
Me O O Et
Et Me
(C) (D)
Ans. (D)
Mg Hg Conc. H2SO4
Q.22 2Ph C CH3 Product
H 2O 
O
The main products is :
(A) Ph C C Ph (B) CH 3 C C CH 3
O O O O
Ph Ph
(C) Ph C C CH3 (D) Ph C C CH3
O O
CH3 CH3
Ans. (C)
CH3 CH3
Q.23 H3C C CH CH2 H3C C CH CH3 , This interconversion can be achieved by :
CH3 CH3 OH
(A) Acid catalysed hydration (B) Oxymercuration-demercuration

(C) Hydroboration - oxidation (D) Any method mentioned above
Ans. (B)
24. Which of the following ethers is the most unreactive to eleavage with conc. HBr ?
(A) Ph–CH2–O–CH3 (B) Ph–O–Ph
O O
(C) (D)
Ans. (B)
25. Consider the reaction of HI with the following :
(I) (II)
O
which forms di-iodide on reaction with HI (excess)?

(A) I and II both (B) II only (C) I only (D) none
Ans. (C)
Br
Mg (i) 14CO2 NaHCO3
26 (A) (B) (C) gas, product C is :
(ii) H+/H2O
(A) CO (B) 14CO2 (C) CO2 (D) A mixture 14CO2 and CO2
Ans. (C)
27. SOCl2 Mg. O

OH 
Product
Pyridine Et2O
O H 3O
Product of reaction is :
O
OH CH3
(A) (B) CH C
O CH3
O
CH3 OH
(C) (D)
O CH2 C CH2 OH CH2 CH2 C CH3
O
CH3 CH3
Ans. (D)
O
O
Br2/h Mg. 1. Conc.H2SO4 O3
28. A B C D E
Et2O 2. H3O
+ Zn/H2O
Find out the structure of ‘A’ :
CH3
(A) (B) (C) (D)
Ans. (C)
COOH MgBr
29. + X+Y
(1 eq.)
SO3H
X and Y are respectively :
COOH MgBr
(A) only (B) and
SO3H
COOH
(C) and (D) None of these
SO3MgBr

Ans. (C)
O
PhMgBr (excess)
30. Cl C Cl (X) ; Product (X) is :
H 3O +
O O O
OH
O
(A) Ph C Cl (B) Ph C Ph (C) Ph C Ph (D) Ph C Ph
Ph
Ans. (C)
SH
SH
OC2H5 (1) 'X' CH3MgBr
31. HO
HO
O HO
(A) 2 (B) 3 (C) 4 (D) 5

Ans. (C)
MgBr THF+ (X)

+ BrMg H3O
32.
O
Identify (X) :
(A) (B)
OH
OH O
HO
OH
(C) (D)
HO O OH
Ans. (A)
33. Predict the reducing agents in following reaction.
H
O ?
OH
(A) LiAlH4 (B) NaBH4 (C) H2 / Pt,  (D) Both (A) and (B)
Ans. (C)
34. Predict major organic product from the following reaction:
H3C O NaBH4
A
LiAlH4
B
O
OH OH O OH
OH OH O OH
(A) A B (B) A B
O OH OH OH
OH OH O
OH
OH O
O OH
(C) A B (D) B
A
OH OH OH
O
Ans. (B)
35. In the given reaction
H3C (i) Hg(OAc)2/CH3OH

C CH CH3 [X] , [X] will be :
(ii) NaBH4, OH
H3C
OMe OMe
H3C C CH2 CH3 CH3
(A) (B) H3C CH CH
CH3
CH3
(C) H3C CH CH2 CH3 (D) H3C CH CH2 CH3

CH3 CH3
Ans. (A)
36. Find out correct product of reaction :
HBr
(Excess)
Br
(A) (B)
O OH Br
(C) (D)
Br Br Br OH
Ans. (B)
37. , S is :
OH
OH
OH
(A) (B) (C) (D) OH
Ans. (B)
38.
Find out ‘A’ of the reaction
HO OH HO CH2 OH
(A) (B)
HO CH2 OH
(C) (D)
Ans. (C)
39. ; Products of the reaction are :
(A) Racemic mixture (B) Diastereomers (C) Meso (D) Optically pure
Ans. (B)
40. The conversion
O OH
H3C C CH2 CH2CO2CH3 H3C CH CH2 CH2 CH2OH
Can be effected using :

(A) LiAlH4 and then H+ (B) B2H6(THF) (C) H2 / Ni (excess) (D) All
Ans. (D)
H3O+ HBr Mg / ether HCHO HI E;

41. CH3MgBr + A B C D
H3O+
Product E is
(A) (B)
I
CH3 CH2I CH2CH3
(C) (D)
I
I
CH3 CH3
Ans. (D)
H2O dil. H2SO4 H2
42. In the reaction sequence , CaC2 A B Ni C , true about the product C is
Hg+2
(A) Give yellow ppt, with NaOI

(B) Its final oxidation product is carbonyl compound
(C) Its final oxidation product is CO2 and H2O
(D) Its final oxidation product is CH3COOH with Cu(300°C)
Ans. (A)
CH3CH2OH
43. CH CH 2 H2SO4
CH2CH3
(A) (B) CH2 CH3
OCH2 CH3
OCH2 CH3
CH2CH3
(C) (D) CH CH3

OCH2 CH3
OCH2CH3
Ans. (A)
H2O/H
44. 'X' ; Product ‘X’ will be
O O
CH3
(A) (B)
(C) (D) All of these
Ans. (A)
SOCl 2 Mg. O
45. Product
Pyridine, Et 2O H

O CH2OH
The final product is :
(A) (B)
(C) (D)
Ans. (B)
46. Select the major product of following reaction :
CH 3CH 2O
Cl
O O
(A) (B)
OCH2CH3
OCH2CH3
(C) O (D)
Cl
Ans. (D)
47. Identify the final product of following sequence of reactions :
TsCl alc. KOH OsO4 HIO4

OH
Pyridine
(A) (B) H
O
(C) (D) OH
OH
Ans. (B)
48. The product of the reaction is :
O
1. KH
HS 2. H 2O
OH S O
S
(A) (B)
OH
(C) HS–(CH2)5–O–Et (D) HS (CH2)4 CH

OH
Ans. (A)
49. Identify the major product of reaction :
OH
TSCl KSH
Pyridine
D
H
SH SH
(A) (B)
D D H
H
D
(C) (D) No reaction
H
Ans. (B)
50. Final product is ?
CH3 CH3
(A) (B) C C
H H
(C) (D)
Ans. (C)
18
O +
H3O
51. ; Major organic product
18 18 18
OH OH OH OH
18 18
O O O
(A) (B) (C) (D)
Ans. (D)
52. Phenol and ethanol are distinguished by the reaction with
(A) Red litmus (B) NaHCO3 (C) FeCl3 (D) Na
Ans. (C)
53. Which of the following reactions would give the best yield of t-butyl methyl ether ?
H 2SO4
(A) (CH3)3C –OH 
140 C
 (B) (CH3)3C–Br + CH3OH 
 
(C) (CH3)3C–Br + CH3O Na (D) (CH3)3C – OK + CH3Br 
Ans. (D)
CH CH2
CH2CH3 C
OH
54. B A
CH2CH2 OH
CHCH3
OH
Select schemes A, B, C out of

(I) Acid catalysed hydration (II) HBO (III) Oxymercuration-demercuration
(A) I in all cases (B) I, II, III (C) II, III, I (D) III, I, II
Ans. (C)
CH3
TsCl KSH
H OH  (A)   Products
55.
Et
(1 mole)
(Assuming all the substrate convert into substitution products containing 0.05 mole of S-configuration) Calculate
the percentage of SN2 mechanism.
(A) 90% (B) 80% (C) 70% (D) 95%
Ans. (A)
(i )CH 3CN (i )RMgX
56. RMgX 
(ii )H 2 O
(A) 
(ii)H 2O
(B) , (B) will be
(A) 1° ROH (B) 2° ROH (C) 3° ROH (D) Alkene

Ans. (C)
57. The major products of following reaction sequence are :
OH OH
Ph H 2SO 4  I 
LiAlH 4 H
Ph  (1) (2)
 II 
(3)
III
O O
Ph
Ph
(A) I = Ph (B) I = Ph
Ph Ph
Ph Ph
(C) III = (D) III =
Ans. (B)

H /
58. 
Catalyst Product
OH
(A) (B) (C) (D)

O OH HO
HO
Ans. (C)
CH3
HI(cold)
O  A  B
59. conc.
A, B are
CH3
OH
OH
CH3
(A) H (B) C2H5I (C) CH3I (D)
H
(R)
(S)
Ans. (B)
60. The end product of following reaction is :
Me
Na Me-I
Dry Ether
(A)
H OH Ether
SOCl2 NaOMe (B)
Low Temp.
Et
Identify relationship between products ?

(A) Diastereo Isomers (B) Enantiomers
(C) Functional Isomers (D) Geometrical Isomers
Ans. (B)
61. Which of the following is/are the proper sequence of reagents for the conversion
OH Ph
OH
OH
O
||
(A) 
PBr3 Mg/Et 2O
  Ph  C  H
  H2SO4
  OsO4
  
 H 2O
PCl3 PhMgBr Br2 alc.KOH PhCO3H

(B)         
H O 3 H O 3
O
||
(C)  CH3MgBr
  H 2SO 4
  Ph  C  H
OsO4 alkaline
  
H O  3
KMnO4 PhMgBr H2SO4 Cold alkaline

(D)  
H O
 
 
KMnO4 solution
3
Ans. (D)
62. Acetone (CH3COCH3) is the major product in :


H3O
I. CH2 = C = CH2   H 2SO4 /HgSO4
II. CH3C  CH  
BH3 .THF
III. CH3C  CH 
H 2O2 /OH
(A) I, II (B) I, III (C) II, III (D) I, II, III

Ans. (A)
Multiple Choice Exercise

1. Which combination of reagents will not bring about the following conversion ?
Br
(A) MeMgBr/H  , H 2SO 4/ , HBr/H 2O 2,h  (B) MeMgBr/H  , H2SO 4/ , HBr
(C) MeMgBr/H  , HBr/CCl4 (D) HBr/H 2O2, MeMgBr/H 
Ans. (B,C,D)
2. Which of the following reactions proceeds with inversion of configuration ?
Me Me
Na CH3Br TsCl CH3ONa
(A) H OH (B) H OH
Et Et
Me Ph
PCl5 CH3ONa SOCl2 KCN
(C) H OH (D) H OH
Et CH3
Ans. (B, D)
3. Products obtained in the following reaction.
(i) CH3MgCl
O
(ii) NH4Cl
OH
(A) (B)
OH
(C) OH (D)
OH
Ans. (A, B, D)
4. Which of the following are correct regarding the products of the given reaction
Me
Me
H CN aqueous acetone
H H
H
Cl
OCH3
Me Me Me
Me Me H Me
H H
CN OH CN HO CN
H H H H H H
H H
OH H H
OCH3 OCH3 OCH3

(X) (Y) (Z)
(A) only X and Z are formed (B) Y > Z (amount) (C) X > Y (amount) (D) Y > X (amount)
Ans. (B, D)
H H
TsCl NaBr
5.   X  Y. X and Y are :
Pyridine
CH3 OH
H H H Br H
H H
(A) X = (B) Y = (C) X = (D) Y =
||
CH3 OTs CH3 H OTs

CH3 Br
Ans. (A, B)
6. What are the possible intermediates of the following reaction which form during this reaction path way ?
H3PO4
 
Δ
(A) (B) (C) (D)
Ans. (A, B, D)
7. Which of the following reaction are not feasible ?


(A) O N a + CH3Br  OCH3
(B) + RO– 
CH3 CH3
(C) CH3 Br + ROH  CH3 OR
CH3 CH3
 
(D) Br + RO N a  OR
Ans. (B, D)
8. What are the products expected in the following reactions ?
O O
CH2N 2
C6H5 – C – CH2– C – CH3
Ether
OCH 3 O O OCH3
(A) C 6H5 C = CH – C – CH 3 (B) C6H5 C – CH = C – CH3
OCH3 O O OCH3
(C) C6H5– C – CH – C – CH3 (D) C6H5– C – CH – C – CH3
CH2 CH2
Ans. (A, B)
9. The intermediate stages in the conversion
(CH3)2– C – C – (CH3 )2 CH3COC (CH3)3 are
OH OH
(A) (B)
(C) (D)
Ans. (A, B, C, D)
OH
25°C (A)
Conc. Conc. H2SO4
10. H2SO4
at 100°C
100°C (B)
The compounds given are :
OH
SO3H
SO3H
(II)
(I)
Which of the following statements is/are correct ?

(A) Compounds (A) and (B) are (I) and (II), respectively.
(B) Compound (I) is the major product at lower temperature when the reaction is under kinetic or rate control.
(C) Compound (II) is the major product at high temperature when the reaction is under thermodynamically or
equilibrium control.
(D) Compound (II) is more stable.
Ans. (A, B, C, D)
11. Which of the following statements is/are correct ?
(A) 4-Chlorophenol (I) will dissolve in NaOH but 4-chloro-1-methyl benzene (II) will not.
(B) 4-Methyl benzoic (III) acid will dissolve in aq. NaHCO3 but 4-methyl phenol (IV) will not.
(C) 2, 4, 6-Trinitrophenol (V) will dissolve in aq. NaHCO3 but 4-methyl phenol (VI) will not.
(D) 4-Ethyl phenol (VII) will dissolve in aq. NaOH but ethyl phenyl ether (VII) will not.
Ans. (A, B, C, D)
12. Which of the following paths is/are feasible for the preparation of ether (A) ?
Me
(A) Path I: Ph + EtONa
Br
Me
(B) Path II: Ph + EtBr
Me
ONa
Ph
1. Hg(OCOCF3)2
OEt
(C) Path III: Ph + EtOH
2. NaBH4 (A)
1. Hg(OCOCF3)2
Me
(D) Path IV : Ph + EtOH
2. NaBH4
Ans. (B, C)
13. Which of the following statements is/are correct about the following reactions ?
Cl OH
NO2 NO2
1. NaOH HNO3
Path (I)
2. H3O
 H2SO4
OH
NO2 NO2 O2N NO2
(A) (B)
Path (II) NO2

Cl (C)
O2N NO2
HNO3 1. NaOH
H2SO4 2. H3O

NO2
(A) Path I is feasible.

(B) Path II is feasible.
(C) PhCl cannot be trinitrated because Cl and two NO2 atoms deactivate the ring towards further SE reaction.
(D) 2,4-dinitrophenol can be nitrated because the two deactivating NO2 groups prevent ring oxidation.
Ans. (A, C, D)
14. Which of the following statements is/are correct ?
(A) The nitration of phenol is faster than phenyl acetate.
(B) The reaction of PhO– is faster than NC O with PhCH2Cl.
(C) Base-catalysed hydrolysis of p-nitrophenyl acetate is faster than phenyl acetate.

(D) Acid-catalysed esterification of PhOH is faster than p-nitrophenol with MeCOOH.
Ans. (A, B, C, D)
15. Phenol can be prepared by
(A) Hydrolysis of chlorobenzene with aqueous KOH solution.
(B) Heating sodium salicylate with (NaOH + CaO).
(C) Reacting cumene hydroperoxide with dil. H2SO4.
(D) Heating benzenediazonium chloride with dil. H2SO4.
Ans. (B, C, D)
Hot HI Alc. KOH/

16. A(C5H10O) C5H10I2(B)
(Chiral ether)
2 4
1
5
3
(C)
(1, 3-Pentadiene)
The structure of (A) is :
O O
Me O
(A) (B) (C) (D)
O Me
Me Me
Et
Ans. (A)
17. What is the major product of the following reaction ?
NaBH 4
  product
CO2H
OH OH
O OH
(A) (B) (C) (D)
CO2H CH2OH CO2CH3

CO2H
Ans. (A, B)
Misc. Exercise
Subjective Questions
PCl5 +
KCN H 3O NH3 heat
1. C2H5OH   (A)   (B)    (C)   (D)   (E)
PBr5 KOH(Alc.) HBr NH3
2. CH3CH2CH2OH   (A)   (B)   (C)   (D)
3. Provide products in the following reactions :
SOCl2 Hg(OAc) 2 NaBH 4

(a) OH   (b)   
Pyridine CH 3OH
(c) mCPBA
 
4. Complete the following reactions
CH3MgBr
(a)  +
 A
H3O
O
H3C
CH3MgBr
(b) CH2CH2CH3  +
 A
H3O
H3C O
mCPBA C2 H 5MgBr
(c) CH3CH=CH2   A  +
B
H 3O
5. Compound (A) C4H10O reacts rapidly with metallic sodium, but undergoes almost no reaction with Lucas reagent.
When (A) is treated with hot concentrated sulphuric acid, a new compound (B) C4H8 is formed. If C4H8 is hydrated
with sulphuric acid a new compound (C) C4H9OH is formed, which is almost inert to metallic sodium but reacts
rapidly with Lucas reagent. What are (A), (B) and (C) ?
6. A compound (X) containing C, H and O is unreactive towards sodium. It does not add bromine. It does also not
react with Schiffs reagent. On refluxing with an excess of HI, (X) give only (Y). (Y) on hydrolysis gives (Z) which
can be converted to (Y) by the action of P + I2. Compound (Z) on oxidation gives an acid of equivalent weight 60.
What are (X), (Y) and (Z) ?
7. An alkyl iodide (A) C3H7I when treated with an aqueous solution of an alkali, (B) is formed. (B) on oxidation
produced only one compound (C). C3H7MgBr when treated with (C) gives (D) C6H14O which reacts rapidly with
Lucas reagent. Identify (A) to (D).
8. Compound (A) reacts with sodium to liberate H2, forming a compound (B). When (A) it treated with HCl + ZnCl2,
an immediate reaction takes place liberating (C). When (A) is heated with H2SO4, (D) is formed. Ozonolysis of (D)
gives a 3 carbon aldehyde and 3 carbon ketone. What are (A), (B), (C) and (D) ?
9. An organic compound (A) C4H10O reacts with HI giving a compound (B) C4H9I, which on reduction gives a
normal hydrocarbon having four carbon atoms. On oxidation (A) gives (C) C4H8O and then acid (D) C4H8O2.
What are (A) to (D) ?
10. An organic compound (A) C3H8O on treatment with excess of hot conc. H2SO4 gives a compound (B). (B) on
treatment with HBr gives (C) which on hydrolysis yields (A). (C) when dissolved in ether and treated with
sodium gives (D). What are (A) to (D) ?
11. An alcohol (A) on treatment with conc. H2SO4 gave an alkene (B). The compound (B) on reacting with Br2 water
and subsequent dehydrobromination with NaNH2 produced a compound (C). The compound (C) with dil. H2SO4
in presence of HgSO4 gave a compound (D). The compound (D) can also be obtained by oxidation of (A) by
KMnO4 or from dry distillation of Calcium acetate. Name (A), (B), (C) and (D) explain reactions.
Comprehension
Paragraph - 1 (12 to 14)
Alcohols are converted to tosylates by treatment with p-toluene sulfonyl chloride (TsCl) in presence of pyridine.
This overall process converts a poor leaving group (OH) into better one (OTs) . A tosylate is a better leaving
group because its conjugated acid p-toluene sulfonic acid is strong acid.
Because alkyl tosylates have better leaving tendency they undergo both nucleophilic substitution and -
elimination.
O
Pyridine
CH3CH2 OH + Cl S CH3 
O
poor leaving Tosyl chloride
group (TsCl)
O
CH3CH2 O S CH3 + + Cl
+
O N
H
or
CH3CH2 OTs Better leaving group

2
 SN 
NaOCH3+ CH3CH2 OTs CH3CH2 OCH3 + NaOTs
 E2 
KOH + H CH2 CH2 OTs H 2C CH2 + KOTs
(Alcoholic)
12. Find the major product of following reaction :
H3C H
H C
(A) C CN (B) CH3 CH
CH3 CH2 CH3
CH3 H
H H3C C CH2CH3
(C) NC C (D)
CH2CH3 NC
13. What would be the major product of following reactions ?

Pyridine CH3CH 2ONa
OH + Ts Cl
(A) (B) OCH2CH3
OTs
(C) (D) O CH CH2
14. Identify the final product of following sequence of reactions :
OH TsCl alc. KOH OsO4 HIO4

Pyridine
(A) (B) H
O
(C) (D) OH
OH

Symmetrically substituted epoxides give the same products in both the acid catalysed and base catalyzed ring
opening. An unsymmetrical epoxide gives different products under acid catalysed and base catalysed conditions.
Under basic conditions, the alkoxide ion simply attacks the less hindered carbon atom in an SN2 displacement.
Under acidic conditions, the alcohol, attacks the protonated epoxide.
H H H
O O O
+ +
CH2 – C – CH3 CH2– C – CH3 CH2– C – CH3
CH3 CH3 CH3
(I) (II) (III)
Structure II and III show that the oxirane carbon share part of positive charge. The tertiary carbon bear a larger part
of positive charge and it is more strongly electrophilic. The bond between tertiary carbon and oxygen is weaker
implying a lower transition state energy for attack at the tertiary carbon. Attack by the weak nucleophilic is sensitive
to the strength of electrophilic is sensitive to the strength of electrophile. Centre attack takes place at more electrophilic
carbon which is usually the more substituted carbon because it can better support the positive charge.
15. What will be the products in following reactions
CH 3– CH 2ONa
O X
CH 3– CH 2OH
CH3
OH H OCH2CH3
(A) (B)
CH3 OCH2–CH3 CH3 H
H
(C) (D)
CH3 CH3
H2SO4
O Y
16. CH3– CH2–OH
CH2–CH3
C2 H5
(A) (B)
C2H5
(C) (D) None

C2H5
O18
+
H2O/H
17. CH2 CH Z
CH3
(A) CH2 CH (B) CH2 CH
CH3 CH3
(C) CH2 CH (D) None
CH3
O
CH3–ONa
18. P:
CH3–OH
OH OCH3
OH OH
(A) OCH3 (B) (C) (D)
H2SO4
19. Q:
CH3–OH
(A) (B)
(C) (D) None
Phenols are converted into their salts by aqueous NaOH but not by aqueous bicarbonates. The salts are converted
into the free phenols by aqueous mineral acids, carboxylic acid or carbonic acids. Most phenols have Ka value of
about 10–10, and are tremendously more acidic than alcohols. The difference in acidity are due to difference in
stabilities of reactants and products. Phenol and phenoxide ions contain benzene ring and therefore must be hybrid
of Kekuley structures
OH OH O O
and
Being basic, oxygen can share more than a pair of electron with the ring.
+O–H +O–H +O–H O O O
and
Phenol Phenoxide ion
Since energy must be supplied to separate opposite charge, the structure of phenols should contain more energy.
The net effect of resonance is therefore to stabilise the phenoxide ion to a greater extent than the phenol and thus
to shift the equilibrium towards ionization and make Ka larger than for an alcohol.
20. Which of the following is strongest acid ?
OH
(A) H2CO3 (B) (C) CH3–OH (D) CH3–CH2–OH
21. Consider the following curves :

(A) Curve A represents the ionisation of alcohol
Potential Energy
A
(B) Curve B represent the ionisation of Phenols
B
(C) Curve A represents the ionisation of phenol
(D) None
Progress of reaction
22. Which of the following is more stable:
+OH O
(A) (B) (C) Both (D) Unpredictable
23. Correct order of acidity is
OH
(A) H2CO3 > CH3–OH >
OH OH OH OH
NO2 CH3
(B) > > (C) H2CO3 > > CH3 – OH
NO2
(D) Both B and C

24. Choose the correct statement:
(A) Phenol gives effervescence with NaHCO3
(B) Picric acid is weaker acid than carbonic acid
(C) Picric acid gives effervescence with NaHCO3
O
(D) R– O is more stable than

FeCl3
A(C8H8O2) Gives intense colour
Vanillin Gives silver mirror
isolated from [Ag(NH3)2]
vanilla beans HCl
No reaction
steam
No steam distilled
(A) KMnO 4
(B) (C9H10O3)
One mole MeI
Tollens reagent C (C9H10O4)

Soluble in NaHCO3
2 Br2
(E) (F) (C7H6Br2O2) Conc. HI, 
COOH
(3, 4-Dihydroxy benzoic acid)

+ CH3I
OH
OH
25. The compound (A) is :

CHO CHO CHO CHO
OH
(A) (B) (C) (D)
OH
OH OMe OMe
OMe OH OH
26. The compound B & C are :
CHO COOH CHO COOH
OMe OMe
(A) , (B) ,
OMe OMe OMe OMe
OMe OMe
COOH CHO COOH

COOH
COOH
(C) , (D) OMe ,
OMe
COOH OMe OMe
OMe
OMe
27. The compound E & F are :-
COOH Br COOH Br
Br Br
(A) , (B) ,
OMe Br OMe OH
OH OH OMe OH
CH2OH COOH CH2OH COOH
Br Br Br
(C) , (D) ,
OMe Br OMe OH OMe
OH OH OMe OH
Match the Column

28. Match the Column I with Column II.
Column I Column II
Reaction Stereochemistry
H
(A) Me H Me  D2 /Ni
 p. Overall syn addition
(I)
MCPBA
(B) (I) 
 H 3O 
q. Optically inactive due to external compensation
Br2 /H2 O
(C) (I)   r. Optically inactive due to internal compensation
Cold alk.
(D) (I) 
KMnO4
 s. Product has two chiral centres
t. Diastereomers will be formed
29. Match the Column I with Column II.

Column I Column II
Reaction Stereochemistry
Ph Me
1. Hg(OAc)2  H 2O
(A)  
 p. Syn-hydration with anti-Markovnikov’s
2. NaBH 4 ,OH
H H
(I)
regiospecifivity
1. Hg(OCOCF3 ) 2  PhOH
(B) (I)  2. NaBH 4 q. Anti-hydration with Markovnikov’s regiospecifivity
1. B2 H6 /THF
(C) (I)  
 r. Cyclic intermediate transition state
2.H2 O2 / OH
1. B2 H 6 / THF
(D) Ph    Me 
2. CH 3COOH
 s. Overall non-stereospecific
t. Overall stereospecific

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FINAL TOUCH

Single Choice Question Exercise

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

Sum of number of 1° alcoholic groups in product (P) and (Q) is :

x = moles of anhydride consumed

Bromine Na metal Chro mic acid

Compound X and Y respectively are :

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

Product (D) in above reaction is :

PBr3 Mg, ether

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

(CH3)2CHCH2OH  H2C CH2 

14. CH2 OH LiAlH 4 H 3O

16. What is true for the equilibrium reaction ?

The main products is :

Q.23 H3C C CH CH2 H3C C CH CH3 , This interconversion can be achieved by :

(A) Acid catalysed hydration (B) Oxymercuration-demercuration

which forms di-iodide on reaction with HI (excess)?

27. SOCl2 Mg. O

Find out the structure of ‘A’ :

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

X and Y are respectively :

(A) only (B) and

(C) and (D) None of these

(A) 2 (B) 3 (C) 4 (D) 5

MgBr THF+ (X)

35. In the given reaction

H3C (i) Hg(OAc)2/CH3OH

(C) H3C CH CH2 CH3 (D) H3C CH CH2 CH3

Find out ‘A’ of the reaction

39. ; Products of the reaction are :

40. The conversion

Can be effected using :

H3O+ HBr Mg / ether HCHO HI E;

(A) Give yellow ppt, with NaOI

(C) (D) CH CH3

(C) (D) All of these

The final product is :

TsCl alc. KOH OsO4 HIO4

(C) HS–(CH2)5–O–Et (D) HS (CH2)4 CH

50. Final product is ?

Select schemes A, B, C out of

(A) 1° ROH (B) 2° ROH (C) 3° ROH (D) Alkene

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

Identify relationship between products ?

PCl3 PhMgBr Br2 alc.KOH PhCO3H

KMnO4 PhMgBr H2SO4 Cold alkaline

62. Acetone (CH3COCH3) is the major product in :

(A) I, II (B) I, III (C) II, III (D) I, II, III

Multiple Choice Exercise

(A) MeMgBr/H  , H 2SO 4/ , HBr/H 2O 2,h  (B) MeMgBr/H  , H2SO 4/ , HBr

(C) MeMgBr/H  , HBr/CCl4 (D) HBr/H 2O2, MeMgBr/H 

OCH3 OCH3 OCH3

CH3 OTs CH3 H OTs

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

7. Which of the following reaction are not feasible ?

(B) + RO– 

(C) CH3 Br + ROH  CH3 OR

(A) C 6H5 C = CH – C – CH 3 (B) C6H5 C – CH = C – CH3