ORGANIC CHEMISTRY

ELECTRONIC DISPLACEMENT
EFFECTS

CONTENTS
Exercise-I : 2 - 11
Exercise-II : 12 - 19
Exercise-III : 20 - 21
VIBRANT ACADEMY Exercise-IV : 22 - 30
Answer Key : 31 - 33

unacademy

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 EXERCISE - I
INDUCTIVE EFFECT
1. Select correct statement about  effect?
(A)  effect transfers electrons from one carbon atom to another
(B)  effect is the polarisation of  bond electrons
(C)  effect creates net charge in the molecule
(D)  effect is distance independent

2. CH2 = CH – CN
3 2 1
C1-C2 bond of this molecule is formed by
(A) sp3-sp2 overlap (B) sp2-sp3 overlap (C) sp-sp2 overlap (D) sp2-sp2 overlap

3. Which of the carbocation is most stable?

   
(A) CH3 – CH2 (B) CH3 (C) CH2  CH (D) HC  C

4. List the following carbocations in order of decreasing stability (starting with the most stable)

VIBRANT ACADEMY + +
+
+

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

(A) ii, iii, i, iv (B) iii, iv, ii, i (C) iii, iv, i, ii (D) i, ii, iv, iii

5. Which is the correct stablity order?

unacademy
   
(A) CH 3CH 2CH 2CH 2 > CH 3CHCH 2CH3> (CH 3)2CCH 2CH 3 > (CH 3) 3C

(B) CH3CH2CH2CH2 > CH3CHCH2CH3 > (CH3)2CCH2CH3 > (CH3)3C

(C) CH3CH2CH2CH2> CH3CHCH2CH3 > (CH3)2CCH2CH3

(D) None of these

RESONANCE
6. In which of the following molecules resonance takes place through out the entire system.

COOCH3
(A) (B) (C) (D) |
COOCH3

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7. In which of the following molecules, all atoms are not coplanar?

(A) (B)

(C) (D)

 –
O
8. (I) CH3 – CH = O (II) CH2 = CH – OH (III) CH – C H – O
3

Among, these, which are canonical structures?

(A) I and II (B) I and III (C) II and III (D) all

9.

VIBRANT ACADEMY
Among these canonical structures, the correct order of stability is
(A) I > II > III (B) III > II > I (C) I > III > II (D) II > I > III

10. I CH2 = CH – CH = CH – OCH3

–
O O
II CH2 – CH = CH – CH = OCH3

–
O O
III CH2 = CH – CH – CH – OCH3

IV
unacademy
O –
O
CH2 = CH – CH – CH – OCH3

Among these canonical structures which one is least stable?

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

 –
O
11. (I) CH3–O–CH=CH–CH=CH2 (II) CH3  O  CH  CH  CH  CH2

 –
O
(III) CH3  O  CH  CH  CH2  CH2

Among these three canonical structures (through more are possible) what would be their relative contribution
in the hybrid :
(A) I > II > III (B) III > II > I (C) I > III > II (D) III > I > II

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12. The most stable resonating structure of following compound is

(A) (B)

(C) (D)

13.

Among these canonical structures of pyridine, the correct order of stability is

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

14.VIBRANT ACADEMY
The least stable canonical structure among these is
(A) I (B) II (C) III (D) all are equally stable

15.

unacademy
Which of the following compounds has maximum electron density in ring?

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

16. CH3COOH CH3COONa CH3CONH2

I II III
Among these compounds, the correct order of resonance energy is
(A) I > II > III (B) III > II > I (C) II > III > I (D) II > I > III

17.

Among these compounds, which one has maximum resonance energy?

(A) I (B) II (C) III (D) IV
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18. In which of the following molecules resonance structures are equivalent :

(A) HCOO (B) CH2=CH–CH=CH2 (C) (D)

19. HCNO (isocyanic acid) has following resonating structures :

   
HN  C  O  H  N – C  O  H  N  C – O
  

The order of stability is :

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

20. In which delocalisation of positive charge is possible

+ +
NH3 H H OH2 O¯
N +
(A) (B) + (C) (D)

21. Stability order of the following species?

VIBRANT ACADEMY O
NH
C

S

O
NH
C

S

O
NH
C

S

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

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

CH2 CH2

unacademy
CH2
CH2
NO2 CN CN

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

NO2 NO2
NO2 CN NO2

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

AROMATIC

23.
–
O O
I II III

Which of these cyclopropene systems is aromatic?

(A) I (B) II (C) III (D) all of these

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24. Which of the following compounds is not aromatic?

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

25. 2SbCl5
   
P will be

(A) (B) (C) (D) mixture of (a) and (b)

26.

The aromatic character is maximum in which of these three compounds?

27.VIBRANT ACADEMY
(A) I (B) II (C) III

Select the correct statement regarding the following compounds :

(D) same in all

(I) (II)

(A) II has greater dipole moment than I (B) Covalent characters of II is less than I
(C) I is more soluble in polar solvent than II (D) None of these
28. Arrange the following carbocations in decreasing order their stability?

(I)
unacademy(II)
CH3

(III) (IV)
CH3 CH3

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

HYPERCONJUGATION

29. Which of the following has most negative heat of hydrogenation?

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

30. The hyperconjugative stabilities of tert-butyl cation and 2-butene respectively are due to :
(A) (filled)  p(empty) and (filled)  * (empty) electron delocalisation
(B) (filled)  p(empty) and (filled)  (empty) electron delocalisation
(C) (filled)  p(filled) and (filled)  * (empty) electron delocalisation
(D) p (filled)  *(empty) and (filled)  (empty) electron delocalisation
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31. The compound having all resonance, inductive and hyper-conjugation effect is :
H3C H H
(A) C = CH2 (B) C = CH2 (C) C=O (D) H2C = CH – CH = CH2
H3CO H3CO H 3CO

32. Arrange the following carbocations in the increasing order of their stability.

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

33. Which of the following is most stable carbocation :

CH CH C CH3
(A) CH2 C CH3 (B)
CH3
CH3
CH2CH3

CH3 C
(C) CH 3 CH2 CH (D)

VIBRANT ACADEMY
34. How many hyper conjugative hydrogen atoms are in

(A) 3 (B) 4 (C) 0 (D) 5

35.

unacademy
What is the correct order of stability of given free radical

CH2
•

CH3
•
CH2
•
CH2

CH3
CH3
(1) (2) (3)

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

36. Correct order of heat of combustion is

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

(A) 3 > 2 > 4 > 1 (B) 2 > 1 > 3 > 4 (C) 4 > 3 > 2 > 1 (D) 1 > 2 > 3 > 4
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37. The correct stability orders of following alkenes is
CH3

CH3
(1) (2) (3) (4)
(A) 1 > 2 > 3 > 4 (B) 3 > 4 > 2 > 1 (C) 2 > 4 > 3 > 1 (D) 4 > 3 > 2 > 1

38.
(I) (II) (III)
HOC order is
(A) II > I > III (B) III > I > II (C) III > II > I (D) None of these

39. Which of the following alkenes will show maximum number of hyperconjugation forms?

CH3
|
(A) CH2 = CH2 (B) CH3 – CH = CH2 (C) CH3 – CH2 – CH = CH2 (D) CH3– CH – CH = CH2

40. Hyperconjugation observed in

VIBRANT ACADEMY
(A)
• •
(B) CPh3 (C)
•
Me
Me
(D)
•

41. Write correct order of stability of following carbocations:

ACID :
(A) I > II > III > IV unacademy
(B) III > II > I > IV (C) III > I > II > IV (D) III > II > IV > I

42. Rank the following compounds in order of decreasing acidity of the indicated hydrogen :
O O O O O O
|| || || || || ||
CH3CCH2CH2CCH3 CH3CCH2CH2CH2CCH3 CH3CCH2CCH3

(I) (II) (III)

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

43. Which of the following will accept H+ from NH4+ ion ?

NH2

(A) (B) (C) N (D) CH3 – CH2 – NH2

NH2 H
CH3
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44. The strongest acid among all isomers is
COOH
COOH COOH Br COOH
Br Cl Br
(A) (B) (C) (D)
Cl Br Cl
Cl

45. Which of the following is not correct decreasing ka order

(A) CH4 > NH3 > H2O > HF
(B) CH3OH > CH3NH2 > CH3–F > CH3–CH3
(C) HI > HBr > HCl > HF
(D) PhOH > H2O > C2H5OH > CH3–C  CH

46. Find the strongest acid among the following compounds is :

(A) HOOC – (CH2)2 – COOH (B) H3N+ – (CH2)2 – COOH
(C) F – (CH2)2 – COOH (D) CH3 – (CH2)2 – COOH

47. Find the correct order of ka of following compounds

COOH
COOH COOH COOH COOH
NO2
(I) (II) (III) (IV) (V)

48.
VIBRANT ACADEMY OCH3
(A) I < II < III < IV < V (B) IV < I < III < II < V
NO2
(C) III < II < I < IV < V

The correct order of acidic strength of the following compounds is

NO2
(D) II < I < III < IV < V

COOH

COOH
COOH

O
(I) (II) (III)

(A) II > III > I

unacademy
(B) II > I > III
OH

(C) I > II > III (D) II > I = III

49. Arrange the following in increasing order of their acidic strength

O O
O O O
C
OCH3
(I) (II) O (III) (IV)
O O O
(A) III < I < IV < II (B) II < I < IV < III (C) I < III < IV < II (D) II < III < I < IV

50. Identify correct acidic strength order in the following compounds

H
H H
O N O
N O O N O
(I) (II) (III)
N
H
(A) I > II > III (B) II > III > I (C) I > III > II (D) III > I > II

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51. Identify correct acidic strength order in the following compounds
H H H

(I) O O (II) O S (III) S S

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

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

HN NH2 HN NH2 HN NH2

HN NH2 C C C
C

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

NH2 NO2 Cl

(A) ii > iv > i > iii (B) iii > i > iv > ii (C) iii > iv > i > ii (D) ii > i > iv > iii
53. Correct basic strength order is :
NH2 NH2 NH Et NH2
Et NO2
(p) (q) (r) (s)

54.
VIBRANT ACADEMY
(A) r > q > p > s (B) r > p > q > s

Find the order of basic strength. (if R = Me)?

(C) q > r > p > s (D) r > q > s > p

(A) R4N+ (B) R3N (C) R2NH (D) RNH2

55. In the labelled N–atoms which is correct basic strength order :

H
(1) ••
N
••
NH
(2)

unacademy O
••
N
H
(3) O

(A) 2 > 1 > 3 (B) 3 > 1 > 2 (C) 2 > 3 > 1 (D) All are equally basic

56. Which is the weakest base among the following?

CH3
CH3
(A) (B) (C) (D)
CH3 N N CH3 N CH3
N

MIXED QUESTIONS

57. Which of the following has longest C – O bond :

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

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58. CH2 = NH

I II III IV
Among these compounds, the correct order of C – N bond lengths is :
(A) IV > I > II > III (B) III > I > II > IV (C) III > II > I > IV (D) III > I > IV > II

59. Which one of the following carbonyl compound when treated with dilute acid forms the more stable carbocation?

O O
|| ||
(A) CH 3  C  CH 3 (B) (C) (D) C6 H 5  C  C 6 H 5

60. Correct order of rate of hydrolysis or rate of reaction toward AgNO3 for following compounds is

[I] [II] [III] [IV]

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

61. The abstraction of proton will be fastest, in which carbon in the following compound

62.
(A) x

unacademy
(B) y (C) z

Among the following molecules, the correct order of C – C bond lenght is

(A) C2H6 > C2H4 > C6H6 > C2H2
(D) p

(B) C2H6 > C6H6 > C2H4 > C2H2(C6H6 is benzene)

(C) C2H4 > C2H6 > C2H2 > C6H6 (D) C2H6 > C2H4 > C2H2 > C6H6

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

CH3

CH3
 II  IV
(A) II > I > IV > III (B) III > I > II > IV (C) IV > II > I > III (D) IV > I > II > III
64. Which of the following has shortest C–Cl bond?
Cl

(A) CH3Cl (B) CH2 = CH – Cl (C) (D) CH2 = CH – CH = CH – Cl

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 EXERCISE - II
1. In which of the following molecules resonance takes place through out the entire system.
NH2 CH2NH2

(A) CH3CH2NHCH2CH = CH2 (B) (C)


CH2

(D) CH2 = CHCH2CH=CH2 (E) (F)

CH3
| +
(G) (H) CH3CCH2CH=CH2 (I)
+

2. Which of the following pairs of structures are resonance contributors?

O O
|| ||
(A) and  HCH  CH and CH C
(B) CH3 CH  CHC 
2 3 HCH  CHCH  CH2

VIBRANT ACADEMY
O
||
OH
|
(C) CH3CCH2CH3 and CH3C=CHCH3 (D) and
+

+
 
(E) CH3 C HCH  CHCH3 and CH3 CH  CHCH2 C H2

3. In each of the following pairs of ions which ion is more stable:

unacademy
   
(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
 

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4. Draw the resonance forms to show the delocalization of charges in the following ions
O O
+
–
O –
O CH2
(a) CH3 – C – CH2 (b) H – C – CH = CH – CH2 (c)
+

(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 (k)

(l) (m) (n)

5. Draw a second resonance structure and the hybrid for each species, and then rank the two resonance
structures and the hybrid in order of increasing stability.

6.
VIBRANT ACADEMY
(A) (B)

For acetic acid (CH3CO2H): (a) Draw three resonance structures; (b) draw a structure for the resonance
hybrid; (c) rank the three resonance structures and the resonance hybrid in order of increasing energy.

7. Use resonance theory to explain why both C – O bond lengths are equal in the acetate anion.

8.
unacademy
In the following sets of resonance forms, label the major and minor contributors and state which structures
would be of equal energy. Add any missing resonance forms.

(a) CH3—CH–CN CH3—CH=CN

O¯ O¯
(b) +
CH3—C=CH–CH—CH3 CH3—C—CH=CH—CH3
+

O O O¯ O
(c)
CH3—C–CH–C—CH3 CH3—C=CH–C—CH3

(d) [CH3  C H  CH  CH  NO 2 
 CH3  CH  CH  C H  NO 2 ]

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 NH2 NH2
(e) +
CH3—CH2—C—NH2 CH3—CH2—C = NH2
+
9. From each set of resonance structure that follow, designate the one that would contribute most to the hybrid
and explain your choice.
CH 3 CH 3
| |
(a) CH 3CH 2C  CH  CH 
2 CH 3CH 2 C CH  CH 2

(i) (ii)

 •• 
(b) (c) C H 2  N(CH 3 ) 2 CH 2  N(CH 3 ) 2
(i) (ii) (i) (ii)

(d) (e) : NH2 – C  N:

(i) (ii) (i) (ii)

10. Identify more stable canonical structure in each of the following pairs :

VIBRANT ACADEMY
(a)
H
O
C ..
OH H
O
C 
OH
(b) (c)

 
(d) C H  CH  CH  O 
 CH 2  CH  CH  O (e)
2

11. Which of the following pairs has higher resonance energy :

unacademy

(a) CH3COOH and CH3COONa (b) CH2 = CH – O and CH2 = CH – OH

(c) and (d) and

(e) and CH2 = CH – CH = CH – CH = CH2

12. Which of the following pairs has less resonance energy :

(a) and (b) and

(c) and (d) and

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

(i) (ii) (iii)

14. Rank the following sets of intermediates in increasing order of their stability giving appropriate reasons for
your choice.

(a) C6 H 5 , p  NO 2 (C6 H 4 )  , p  CH 3  (C6 H 4 )  , p  Cl  C 6 H 4

(b)

(A)

15. Which is more acidic and why?

(A) (B)

16.
VIBRANT ACADEMY
Squaric acid is a diprotic acid with both protons being more acidic than acetic acid. In the

di-anion after the loss of both protons all of the C-C bonds are the same length as well as all of the C-O
bonds. Provide a explanation for these observations.

17. Choose the more stable alkene in each of the following pairs. Explain your reasoning.
(a) 1-Methylcyclohexene or 3-methylcyclohexene
(b) Isopropenylcyclopentane or allylcyclopentane

18. Consider the given reaction:

unacademy
+ 3H2 Pd
 /C


In the above reaction which one of the given ring will undergo reduction?

19. Compare heat of hydrogenation (Decreasing order)

(a) and

(b) and

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(c) and

20. (I) Stability order and (II) heat of hydrogenation orders.

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

(B) (i) (ii) (iii)

21. 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

22. Write stability order of following intermediates:

CH 3
  |

VIBRANT ACADEMY
(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)

unacademy

CH 3
  |
(iv) (a) CH 3  CH 2 (b) CH 3  CH  CH 3 (c) CH 3  C 
|
CH 3

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

(vi) (a) (b) (c)

CH 3
–
O –
O |–
O
(vii) (a) CH 3  CH 2 (b) CH 3  CH  CH 3 (c) CH 3  C
|
CH 3

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 –
O

–
O –
O
(viii) (a) (b) (c)

–
O
–
O
(ix) (a) (b) (c)
–
O

–
O –
O –
O
(x) (a) HC  C (b) CH2  CH (c) CH3  CH2
  
(xi) (a) HC  C (b) CH 2  CH (c) CH 3  CH 2

23. Write stability order of following intermediates:

 
CH2 
CH2 CH2

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

N OMe
O O

VIBRANT ACADEMY
–
O
–
O CH2 –
O
CH2 CH2 –
O
CH2
(ii) (a) (b) (c) (d)
N
Cl O O CN

 
CH2 CH2
CH2
OH

unacademy
(iii) (a) (b) (c)
OH
OH

–
O –
O
CH2 CH2

(iv) (a) (b)

F Cl

CH2 CH2–CH2

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

(vi) (a) (b) (c)

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(vii) (a) (b)

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

(ix) (a) (b) (c)

 
CH2 CH2 CH2


H
(x) (a) (b) H (c) C H
C H H
H
H C H
H

CH
2 CH CH2 CH2
2

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

CH3 CH2Me CH Me2 CMe3

24.

(i)
VIBRANT ACADEMY
Write increasing order of heat of hydrogenation :

(a) (b)

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

(iii) (a) (b) (c) (d) (e)

(iv) (a)
unacademy
(b) (c)

(v) (a) (b) (vi) (a) (b)

25. Give decreasing order of heat of combustion (HOC):

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

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

(iii) (a) (b)

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

26. Arrange in order of C–H bond energy

27. (A) Which compound has the greater electron density on its nitrogen atom?

N or N
H H
(B) Which compound has the greater electron density on its oxygen atom?
O O
|| ||
—NHCCH3 or —NHCCH3

28.

VIBRANT ACADEMY
Which of the following acid react with NaHCO3 and liberate CO2(g)?

(i) CCl3 – COOH (ii) CH3 – CH2 – OH (iii)

COOH
CCl3
(iv) HCl

OH OH
COOH NO2 OH
NO2
CMe3
(v) (vi) (vii) (viii)

unacademy
NO2
SO3H NO2

29. Which of the following statement is incorrect about resonance ?

(A) The most stable structure explains all the characteristics of a species.
(B) All resonating structures remain in equilibrium.
(C) Resonance hybrid has maximum similarity with most stable resonating structure.
(D) Resonance hybrid is real.

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 EXERCISE - III
1. Match the Column :
Column I Column II

(A) (P) Six  electrons


(B) (Q) Four  electrons


NH
(C) N  (R) Aromatic compound
H

H–N
(D) (S) Anti-aromatic compound

2.
VIBRANT ACADEMY
Match the Column :
Column I Column II
..
(A) NH (P) Non aromatic

+
(B) (Q) Anti aromatic

(C)
O
unacademy (R) Resonance

(D) (S) Aromatic

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3. Column-I Column-II

(P) (1) Aliphatic Hydrocarbon

(Q) (2) Anti aromatic

(R) (3) Aromatic

O

(S) (4) Alicyclic Compound

Code :
P Q R S P Q R S
(A) 3 1 4 2 (B) 1 2 4 3
(C) 2 1 3 4 (D) 3 2 1 4

VIBRANT ACADEMY

unacademy

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 EXERCISE - IV
Single Choice Questions :
1. The bond between carbon atom (1) and carbon atom (2) in compound

N  C– C H  C H2
1 2 3

involves the hybridisation as [JEE-1987]

(A) sp2 and sp2 (B) sp3 and sp (C) sp and sp2 (D) sp and sp

2. Polarisation of electrons in acrolein may be written as [JEE-1988]

– + – + – +  –
(A) CH2 = CH – C = O (B) CH2 = CH – CH = O (C) CH 2 = CH – CH = O (D) CH 2 = CH – CH = O

3. The compound in which C uses its sp3-hybrid orbitals for bond formation is [JEE-1989]
(A) HCOOH (B) (H2N)2CO (C) (CH3)3COH (D) CH3CHO

4. The number of sigma and pi-bonds in 1-butene 3-yne are [JEE-1989]

(A) 5 sigma and 5 pi (B) 7 sigma and 3 pi (C) 8 sigma and 2 pi (D) 6 sigma and 4 pi

5. The hybridisation of carbon atoms in C — C single bond of H — C  C — CH = CH2 is [JEE-1991]

(A) sp3 – sp3 (B) sp2 – sp3 (C) sp – sp2 (D) sp3 – sp

   
6.

VIBRANT ACADEMY
Which is the decreasing order of strength of the bases OH , NH2 , H—C  C and CH3 — CH2 ? [JEE-1993]
(A) CH3 — CH2– > NH2– > H — C  C– > OH–
(C) OH– > NH2– > H — C  C– > CH3 — CH2–
(B) H — C  C– > CH3 — CH2– > NH2– > OH–
(D) NH2– > H — C  C– > OH– > CH3 — CH2–

7. Choose the correct statement from the ones given below for anilinium ion [JEE-1993]

+
NH3 NH3

unacademy (I) (II)

(A) II is not an acceptable canonical structure because carbonium ions are less stable than ammonium ions
(B) II is not an acceptable canonical structure because it is non aromatic
(C) II is not an acceptable canonical structure because the nitrogen has 10 valence electrons
(D) II is an acceptable canonical structure

8. Most stable carbonium ion is [JEE-1995]

(A) p-NO2 – C6H4 – +CH 2 (B) C6H5+CH2
(C) p-Cl – C6H4 – +CH 2 (D) p-CH3O – C6H4 – +CH2

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9. In the following compounds [JEE-1996]

OH OH OH OH

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

The order of acidity is

(A) III > IV > I > II (B) I > IV > III > II (C) II > I > III > IV (D) IV > III > I > II
10. In the following compounds, the order of basicity is [JEE-1997]
O

N N N N

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

11.
VIBRANT ACADEMY
Among the following compounds, the strongest acid is
(A) HC  CH (B) C6H6 (C) C2H6 (D) CH3OH
[JEE-1998]

12. The most unlikely representation of resonance structure of p-nitrophenoxide ion is [JEE-1999]

O–N=O O–N–O O=N=O O–N=O

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

13.
O
unacademy O
Which of the following has the most acidic hydrogen :
(A) 3-hexanone (B) 2, 4-hexanedione
O

(C) 2, 5-hexanedione
O

(D) 2, 3-hexanedione
[JEE-2000]

14. Amongst the following, the most basic compound is [JEE-2000]

(A) C6H5NH2 (B) p-NO2 – C6H4NH2 (C) m-NO2 – C6H4NH2 (D) C6H5CH2NH2

15. The correct order of basicities of the following compounds is [JEE-2001]

NH2 O
||
(i) CH3 — C (ii) CH3 CH2NH2 (iii) (CH3)2NH (iv) CH 3CNH 2
NH2

(A) ii > i > iii > iv (B) i > iii > ii > iv (C) iii > i > ii > iv (D) i > ii > iii > iv

16. Which of the following hydrocarbons has the lowest dipole moment? [JEE-2002]
(A) cis-2-butene (B) 2-butyne (C) 1-butyne (D) H2C = CH — C  CH

17. Which of the following acids has the smallest dissociation constant? [JEE-2002]
(A) CH3CHFCOOH (B) FCH2CH2COOH (C) BrCH2CH2COOH (D) CH3CHBrCOOH
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18. Which of the following represent the given mode of hybridisation sp2 – sp2 – sp – sp from left to right?
(A) CH2 = CH – C  CH (B) HC  C – C  CH [JEE-2003]
CH2
(C) H2C = C = C = CH2 (D) H2C

OH
CO OH

NO2
2 mole of NaNH 2
19. product (A). The product A will be : [JEE-2003]
CH

OH
  
OOC OH OOC O

NO2
(A) (B)

VIBRANT ACADEMY

CH C

O OH

HOOC  HOOC OH
O

NO2 NO2
(C)
unacademy
CH
(D)


..
C

O O

 
H3N NH3
20. z y

COOH
x
Correct order of acidic strength is [JEE-2004]
(A) x > y > z (B) z > y > x (C) y > z > x (D) x > z > Y

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 SO3H

CH COONa( excess )
3  
21.    [JEE-2005]
(aq. solution)

Me

SO3COOCH3 SO3Na COONa

(A) (B) (C) (D) + H2SO3

Me

Me Me

22. For 1-methoxy-1,3-butadiene, which of the following resonating structure is the least stable ?
   
(A) H2 C– C H – CH  CH – O – CH3 (B) H2 C– CH  CH – CH  O – CH3 [JEE-2005]

VIBRANT ACADEMY
   
(C) H2C  CH – C H – C H – O – CH3 (D) H2C  CH – C H – CH  O – CH3

23. Among the following, the least stable resonance structure is [JEE-2007]

+ – – –
+ O + O + O (D) + O
(A) N (B) N (C) N N
– + + +
O O O O
– – – –
24. Hyperconjugation involves overlap of the following orbitals [JEE-2008]

unacademy
(A)  –  (B)  – p (C) p – p (D)  – 

25. The correct stability order for the following species is [JEE-2008]

  
O O 
(I) (II) (III) (IV)

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

26. The correct acidity order of the following is [JEE-2009]

OH OH COOH COOH

Cl CH3
(I) (II) (III) (IV)
(A) (III) > (IV) > (II) > (I) (B) (IV) > (III) > (I) > (II)
(C) (III) > (II) > (I) > (IV) (D) (II) > (III) > (IV) > (I)

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27. The correct stability order of the following resonance structures is [JEE-2009]
+ – + – – + – +
H 2C = N = N H2 C – N = N H 2C – N  N H2 C – N = N
(I) (II) (III) (IV)

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

28. Among the following compounds, the most acidic is : [JEE-2011]

(A) p-nitrophenol (B) p-hydroxybenzoic acid (C) o-hydroxybenzoic acid (D) p-toluic acid

29. A solution of (–) – 1 – chloro – 1 – phenylethane is toluene racemises slowly in the presence of a small
amount of SbCl5, due to the formation of : [JEE-Mains-2013]
(A) free radical (B) carbanion (C) carbene (D) carbocation

30. Arrange the following compounds in order of decreasing acidity : [JEE-Mains-2013]

OH OH OH OH

; ; ;

Cl CH3 NO2 OCH3

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

31.
VIBRANT ACADEMY
(A) IV > III > I > II (B) II > IV > III > IV

The order of stability of the following carbocations

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

[JEE-Mains-2013]

CH2
 
CH2 = CH – CH2 ; CH3 – CH2 – CH2 ;
I II
III

32.
is
(A) III > I > II
unacademy
(B) III > II > I
Which one of the following is most stable ?
(C) II > III > I (D) I > II > III
[JEE-Mains-Online : 2013]

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

Ph
Ph

33. The order of basicity of amines in gaseous state is : [JEE-Mains-Online : 2013]

(A) 3° > 2° > NH3 > 1° (B) 1° > 2° > 3° > NH3 (C) 3° > 2° > 1° > NH3 (D) NH3 > 1° > 2° > 3°

34. Considering the basic strength of amines in aqueous solution, which one has the smallest pKb value?
(A) CH3NH2 (B) (CH3)3N (C) C6H5NH2 (D) (CH3)2NH [JEE Mains 2014]

35. Among the following oxoacids, the correct decreasing order of acid strength is [JEE Mains 2014]
(A) HClO4 > HOCl > HClO2 > HClO3 (B) HClO4 > HCIO3 > HClO2 > HOCl
(C) HClO2 > HClO4 > HClO3 > HOCl (D) HOCl > HClO2 > HClO3 > HClO4
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36. In which of the following pairs A is more stable than B ? [JEE Mains Online 2014]
A B A B

(A) (B)

(C) (D) Ph3C , (CH3 )3 C

37. Which one of the following statements is not correct ? [JEE Mains Online 2014]
(A) Alcohols are weaker acids than water.
(B) Acid strength of alcohol decreases in the following order.
RCH2OH > R2CHOH > R3COH
(C) Carbon-oxygen bond length in methanol, CH3OH is shorter than that of C – O bond length in phenol.
O
(D) The bond angle in methanol is 108.9º.
C H

38. Which of the following molecules has two sigma() and two pi() bonds ? [JEE Mains Online 2014]
(A) C2H4 (B) N2F2 (C) C2H2Cl2 (D) HCN

39. Arrange the following amines in the order of increasing basicity (JEE MAIN 2015)

VIBRANT ACADEMYNH2 NH2 NH2 NH2 NH2 NH2

(A) < < < CH3NH2 (B) < < < CH3NH2

OCH3 NO2 OCH3 NO2

unacademy
NH2 NH2 NH2
NH2 NH2 NH2

< < < CH3NH2

(C) CH3NH2 < < < (D)

NO2 OCH3
OCH3 NO2
40. The correct order of acidity for the following compounds is : [IIT-JEE Advance 2016]
CO2H CO2H CO2H CO2H
HO OH OH

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

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41. The IUPAC name of the following compound is : [JEE-Mains Online -2017]

(A) 2-Ethyl-1,1-dimethylcyclohexane (B) 1-Ethyl-2,2-dimethylcyclohexane

(C) 1,1-Dimethyl-2-ethylcyclohexane (D) 2,2-Dimethyl-1-ethylcyclohexane

42. A mixture containing the following four compounds is extracted with 1M HCl. The compound that goes to
aqueous layer is : [JEE-Mains Online -2017]
H O
S N O

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

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

43. Which of the following compounds is most reactive to an aqueous solution of sodium carbonate?
[JEE-Mains Online -2017]

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

44.
VIBRANT ACADEMY
In the following structure, the double bonds are marked as I, II, III and IV
II

III
I IV

Geometrical isomerism is not possible at site (s) : [JEE-Mains Online -2017]

(A) III (B) I (C) I and III (D) III and IV

45.

unacademy
The increasing order of the boiling points for the following compounds is :
(I) C2H5OH (II) C2H5Cl (III) C2H5CH3 (IV) C2H5OCH3
[JEE-Mains Online -2017]
(A) (III) < (IV) < (II) < (I) (B) (IV) < (III) < (I) < (II)
(C) (II) < (III) < (IV) < (I) (D) (III) < (II) < (I) < (IV)
46. Which of the following compounds will show highest dipole moment? [JEE-Mains Online -2017]

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

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

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47. Among the following compounds, the increasing order of their basic strength is :
[JEE-Mains Online -2017]

NH2 CH3
(I) (II) (III)
N (IV)
N NH2
H
(A) (I) < (II) < (IV) < (III) (B) (I) < (II) < (III) < (IV)
(C) (II) < (I) < (IV) < (III) (D) (II) < (I) < (III) < (IV)

48. Which of the following molecules is least resonance stabilized? [JEE-Mains-2017]

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

O O

49. The order of basicity among the following compound is : [IIT Advance - 2017]
NH NH2

N NH HN N
H3C NH2 H2N NH
I II III IV
(A) II > I > IV > III (B) IV > II > III > I (C) I > IV > III > II (D) IV > I > II > III

VIBRANT ACADEMY
50. The increasing order of the acidity of the following carboxylic acids is : [IIT Main Online-2018]

CO2H CO2H CO2H CO2H

NO2 OH Cl
(I) (II) (III) (IV)

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

Multiple Choice Questions :

51.
(A) acetic acid
unacademy
Phenol is less acidic than
(B) p-methoxy phenol (C) p-nitrophenol (D) ethanol
[JEE 1986]

52. The molecule(s) that will have dipole moment is/are [JEE-1992]
(A) 2, 2 dimethyl propane (B) trans 2-pentene
(C) cis 3-hexene (D) 2, 2, 3, 3-tetramethyl butane

53. An aromatic molecule will : [JEE-1999]

(A) have 4n electrons (B) have (4n + 2) electrons
(C) be planar (D) be cyclic

54. The IUPAC name(s) of the following compound is(are) [IIT Advance - 2017]

H3C Cl
(A) 1-chloro-4-methylbenzene (B) 4-chlorotoluene
(C) 4-methylchlorobenzene (D) 1-methyl-4-chlorobenzene

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Subjective :
55. The total number of basic groups in the following form of lysine is [JEE-2010]

O
+
NH3 – CH2 – CH2 – CH2 – CH2 – CH – C
–
O
NH2

56. The total number of contributing structure showing hyperconjugation (involving C–H bonds) for the following
carbocation is [JEE-2011]

H3C  CH2CH3

57. The number of resonance structures for N is [IIT-JEE Advance 2015]

OH
NaOH
N

58.
VIBRANT ACADEMY
Among the following, the number of aromatic compound(s) is : [IIT Advance - 2017]





unacademy

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 ANSWER KEY
Exercise - I
1. B 2. C 3. A 4. B 5. C 6. B 7. C
8. B 9. C 10. D 11. C 12. D 13. A 14. B
15. C 16. C 17. C 18. A 19. A 20. D 21. A
22. D 23. C 24. D 25. B 26. A 27. C 28. C
29. A 30. A 31. A 32. A 33. B 34. D 35. A
36. A 37. D 38. A 39. B 40. D 41. B 42. B
43. D 44. B 45. A 46. B 47. D 48. B 49. D
50. B 51. B 52. D 53. B 54. C 55. A 56. D
57. B 58. C 59. C 60. A 61. A 62. B 63. B
64. C

Exercise - II

1. B, E, I 2. B, D 3. (a) I, (b) I, (c) II, (d) II

O¯ O¯
| |
4. (a) CH 3  C  CH 2 (b) H  C  CH  CH  CH 2
+ +
CH2 CH2 CH2 CH2 CH2

VIBRANT ACADEMY
(c)
+

+
+

(d)
+
(e) O¯ O O O

+
(f) NH (g) (h)
O+
–
O

–
O


(k) H C – CH  CH – CH  CH
unacademy 
(i) CH 3  CH  CH  CH  CH  CH  CH 3 (j) CH 3  CH  CH  CH  CH  CH 2

(l)

(m) Me – CH  Cl
2 2

(n)

    
5. (A) Me 2 C  NH2 > Me  C NH2 Me2 C –––
 
N H2
2 –
O

(B) > –
O
NH

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 – –
O OO OO

6. CH3 – C – OH CH3 – C – O – H CH3 – C = OH

I II III
I > III > II
for three R.S. also count least stable R.S. i.e, II
–
O
+
Resonance hybrid CH3 – C – OH

7. Equivalent R.S.  in hybrid both bond lengths are equal.

O O¯
|| | + O¯
8. (a) II, (b) II, (c) II, CH3 – C – CH = C – CH3 (d) II, CH3 – CH = CH – CH = N
+ O¯
NH2
||
(e) II, CH3 – CH 2 – C – NH 2

9. (a) ii, (b) ii, (c) ii, (d) i, (e) i 10. (a) I, (b) I, (c) I, (d) II, (e) II 11. (a) II, (b) I, (c) I, (d) I, (e) I

12. (a) II, (b) II, (c) II, (d) II 13. iii > ii > i 14. (a) ii < iv < i < iii (b) iii < ii < i

VIBRANT ACADEMY
15. A > B
(A after removing H being aromatic  more stable than B.)
One of the R.S. is having both ring aromatic.

16.

17. (a) i , (b) i

unacademy
18. A
R-stablized & intra H-bonding

19. (a) 2 > 1 (b) 2 <1 (c) 1 < 2

[4 Eq. R.S.]

20. (A) (I) iv > iii > ii > i; (II) i > ii > iii > iv (B) (I) iii > ii > i (II) i > ii > iii
21. (a) I, (b) I, (c) II, (d) I

22. (i) c > b > a (ii) c > b > a (iii) b > c > a (iv) c > b > a
(v) c > b > a (vi) b > c > a (vii) a > b > c (viii) a > b > c
(ix) a > c > b (x) a > b > c (xi) c > b > a

23. (i) b > c > a (ii) b > c > a > d (iii) c > a > b (iv) a < b
(v) a > b > c (vi) a > b > c (vii) a > b (viii) c > b > a > d
(ix) a > c > b (x) c > a > b (xi) a > b > c > d

24. (i) b > a (ii) a > b > d > c (iii) a > b > c > d > e (iv) b > c > a
(v) b > a (vi) b > a

25. (i) c > b > a (ii) a > b > c > d (iii) a > b (iv) c > b > a

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26. d<f<b<c<a<e
On the basis of stability of free radical formed after removal of H ]

27. (A) Second; (B) First 28. [i, iii, iv, v, vi, vii] 29. AB

Exercise - III
1. (A) P, R; (B) Q,S; (C) P,R; (D) P,R
2. (A) P, R; (B) P,R; (C) R,S; (D) P,R
3. A

Exercise - IV
1. C 2. D 3. C 4. B 5. C 6. A 7. C
8. D 9. D 10. D 11. D 12. C 13. B 14. D
15. B 16. B 17. C 18. A 19. A 20. D 21. C
22. C 23. A 24. B 25. D 26. A 27. B 28. C
29. D 30. D 31. A 32. C 33. C 34. D 35. B
36. D 37. C 38. D 39. D 40. A 41. A 42. B
43. C 44. B 45. A 46. A 47. D 48. A 49. D
50. D 51. AC 52. BC 53. BCD 54. AB 55. 2 56. 6
57.
VIBRANT ACADEMY
9 58. 5

unacademy

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