EXERCISE-I (Conceptual Questions) BUILD UP YOUR UNDERSTANDING

1. The inductive effect :

(1) Implies the atom’s ability to cause bond polarization
(2) Increases with increase of distance
(3) Implies the transfer of lone pair of electrons from more electronegative atom to the lesser electronegative
atom in a molecule
(4) Implies the transfer of lone pair of electrons from lesser electronegative atom to the more electronegative
atom in a molecule

2. Arrange basic strength of the given compounds in decreasing order :

(a) CH3–CH2–NH2 (b) CH2=CH–NH2 (c) [C6H5–NH2]
(1) a > b > c (2) a > c > b (3) c > b > a (4) b > c > a

3. Which is most acidic compound :

(1) C2H5COOH (2) CH3CH2CH2COOH (3) CH3COOH (4) HCOOH

4. Which of the following groups has the highest +I effect :

(1) CH3— (2) CH3CH2— (3) (CH3)2 CH— (4) (CH3)3 C—

5. Maximum –I effect is exerted by the group

(1) –C6H5 (2) –OCH3 (3) –Cl (4) –NO2

6. Pair of groups exerting (–I) effect is :

(1) –NO2 and –CH3 (2) –NO2 and –Cl (3) –Cl and –CH3 (4) –CH3 and –C2H5

7. Arrange in their Acidic strength order :

OH

H 2O C2H 5OH
I II III
(1) I > II > III (2) II > I > III (3) III < II > I (4) II < III < I
8. Arrange the following in Increasing order of their basicity :
HO–, CH3COO– Cl–
I II III
(1) III > II > I (2) III < II < I (3) II < III < I (4) II < III > I

9. The order of stability of the following resonating structures is:


O O O

CH2=CH–CH CH2 –CH=CH CH2 –CH=CH
I II III
(1) II > I > III (2) I > III > II (3) I > II > III (4) III > II > I

10. Most stable carbocation is :

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   
(1) CH2=CH (2) CH 2=CH–CH 2 (3) CH 2 (4)  CH 2

11. Which of the following is most stable :

   
(1) CH3 (2) CH3– CH 2 (3) CH3– CH –CH3 (4) CH2=CH– CH 2
12. Which of the following is least stable carbocations :
   
(1) CH2= CH (2) CH3– CH 2 (3) (Ph)2 C H (4) Ph CH 2
13. Which of the following is most stable :

(1) CH3 (2) CH2= CH (3) CH C (4) CH3–C C

14. Which one of the carbanions is most stable :

CH 2 CH2
CH 2 CH 2
(1) NO 2 (2) (3) CN (4)
NO2 CN
15. What is the decreasing order of strength of the bases,

OH, NH2 , , CH3–CH2

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

16. The stability of given free radicals in decreasing order is :

. .
(a) CH3–CH2 (b) CH3–CH–CH3 (c) H3C—C—CH 3 (d) CH3
CH3
(1) c > d > a > b (2) a > b > c > d (3) c > b > d > a (4) c > b > a > d

17. Correct order of stability is :

(1) CH2=CH2 > CH3–CH=CH2 > (CH3)2C=CH2 (2) CH2=CH2 < CH3–CH=CH2 < (CH3)2C=CH2
(3) CH2=CH2 < (CH3)2C=CH2 < CH3–CH=CH2 (4) CH3–CH=CH2 < CH2=CH2 < (CH3)2C=CH2

18. Arrange the Stability of following :

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

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

20. Which of the following substituted carboxylic acids has the highest Ka value :
(1) CH3–CH2 –CH–COOH (2) CH3–CH–CH2 –COOH
Cl Cl

(3) CH2 –CH2 –CH2–COOH (4) CH3–CH–CH2 –COOH

Cl Br

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21. Choose the most stable Carbocation :
 
(1) CH3–CH=CH– CH2 (2) CH2=CH–CH –CH3
 
(3) CH2=C –CH2–CH3 (4) CH2=CH–CH2 – CH2

22. Which of the following is not the resonance contributor for phenoxide ion :

O O O O

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



23. Most stable carbonium ion in the following will be:


(1) (2)  (3) CH2 (4) 

24. Consider the following three halides :

(A) CH3–CH2–Cl (B) CH2=CH–Cl (C) C6H5–Cl
Arrange C–Cl bond length of these compound in decreasing order :
(1) A > B > C (2) A > C > B (2) C > B > A (4) B > C > A
25. Consider the following compounds :
NH2 NH2 NH2 NH2

NO2 Cl CH3
(a) (b) (c) (d)

Arrange these compounds in decreasing order of their basicity :

(1) a > b > c > d (2) b > c > a > d (3) d > a > c > b (4) d > a > b > c

26. Which free radical is the most stable :

(1) C 6H 5–CH 2 (2) CH2=CH–CH2 (3) CH 3–CH–CH 3 (4) CH 3–C–CH3

CH3
27. Electromeric effect :
(1) comes into play at the demand of attacking reagent.
(2) involves displacement of electrons in a sigma bond.
(3) comes into play in the molecule when at least one atom has unshared pair of electrons.
(4) is permanent effect.
28. Which statement is correct for electromeric effect:
(1) It is a temporary effect
(2) It is the property of  bond
(3) It takes place in presence of reagent, i.e., electrophile or nucleophile
(4) All are correct

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29. Which is most acidic compound :

COOH
COOH COOH COOH
CH3
(1) (2) (3) (4)
CH3 CH3

30. Consider the hydrogen atoms attached to three different carbon atoms (labeled 1, 2 & 3). Rank the attached
hydrogen atoms in order from most acidic to least acidic :

(1) 1 > 2 > 3 (2) 2 > 1 > 3 (3) 2 > 3 > 1 (4) 3 > 2 > 1
31. Which nitrogen is protonated readily in the guanidine?

2
NH2
NH
1 NH2
3

(1) 1 (2) 2 (3) 3 (4) All with equal rate

32. CH2=CH–CH=CH2
1 2 3 4
The bond between C2 – C3 is shorter than C–C single bond because :
(1) Resonance (2) Inductive (3) Electromeric (4) Hyper conjugative
33. Examine the following two structures for the anilinium ion and choose the correct statement from the ones
given below.
 NH 3
NH3


I II
(1) II is not an acceptable canonical structure because carbonium ions are less stable than ammonium ion.
(2) II is not an acceptable canonical structure because it is non-aromatic.
(3) II is not an acceptable canonical structure because the nitrogen has 10 valence electrons.
(4) II is an acceptable canonical structure.
34. Which of the following shows the correct order of decreasing acidity :

(1) PhCO2H > PhSO3H > PhCH2OH > PhOH (2) PhSO3H > PhOH > PhCO2H > PhCH2OH

(3) PhCO2H >PhOH > PhCH2OH > PhSO3H (4) PhSO3H > PhCO2H > PhOH > PhCH2OH

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35. (A) N (B) (C)
H N
NH2
Choose the incorrect statement :
(1) A is more basic than C (2) B is more basic than A
(3) B is more basic than C (4) All are aromatic bases
36. The strongest base is :

(1) (2) (3) (4) CH3–NH–CH3

37. Increasing order of the stability is :

CH3
CH3CH=CH2 CH3CH2CH=CH2, CHCH=CH2 (CH3)3CCH=CH2
CH3

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

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

38. (I) NH2 (II) CH3O NH2

NH2
(III) NO2 NH2 (IV)
NO2

The correct order of decreasing basicity of the above compound is :

(1) I > II > III > IV (2) II > I > IV > III (3) III > IV > II > I (4) II > I > III > IV
39. Among the following alkenes

1-butene trans-2-butene cis-2-butene Isobutene

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

the order of decreasing stability is :

(1) II > I > III > IV (2) III > IV > I > II (3) IV > I > II > III (4) IV > III > II > I
40. In which of the following keto-enol systems the enol state is more stable than the keto state :

(1) (2)

(3) (4) All the above

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41.

The basic strength of I, II and III decreases in the order

(1) I > II > III (2) III > II > I (3) II > I > III (4) I > III > II
42. Which of the following represent the decreasing order of Ka values ?

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

43. The order of acidic strength of the hydrogen atoms (H, H, H) in the given molecule is :

(1) H > H > H (2) H > H > H (3) H > H > H (4) H > H > H

44. Which of the following  bonds (C–H) participate in hyperconjugation :

(II)
H CH2–H
(I)

(IV)
H
(III ) (V)
H H
(1) II, III, IV (2) I, IV, V (3) I, II, IV, V (4) II, IV, V

45. What is the order of extent to dissolve the given compound in following solvents :
Compound Solvents

H2 O
EtOH
Et 2 O

(1) H2O > EtOH > Et2O (2) Et2O > EtOH > H2O
(3) H2O > Et2O > H2O (4) EtOH > Et2O >H2O

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46. The most stable canonical structure among the given structure is :

NH
NH NH

(a) (b) (c)

(1) a (2) b (3) c (4) All are equally stable

47. Arrange the following compounds in decreasing order of acidity ?

Cl
Cl
(I) C6H5–OH (II) (III) (IV)

OH OH

Select the correct answer from the codes given below :

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

48. Which of the following is weakest acid ?

COOH
COOH

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

OH
49. Among the following the compound having the most acidic alpha-hydrogen is :

(1) CH3CHO (2) CH3COCH3 (3) (4) CH3–CO–CH2–CO2CH3

50. Arrange pKa of the given compounds in decreasing order :

(I) Phenol (II) Ethyl alcohol (III) Formic acid (IV) Benzoic acid
(1) I > II > III > IV (2) II > I > IV > III (3) III > II > IV > I (4) IV > III > I > II

51. Arrange acidity of given compounds in decreasing order :


(I) CH3–NH–CH2–CH2–OH (II) CH3–NH–CH2–CH2–CH2–OH (III) CH3 3 N– CH2 – CH 2 – OH

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

52. Which of the following is most basic :

Me Me
NH2 N
CH3 Me Me
(1) (2) (3) (4)

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53. Which of the following alkene is most stable :

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

54. Which of the following is aromatic :

.. H H
(1) (2) (3) (4) N

55. Which of the following resonance structures contributes is the most stable ?

OCH3 OCH3
OCH3 ||
(1) (2) (3) (4)

56. Which of the following compounds has the most basic nitrogen ?
O
O O ||
|| ||
..
a. b. .. c. .. d. N O
N N ||
H
||

H O O
(1) a (2) b (3) c (4) d

57. Which of the following group has (+M) effect ?

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

58. Compare heat of hydrogenation of the following :

(i) (ii) (iii)

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

59. Which of the following compounds will not give effervescence with sodium bicarbonate ?

OH
NO2 SO3H
NO2
(1) C6H5CO2H (2) (3) C6H5OH (4)

NO2

60. Give the decreasing order of hyperconjugative effect of R in R–CH = CH2, where R is :

Page # 9
 I. Me – II. Et– III. Me2CH– IV. Me3C–
(1) I > II > III > IV (2) IV > III > II > I (3) II > I > III > IV (4) IV > III > I > II

61. The decreasing order of acidic characters of the following is :

I. CH  CH II. III.

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

62. The increasing order of pKb values of the following is :

I. HC  C II. H III. NH2 IV. CH3

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

63. Which of the following molecules, in pure form, is (are) unstable at room temperature ?
O

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

64. The compound that does not liberate CO2, on treatment with aqueous sodium bicarbonate solution, is :

(1) Benzoic acid (2) Benenesulphonic acid

(3) Salicylic acid (4) Carbolic acid

65. Considering the basic strength of amines in aqueous solution, which one has the smallest pKb value ?

(1) (CH3)3N (2) C6H5NH2 (3) (CH3)2NH (4) CH3NH2

66. In benzene C–C bond length between all carbons are equal because of :

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 (1) Tautomerism (2) sp2 hybridization (3) Isomerism (4) Resonance

67. Correct order of acidic strength is :

(1) HCOOH > CH3COOH > C2H5COOH (2) C2H5COOH > CH3COOH > HCOOH

(3) HCOOH > C2H5COOH > CH3COOH (4) CH3COOH > HCOOH > C2H5COOH

68. In the following benzyl / alkyl system

R – CH = CH2 or R

(R is alkyl group)

Correct order of inductive effect is :

(1) (CH3)3C— > (CH3)2CH— > CH3CH2— (2) (CH3CH2— > (CH3)2CH— > (CH3)3C—

(3) (CH3)2CH— > CH3CH2— > (CH3)3C— (4) (CH3)3C— > CH3CH2— > (CH3)2CH—

69. The correct order of increasing basic strength of the bases NH3, CH3NH2 and (CH3)2NH is :

(1) NH3 < CH3NH2 < (CH3)2NH (2) CH3NH2 < (CH3)2NH < NH3

(3) CH3NH2 < NH3 < (CH3)2NH (4) (CH3)2NH < NH3 < CH3NH2

70. Which of the following is the strongest base :

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

71. The increasing order of stability of the following free radicals is :

       
(1) (C6H5)3 C <(C6H5)2 CH <(CH3)3 C <(CH3)2 CH (2) (C6H5)2 CH <(C6H5)3 C <(CH3)3 C <(CH3)2 CH

       
(3) (CH3)2 CH <(CH3)3 C <(C6H5)3 C <(C6H5)2 CH (4) (CH3)2 CH <(CH3)3 C <(C6H5)2 CH <(C6H5)3 C

72. The correct order of increasing acid strength of the compounds :

(a) CH3CO2H (b) MeOCH2CO2H (c) CF3CO2H (d)

(1) d < a < c < b (2) d < a < b < c (3) a < d < c < b (4) b < d < a < c

73. Which one of the following is the strongest base in aqueous solution ?

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 (1) Trimethylamine (2) Aniline (3) Dimethylamine (4) Methylamine

74. Which of the following acids has the smallest dissociation constant :
(1) CH3CHFCOOH (2) FCH2CH2COOH (3) BrCH2CH2COOH (4) CH3CHBrCOOH

75. Which of the following is least stable

(1) (2)

(3) (4)

76. Among the following, the least stable resonance structure is :

O O
 
(1) (2) (3)  N (4)  N

O O

77. The correct acidity order of the following is :

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

78. The correct order of increasing basicity of the given conjugate bases (R = CH3) is :

(1) RCOO < < NH2 < R (2) RCOO < < R < NH2

(3) R < < RCOO < NH2 (4) RCOO < NH2 < < R

79. Amongst the following, the total number of compounds soluble in aqueous NaOH is :

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

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 80. Hyperconjugation involves overlap of the following orbitals :

(1)  –  (2)  – p (3) p – p (4) – 

ANSWER KEY [EXERCISE-I]

Que. 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15
Ans. 1 1 4 4 4 2 1 2 3 4 4 1 3 1 1
Que. 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30
Ans. 4 2 3 3 1 2 4 3 1 3 1 1 4 2 2
Que. 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45
Ans. 1 1 3 4 1 2 1 2 4 4 2 1 4 4 2
Que. 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60
Ans. 3 4 2 3 2 1 4 3 3 4 1 3 2 3 1
Que. 61 62 63 64 65 66 67 68 69 70 71 72 73 74 75
Ans. 2 4 2 4 3 4 1 1 1 4 4 2 3 3 3
Que. 76 77 78 79 80
Ans. 1 1 1 4 2

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 EXERCISE-II (Previous Year Questions) AIPMT & AIIMS

AIPMT-2000
1. Polarization in acrolein as :

 – –  –   –
(1) CH2 = CH –CHO (2) CH2 = CH –CHO (3) CH2 =CH– CHO (4) CH2 =CH– CHO

2. Correct order of stability is :

(1) 1-butene > trans-2-butene > cis-2-butene (2) trans-2-butene > 1-butene > cis-2-butene
(3) trans-2-butene > cis-2-butene > 1-butene (4) cis-2-butene > trans-2-butene > 1-butene

AIPMT-2002

3. and are :

(1) Resonating structures (2) Tautomers

(3) Geometrical isomers (4) Optical isomers

AIPMT-2003
4. Which of the following order of acidic strength is correct :
(1) RCOOH > ROH > HOH > HCCH (2) RCOOH > HOH > ROH > HCCH
(3) RCOOH > HOH > HCCH > ROH (4) RCOOH > HCCH > HOH > ROH

AIIMS-2003

5. Among the following the weakest base is :

(1) C6H5CH2NH2 (2) C6H5CH2NHCH3 (3) O2NCH2NH2 (4) CH3NHCHO

6. Among the following strongest acid is :

(1) CH3COOH (2) C6H5COOH (3) m-CH3OC6H4COOH (4) p-CH3OC6H4COOH

AIIMS-2004
7. The strongest base among the following is :

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

8. Among the following the dissociation constant is highest for :

(1) C6H5OH (2) C6H5CH2OH (3) CH3CCH (4) CH3NH3+Cl–

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9. Among the following the aromatic molecule is :

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

AIPMT-2005
10. Which amongst the following is the most stable carbocation :



(1) CH3CH2 (2) CH3 (3) (4)

11. Which one of the following compounds is most acidic :

OH
(1) (2) (3) (4) ClCH2CH2OH

AIIMS-2005
12. Pyridine is less basic than triethylamine because

(1) Pyridine has aromatic character

(2) Nitrogen in pyridine is sp2 hybridized

(3) Pyridine is a cyclic system

(4) In pyridine, lone pair of nitrogen is delocalized

AIPMT-2006
13. Which of the following is more basic than aniline:

(1) Diphenyl amine (2) Triphenyl amine (3) p-nitro aniline (4) Benzyl amine
AIPMT-2007
14. Which of the following presents the correct order of the acidic strength in the given compounds :

(1) FCH2COOH > CH3COOH > BrCH2COOH > ClCH2COOH

(2) BrCH2COOH> ClCH2COOH > FCH2COOH > CH3COOH

(3) FCH2COOH >ClCH2COOH > BrCH2COOH > CH3COOH

(4) CH3COOH > BrCH2COOH > ClCH2COOH > FCH2COOH

AIPMT-2008
15. The stability of carbanions in the following :

(a) RCC (b) (c) (d)

is in the order of :

(1) (d)>(b)>(c)>(a) (2) (a)>(c)>(b)>(d) (3) (a)>(b)>(c)>(d) (4) (b)>(c)>(d)>(a)

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 AIPMT-2010
16. Given are cyclohexanol (I), acetic acid (II) 2,4,6-trinitrophenol (III) and phenol (IV). In these the order of
decreasing acidic character will be :
(1) III > II > IV > I (2) II > III > I > IV (3) II > III > IV > I (4) III > IV > II > I

17. Which one of the following compounds has the most acidic nature

CH2 OH OH OH
(1) (2) (3) (4)

AIPMT-2012
18. The correct order of decreasing acid strength of trichloroacetic acid (A), trifluoroacetic acid (B), acetic acid
(C) and formic acid (D) is :

(1) B > A > D > C (2) B > D > C > A (3) A > B > C > D (4) A > C > B > D

NEET-2013
19. Some meta-directing substituents in aromatic substitution are given. Which one is most deactivating ?

(1) –CN (2) –SO3H (3) –COOH (4) –NO2

AIIMS-2013
20. Which of the following compounds possesses the C—H bond with the lowest bond dissociation energy?

(1) Toluene (2) Benzene (3) n-pentane (4) 2,2-dimethyl propane

AIPMT-2014
21. What products are formed when the following compound is treated with Br2 in the presence of FeBr3 ?

CH3

CH3

CH3
CH3 CH3 CH3
Br Br Br
(1) and (2) and
CH3
CH3 Br CH3 CH3

CH3 CH3
CH3 CH3
Br
(3) and (4) and
CH3 CH3
CH3 Br Br Br CH3

22. Which of the following will not be soluble in sodium hydrogen carbonate ?
(1) 2, 4, 6-trinitrophenol (2) Benzoic acid (3) o-nitrophenol (4) Benzenesulphonic acid

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 AIPMT-2015
23. Consider the following compounds

Hyperconjugation occurs in :
(1) II only (2) III only (3) I and III (4) I only

NEET-1 2016
24. The correct statement regarding the basicity of arylamines is :

(1) Arylamines are generally less basic than alkylamines because the nitrogen lone-pair electrons are
delocalized by interaction with the aromatic ring  electron system

(2) Arylamines are generally more basic than alkylamines because the nitrogen lone-pair electrons are not
delocalized by interaction with the aromatic ring  electron system.

(3) Arylamines are generally more basic than arylamines are generally more basic than alkylamines
because of aryl group.

(4) Arylamines are generally more basic than alkylamines, because the nitrogen atom in arylamines is sp-
hybridized.

25. The pair of electron in the given carbanion, , is present in which of the following orbitals ?

(1) 2p (2) sp3 (3) sp2 (4) sp

NEET-II 2016
26. The correct order of strengths of the carboxylic acid :

is :

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

AIIMS-2016

27. Arrange the following compounds in increasing order of acidic strength :

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

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28. Arrange the following compounds in order of their boiling points :

(1) I > II > III (2) III > II > I (3) II > I > III (4) III > I > II
NEET-2017
29. The correct increasing order of basic strength for the following compounds is :

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

NEET-2018
30. Which of the following is correct with respect to – effect of the substituents? (R=alkyl)

(1) –NH2 < – OR < – F (2) –NR2< – OR < – F (3) –NH2> – OR > – F (4) –NR2 > – OR > – F

31. Which of the following carbocations is expected to be most stable?

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

32. Carboxylic acids have higher boiling points than aldehydes, ketones and even alcohols of comparable

molecular mass. It is due to their :

(1) Formation of intramolecular H-bonding

(2) Formation of carboxylate ion

(3) More extensive association of carboxylic acid via van der Waals force of attraction

(4) Formation of intermolecular H-bonding

ANSWER KEY [EXERCISE-II]

Q ue. 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15
An s. 4 3 1 2 4 3 3 4 1 3 1 2 4 3 3
Q ue. 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30
An s. 1 2 1 4 1 3 3 2 1 4 4 1 2 4 1,2
Q ue. 31 32
An s. 3 4

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 EXERCISE-III ANALYTICAL QUESTIONS

1. Mesomeric effect is the resonance of :

(1) - electrons and lone pair (2) - electrons only
(3)  and -electrons both (4) -electrons only

2. Which of the following is most stable carbocations

CH 3
   
(1) CH3 (2) CH3– CH 2 (3) CH3–C=O (4) CH 3–C– CH2
CH 3

3. Which of the following is most stable :

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

4. Arrange stability of the given carbocations in decreasing order :

   
CH2 CH2 CH2 CH2

OCH3 OH NH2 Cl
I II III IV
(1) I > II > III > IV (2) III > II > I > IV (3) IV > I > II > III (4) III > I > II > IV

5. In the anion HCOO–, the two carbon-oxygen bonds are found to be equal length. What is the reason for it :
(1) the C=O bond is weaker than the C–O bond
(2) the anion HCOO– has two equivalent resonating structures
(3) the electronic orbitals of carbon atom are hybridized
(4) the anion is obtained by removal of proton
from the acid molecule
6. Hyperconjugation involves overlaping of :
(1)  M.O. with ‘s’ (2) ‘p’ orbital with p orbital
(3)  M.O. with  M.O. (4)  M.O. with  M.O.

7. 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

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8. Which of the following is wrong about resonance:
(1) Resonating structures having same energy have same contribution
(2) All resonating structures have same number of unpaired electron.
(3) All resonating structures have same number of bond pair electrons.
(4) All resonating structures have same amount of net charge.

9. Which of the following statement is correct about arrow headed ‘C’ of

(1) Negative charge is delocalised due to sp2 hybridisation

(2) sp2 hybridised but (–)ve charge is localised
(3) sp3 hybridised and (–) ve charge is not delocalised.
(4) sp3 hybridised and (–) ve charge is delocalised.

10. Which of the following is not correct statement:

(1) is a stronger base than (2) is more basic than

(3) NH2OH is less basic than NH3 (4) CHC is less basic than CH 2 =CH
11. Which has localized ve charge :
  
NH3 CH2 CH 3 CH2

(a) (b) (c) (d) H 2N–C=NH 2
NH 2
(1) a, d (2) a, c (3) c, d (4) b, d

12. What is the correct increasing order of bond lengths of the bonds indicated as I, II, III and IV in following
compounds :
II III IV

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

13. Which is the decreasing order of acidity in,

(I) HCOOH (II) CH3COOH (III) CH3CH2COOH (IV) C6H5COOH
(1) I > II > III > IV (2) IV > III > II > I (3) IV > I > II > III (4) I > IV > II > III

14. Which is most stable carbocation :



(1) (2) C (3) CH2=CH–CH2 (4) 

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15. Which is most stable carbanion :

CH2

(1) (2) (3) (4) CH2=CH– CH –CH=CH2

16. Which is most stable species :

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

17. Rank the hydrogen atoms according to their acidic strength :

(1)  >  >  (2)  >  >  (3)  >  >  (4)  >  > 

18. Which is most stable carbocation :


(1) C (2) (3) (4)

19. Arrange the following in correct order of acidic strength :

(I) CH3–NO2 (II) NO2–CH2–NO2 (III) CH3–CH2–NO2 (IV)

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

20. (I) (II) (III)

Compare carbon-carbon bond rotation across I, II, III.

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

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21.

The correct order of decreasing basic strengts of x, y and z is:

(1) x > y > z (2) x > z > y (3) y > x > z (4) y > z > x

22. Consider the following compounds

CH3CH2NH2 CH3 NH2

I II III
Correct order of their basic strength is :
(1) I < II < III (2) II > I > III (3) III > II < I (4) II < III < I
23. Arrange the following in decreasing of their basic nature :
NH2

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

24. Give the correct order of increasing acidity of the following compounds :

(I) OH (II) OH (III) COOH (IV) C CH

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

25. Which of the following shows the correct order of stability :

     
(1) CH3 O C HCH3 < CH3O C H2 < CH3 CH2 C H2 (2) CH3 CH2 C H2 < CH3 O C HCH3 < CH3O C H2
     
(3) CH3 C HCH3 < CH3O C H2 < CH3 O C HCH3 (4) CH3O C H2 < CH3 O C HCH3 < CH3 CH2 C H2

26. Which of the following shows the correct order of decreasing stability :
   
(1) CH3 CH2 > CH3O CH2 > CH2 > CH3– CH2

   
(2) CH3O CH2 > CH3 CH2 > CH2 > CH 3 –CH 2

   
(3) CH2 > CH3O CH2 > CH3 CH2 > CH – CH
3 2

   
(4) CH3O CH2 > CH2 > CH – CH > CH3
3
CH2
2

Page # 22
27. Which of the following is most stable resonating structure of anthracene ?

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

28. Give the correct order of increasing acidity of the hydrogen bonded to nitrogen in the following compounds :

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

29. Which is incorrect statement :

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

(3) is less stable than (4) is less reactive than towards ESR.

30. The hybridization states of the nitrogen atoms in pyridine, piperidine and pyrrole are respectively :

N N
N
H H
Pyridine Piperdine Pyrrole

are respectively :
(1) sp2, sp3 and sp2 (2) sp2, sp3 and sp3 (3) sp3, sp3 and sp3 (4) sp2, sp2 and sp2

31. What is the correct order of base strength of indicated sites :

O
a
H2N
c
CN
b d
H2N NH2

(1) a > b > c > d (2) d > c > a > b (3) d > c > b > a (4) c > d > a > b

Page # 23
 O
Ha
32. What is the order of acidic strength of the labelled H atoms :
Hb
Hc

(1) Ha > Hc > Hb (2) Hb > Hc > Ha (3) Hc > Ha > Hb (4) Ha > Hb > Hc

33. Increasing order of base strength of the following is :

I. CH3NH2 II. (CH3)2NH III. (CH3)3N
IV. C6H5NH2 V. C6H5CH2NH2
(1) IV < V < I < II < III (2) IV < V < III < I < II
(3) IV < III < V < I < II (4) IV < V < I < III < II
34. Which of the following compounds exhibit tautomerism :

(1) (2) (3) (CH3)2CH–NO2 (4) All

35. An alcohol, an aldehyde and a carboxylic acid of comparable mass will have their boiling points in the order

(1) Alcohol < Aldehyde < Carboxylic acid (2) Aldehyde < Alcohol < Carboxylic acid

(3) Alcohol < Carboxylic acid < Aldehyde (4) Carboxylic acid < Aldehyde < Alcohol

36. Which of the following compound is not resonance stabilized ?

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

37. Which of the following is strongest base ?

NH

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

38. Among the given compounds, the most susceptible to nucleophilic attack at the carbonyl group is :

(1) CH3COCl (2) CH3COOCH3 (3) CH3CONH2 (4) CH3COOCOCH3

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39. When –CH3, & groups are introduced on benzene ring then correct order of their

electronic effect is :

(1) (2)

(3) (4)

40. Arrange the carbanions, , , , , in order of their decreasing stability :

(1) > > > (2) > > >

(3) > > > (4) > > >

41. The correct order of basicities of the following compounds is :

NH
(A) CH3 C (B) CH3CH2NH2 (C) (CH3)2NH (D)
NH2

(1) B > A > C > D (2) A > C > B > D (3) C > A > B > D (4) A > B > C > D

42. Order of rate of reaction of following compound with phenyl magnesium bromide is :

(I) (II) (III)

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

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43.

Correct order of acidic strength is :

(1) x > y > z (2) z > y > x (3) y > z > x (4) x > z > y

44. The correct stability order of the following resonance structures is :

H2C=N=N H2C–N=N H2C–NN H2C–N=N

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

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

45. The total number of contributing structures showing hyperconjugation (involving C—H bonds) for the following
carbocation is :

(1) three (2) five (3) eight (4) six

ANSWER KEY [EXERCISE-III]

Que. 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15
Ans. 1 3 4 2 2 3 1 3 2 2 2 4 4 1 1
Que. 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30
Ans. 4 2 3 1 3 2 4 2 2 3 2 3 2 3 1
Que. 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45
Ans. 3 3 2 4 2 3 3 1 1 2 2 2 4 2 4

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