1.

The decreasing order of bond length of C=C bond in the following compounds is:

I II III IV
(A) II > I > IV > III (B) III > I > II > IV (C) IV > II > I > III (D) IV > I > II > III

2. The longest C–N bond length in the given compound is :

(A) x (B) y (C) z (D) w

3. Select the correct order of heat of hydrogenation ?

(I) (II)

(III) (IV)

(A) I > II > III > IV (B) IV > III > II > I (C) II > III > IV > I (D) II > III > I > IV

4. does not involve :

(A) –p overlap (B) –* overlap (C) p–p overlap (D) p–d overlap

5. Stability of -bond in following alkenes in the increasing order is :

CH3–CH=CH–CH3

(I) (II) (III) (IV)

(A) I < III < IV < II (B) I < II < III < IV (C) IV < III < II < I (D) II < III < IV < I

6. The order of decreasing stability is :

(I) (II) (III) (IV)

(A) IV > I > II > III (B) I > IV > III > II (C) I > II > IV > III (D) IV > II > I > III

7. Give the correct order of magnitude of heat of hydrogenation of the following :

(I) (II) (III) (IV)

(A) I < IV < III < II (B) IV < III < I < II (C) IV < I < III < II (D*) IV < I < II < III

8. Which of the following is the least stable carbanion?

(A) (B) (C) (D)
9. The most stable anion is :

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

10. Arrange the following carbanions in decreasing order of stability :

I II III IV
(A) III > I > IV > II (B) III > II > I > IV (C) I > III > II > IV (D) III > I > II > IV
11. The most stable anion is :

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

12. Arrange the following carbanions in increasing order of stability :

(A) III > IV > I > II (B) I > III > IV > II (C) I > II > III > IV (D) I > IV > III > II

13. The correct basic strength order of following anions is :

(A) > > > > >

(B) > > > > >

(C) > > > > >

(D) > > > > >

14. Which of the following shows the correct order of decreasing basicity in gas phase ?
(A) (CH3)3N > (CH3)2NH > CH3NH2 > NH3 (B) (CH3)2NH > (CH3)3N > CH3NH2 > NH3
(C) (CH3)2NH > CH3NH2 > (CH3)3N > NH3 (D) (CH3)2NH > CH3NH2 > NH3 > (CH3)3N

15. Which of the following cannot be a base?

(A) (B) CH3  C  NH 2 (C) (D)

||
O
16. Select the basic strength order of following molecules ?

(I) Piperidine (II) Pyridine (III) Morpholine (IV) Pyrrole

(A) (IV) > (I) > (III) > (IV) (B) (III) > (I) > (IV) > (II)
(C) (II) > (I) > (III) > (IV) (D) (I) > (III) > (II) > (IV)
17. Arrange the following in increasing order of pKa value ?

(I) (II) (III)

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

18. Select the decreasing order of relative basic strengths of following species :

(I) (II) (III) (IV)

(A) II > IV > I > III (B) III > I > IV > II (C) III > IV > I > II (D) II > I > IV > III

19. Write the order of K a1 values of following acids :

(I) (II) (III)

(A) II > III > I (B) I > III > II (C) III > II > I (D) II > I > III
20. The acid strength order is :

(A) I > IV > II > III (B) III > I > II > IV (C) II > III > I > IV (D) I > III > II > IV

21. (X) (C6H3ClBrCOOH) are a dihalosubstituted benzoic acids. The strongest acid among all
isomers is -

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

22. The order of acidity of the H-atoms underlined in the following compounds is in the order :
(I) (II) (III) (IV)

(A) IV>II>I>III (B) II>IV>III>I (C) III>IV>I>II (D) I>III>II>IV

23. Most acidic hydrogen is present in :

(A) (B) (C) (CH3CO)3CH (D) (CH3)3COH

24. The correct orders are :

(A) > Acid strength

(B) > Acid strength

(C) > Basic strength

(D) > Boiling point

25. Observe the following sequence of reactions :

+ CH3NH2 

(1) + + CH3NH2 +

Select the correct option regarding the relative basic strength (Kb) :

(A) > CH3  C  NH 2 (B) > CH  C  NH

3 2
|| ||
NH NH

(C) CH3  C  NH 2 > CH3NH2 (D) CH3NH2 >

||
NH

26. Order of Ka which can be predicted by following reaction is :

 (A) NH3 > Ph3CH > C2H2 > H2O (B) H2O > HCCH > Ph3CH > NH3
(C) HCCH > H2O > Ph3CH > NH3 (D) Ph3CH > HCCH > H2O > NH3

27. The gases produced in the following reactions are respectively

I : CH3NH2 + NH4Br 

II : CH3SO3H + NaHCO3 

III : CH3  C  NH2 + NaH 

||
O
(A) NH3, NH3, CO2 (B) NH3, SO2, H2 (C) NH3, SO2, NH3 (D) NH3, CO2, H2
28. How many of the following are correct orders for Basic Strength :
S1 : > CH3–NH2 >

S2 : > > C2H5–NH2

S3 : > >

S4 : > >

S5 : > > C2H5–NH2

29. How many of the following compounds give CO2 on reaction with NaHCO3.

, HCl, , , ,

, HCOOH, C2H5–OH, CH3COOH,

 Answer Key
1.(B) 2.(D) 3.(B) 4.(D) 5.(A) 6.(A)
7.(C) 8.(A) 9.(B) 10.(D) 11.(B) 12.(D)
13.(C) 14.(A) 15.(D) 16.(D) 17.(A) 18.(D)
19.(A) 20.(D) 21.(B) 22.(A) 23.(C) 24.(A)
25.(C) 26.(B) 27.(D) 28.4 (S1, S2, S4, S5) 29.6 (i, ii, iii, vi, vii, ix)
 General Organic Chemistry (G.O.C)
Problem solving sheet (PSS)

1. Which order of I effect is incorrect.

 
(I) – N(CH3 )3 > – S(CH3 )2 [–I] (II) –OCH3 > –OH [–I]
(III) –F > –Cl [–I] (IV) –CH3 > – [+I]
(1) II, III & IV (2) III & IV (3) IV only (4) all

2. Select the correct statement ?

(1) All canonical forms always contribute equally to the resonance hybrid.
(2) In both ethanamine and ethenamine nitrogen is sp3 hybridised.
(3) All ‘C–O’ bond length in carbonate dianion are equal.
(4) CH2=C=O does not exhibit resonance because it is not a conjugated system.

3. Select the correct option related to stability of following structures.

(1) > (2) <

O
||
(3) < (4) > CF 3 – C –O

4. The decreasing order of electron density on the ring is :

(I) (II) (III) (IV)

(1) (II) > (III) > (IV) > (I) (2) (IV) > (I) > (II) > (III)
(3) (IV) > (I) > (III) > (II) (4) (I) > (III) > (IV) > (II)

5. The number of hyperconjugable hydrogen atoms of following species are respectively :


(P) (Q) CH3 C HCH2CH3 (R) C=CHCH3 (S) CH3CH=CHC2H5

(1) 3, 5, 9, 8 (2) 3, 5, 9, 5 (3) 5, 5, 3, 5 (4) 5, 2, 6, 5

6. The correct order of increasing basic nature for the bases NH3, CH3NH2 and (CH3)2NH is :
(1) CH3NH2 < NH3 < (CH3)2NH (2) (CH3)2NH < NH3 < CH3NH2
 (3) NH3 < CH3NH2 < (CH3)2NH (4) CH3NH2 < (CH3)2NH < NH3

7. Stability order of the following carbocations is :

   
(I) C6H5 C H2 (II) C6H5CH2 C H2 (III) C6H5 C HCH3 (IV) C6H5 C (CH3)2
(1) II < I < III < IV (2) II < III < I< IV (3) III < I < II < IV (4) IV < III < I < II

8. In the following sets of resonating structure, label the major contributors towards resonance hybrid.

(P) (Q)

(R) (S)

(1)  (2)  (3)  (4) 

9. Which of the following statement is correct regarding dianion of squaric acid ?

(1) In the dianion , all the C–C bonds are of same length but all C–O bonds are of different length.
(2) In the dianion, all C–C bonds are of same length and also all C–O bonds are of same lengths.
(3) In the dianion, all C–C bond lengths are not of same length.
(4) None of the above.

10. The decreasing order of basicity of the following amines is:

NH2 NH2
N
(I) (II) (III) (IV)
N
H
(1) (II) > (III) > (IV) > (I) (2) (I) > (III) > (IV) > (II)
(3) (III) > (II) > (I) > (IV) (4) (III) > (I) > (II) > (IV)

11. Hyperconjugation observed in


(1) (2) CPh3 (3) (4)

12. Correct stability order for :

(I) (II)

(1) I > II (2) II > I (3) II = I (4) Can’t be predicted

13. Identify the most stable carbocation among the following :

 (1) (2) (3) (4)

14. Which of the following benzene ring has greater electron density than

(1) (2) (3) (4)

15. Compare C–N bond length in the following :

(1) I > II > III (2) I > III > II (3) III > II > I (4) III > I > II

16. Which is not stable at room temperature ?

(1) (2) (3) (4)

17. Correct order of stability of following alkenes is

(1) I > II > III (2) I > III > II (3) III > II > I (4) III > I > II

18. In the following benzyl/allyl system

R – CH = CH2 and

(R is alkyl group)
decreasing order of inductive effect is :
(1) (CH3)3 C— > (CH3)2CH— > CH3CH2— (2) CH3CH2— > (CH3)2CH— > (CH3)3C—
(3) (CH3)2CH— > CH3CH2— > (CH3)3C— (4) (CH3)3C— > CH3CH2— > (CH3)2CH—

19.

The most stable canonical structure of this molecule is :

 (1) (2)

(3) (4) All are equally stable

20. In the anion HCOO– the two carbon-oxygen bonds are found to be of equal length. What is the reason
for it?
(1) electronic orbitals of carbon atom are hybridised
(2) the C = O bond is weaker than the C – O bond
(3) the anion HCOO– has two equivalent resonating structures
(4) the anion is obtained by removal of a proton from the acid molecule.

21. The aromatic compound would be

(1) (2) (3) (4)

22. Match the resonance energies 67, 88 and 121 kJ mol–1 for the following compounds.

O N S

H
I II III
(1) I - 67, II -121, III-88 (2) I -121, II-67, III- 88
(3) I - 67, II - 88, III-121 (4) I - 121, II - 88, III - 67

23. The most Carbocations, carbanions, free radicals and radical cation are reactive carbon intermediates.
Their hybrid orbitals respectively are
(1) sp2, sp2, sp3, sp (2) sp2,sp2, sp, sp3 (3) sp2, sp3, sp2, sp (4) sp3, sp2, sp, sp2

24. Rank the following radicals in order of decreasing stability.

(I) (II) (III) (IV)

(1) III > II > I > IV (2) III > II < I < IV (3) II > III > II > IV (4) III < II < I < IV

25. Among the following the strongest acid is :

(1) HC  CH (2) C6H6 (3) C2H6 (4) CH3OH

26. Which of the following carbocation is most stable?

(1) (2) (3) (4)

27. The correct pKa order of the following acids is

I II III
(1) I > II > III (2) I > III > II (3) III > II > I (4) III > I > II

28. Arrange the following carbanions in decreasing order of stability :

I II III IV
(1) IV > III > I > II (2) IV > II > III > I (3) IV > III > II > I (4) III > IV > II > I

29. Which of the following compounds will show tautomerism :

(1) 2, 2-Dimethyl propanal (2) Benzaldehyde
(3) Acetyl acetone (4) Benzophenone

30. In which pairs first compound is stronger acid than the second ?
(1) Adipic acid, succinic acid (2) Fumaric acid, maleic acid
(3) Phthalic acid, terepthalic acid (4) o–toluic acid, Salicylic acid

31. Arrange the following compounds in the increasing order of basicity.

(1) III > I > IV > II (2) III > IV > I > II (3) II > I > IV > III (4) I > II > III > IV

32. Select the decreasing order of relative basic strength of following species :

(I) (II) (III) (IV)

(1) (II) > (IV) > (I) > (III) (2) (III) > (I) > (IV) > (II)
(3) (III) > (IV) > (I) > (II) (4) (II) > (I) > (IV) > (III)
33. Which of the following reaction is possible ?
(1) EtOH + CH3COONa  EtONa + CH3COOH
O O
|| ||
(2) CH3  C  OH + CH3SO3Na 
 CH3  C  ONa + CH3SO3H
O O O O
|| || || ||
(3) CH3  C  OH + H  C  ONa 
 CH3  C  ONa + H  C  OH
 (4)

34.

in C1–H, C2–H and C3–H the homolytic bond dissociation energy order is :
(1) C2–H > C3–H > C1–H (2) C2–H > C3–H > C1–H
(3) C2–H > C3–H > C1–H (4) C3–H > C2–H > C1–H

35. In which of the following carbocation rearrangement will not take place?

(1) (2) (3) (4)

36. At normal temperature, X and Y are

OH
O

OH
O
X Y
(1) resonance structures (2) tautomers
(3) functional isomers (4) positional isomers

37._ Select correct statement from the following :

(1) is more basic than (2) is more acidic than

(3) HCCH is more acidic than NH3 (4) is more stable than

38._ Which is correct decreasing order of acidic strength of following compounds ?

(1) (i) > (iii) > (iv) > (ii) (2) (i) > (iv) > (iii) > (ii) (3) (iii) > (i) > (iv) > (ii) (4) (iv) > (iii) > (i) > (ii)

39._ Which is most basic in aqueous solution ?

 (1) CH3NH2 (2) (CH3)2NH (3) (CH3)3N (4) Ph–NH2

40. Give the correct order of decreasing acidity :

(i) C2H5–SH (ii) C2H5–OH (iii) C2H5NH2 (iv) CH3–CH2–CH3
(1) (ii) > (i) > (iii) > (iv) (2) (iii) > (ii) > (i) > (iv) (3) (i) > (ii) > (iii) > (iv) (4) (iii) > (iv) > (ii) > (i)

41. Which of the following has the shortest C–Cl bond?

(1) Cl–CH=CH–NO2 (2) Cl–CH=CH–CH3 (3) Cl–CH=CH2 (4) Cl–CH=CH–OCH3

42. The correct order of acidity for the following compound is

(1) Benzoic acid > phenol > p-nitrobenzoic acid > m-nitrobenzoic acid.
(2) phenol > p-nitrobenzoic acid > m-nitrobenzoic acid > benzoic acid.
(3) p-nitrobenzoic acid > m-nitrobenzoic acid > benzoic acid > phenol.
(4) m-nitrobenzoic acid > p-nitrobenzoic acid > benzoic acid > phenol.

43. The correct order of acidity of the C-H proton is –

(1) acetylene > ethylene > ethane (2) ethylene > acetylene > ethane
(3) ethane > ethylene > acetylene (4) acetylene > ethane >.ethylene

44. Which one of the following compounds can be deprotonated by OH– fastest ?
(1) HCOOH, pKa = 3.8 (2) H2S, pKa = 7.0
(3) Toluene, pKa = 41 (4) CH3NH2, pKa = 40

45. The pKa values of the acids A to D are found to be 4.19, 3.41, 4.46 and 4.76. The acid having pKa of
3.41 is

(1) (2) CH3COOH (3) (4)

56. Which of the following would be expected to be easily dissociate in water ?

(1) ClCH2CH2CH2COOH (2) CH3CCl2CH2COOH
(3) CH3CH2CCl2COOH (4) CH3CH2CHClCOOH

57. Which of the following substituents will decrease the acidity of phenol -
(1) –NO2 (2) –CN (3) –CH3 (4) –CHO

58. Select the compound having maximum pKa

(1) Phenol (2) Ethyl alcohol (3) Formic acid (4) Cyanoacetic acid

59. Which of the following is weakest acid ?

(1) CH3CHFCOOH (2) FCH2CH2COOH (3) ClCH2CH2COOH (4) CH3CH(Cl)COOH

60. Among the following which is least acidic ?

(1) p-Nitrophenol (2) p-Chlorophenol (3) Phenol (4) o-Cresol
22. The correct order of + m effect of ‘N’ containing functional group on benzene ring, amongst the given
compounds is
 PSS Answers
1. (3) 2. (3) 3. (3) 4. (3) 5. (2) 6. (3) 7. (1)

8. (3) 9. (2) 10. (3) 11. (4) 12. (1) 13. (3) 14. (3)

15. (1) 16. (3) 17. (3) 18. (1) 19. (3) 20. (3) 21. (3)

22. (3) 23. (3) 24. (1) 25. (4) 26. (1) 27. (3) 28. (3)

29. (3) 30. (3) 31. (2) 32. (4) 33. (4) 34. (4) 35. (2)

36. (2) 37._ (3) 38._ (2) 39._ (2) 40. (3) 41. (1) 42. (3)

43. (1) 44. (1) 45. (3) 46. (3) 47. (3) 48. (2) 49. (3)

50. (4) 51. (3) 52. (1) 53. (4) 54. (2) 55. (4)