®

ORGANIC
CHEMISTRY
JEE (MAIN+ADVANCED)
LEADER COURSE

EXERCISE
Electronic Displacement Effect
English Medium

 ALLEN
® Electronic Displacement Effects

ELECTRONIC DISPLACEMENT EFFECTS

EXERCISE # O-I
1. Which of the following is false order of – I effect ?
+ +
(A) –F > –Cl > –Br > –I (B) –NR3 > –NH3 > –NO2

(C) –F > –OH > –NH2 (D) > –C º CH > –H

GC0001
2. What is the correct order of inductive effect ?
(A) –O– > –CH3 > –CMe3 (B) –CO2– > –O– > CHMe2
(C) –O– > –CH2Me > –D > –H (D) None
GC0002

®
3. Which of the following groups have + I effect :

(A) (B) (C) (D) —CH = CH2

GC0003
4. Which of the following groups have –I effect :
(A) —OH (B) —C—OH (C) —CH3 (D) —OCH3
O
GC0004
5. How many of the following groups have + I effect :
(a) —OH (b) —O1 (c) —NH2 (d)
(e) —COOH (f) —COO1 (g) —Me (h) —OMe
(i) —F (j)
GC0005
6. Which of the following statements is (are) true about resonance.
(a) Resonance is an intramolecular phenomenon.
(b) Resonance involves delocalization of both s and p electrons.
(c) Resonance involves delocalization of p electrons only.
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(d) Resonance decreases potential energy of an acyclic molecule.

(e) Resonance has no effect on the potential energy of a molecule.
(f) Resonance is the only way to increase molecular stability.
(g) Resonance is not the only way to increase molecular stability.
(h) Any resonating molecule is always more stable than any non resonating molecule.
(i) The canonical structure explains all features of a molecule.
(j) The resonance hybrid explains all features of a molecule.
(k) Resonating structures are real and resonance hybrid is imaginary.
(l) Resonance hybrid is real and resonating structures are imaginary.
(m) Resonance hybrid is always more stable than all canonical structures.
GC0006
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7. Which of the following statement is incorrect ?

(A) Resonating structure are real & have real existence
(B) Equivalent contributing structures make resonance hybrid very stable.
(C) Contributing structures are hypothetical having no real existance
(D) Contributing structures are less stable than the resonance hybrid.
GC0007
8. Which of the following is most stable.
(A) Conjugated alkadiene (CH2 = CH—CH = CH2)
(B) Isolated alkadiene (CH2 = CH—CH2—CH = CH2)
(C) Cumulated alkadiene (CH2 = C = CH2)
(D) All are equally stable

®
GC0008
9. Arrange the following resonating structure according to their contribution towards resonance hybrid?
Å 1 1 Å Å 1 1 Å
(a) CH 2 = N = N (b) CH2–N=N (c) CH2–N=N (d) CH2–NºN

(A) a > d > c > b (B) b > a > c > d (C) a > c > b > d (D) d > a > b > c
GC0024
10. A canonical structure will be more stable if
(A) it involves cyclic delocalization of (4n + 2) p – electrons than if it involves acyclic delocalization
of (4n + 2) p – electrons.
(B) it involves cyclic delocalization (4n) p – electrons than if it involves acyclic delocalization of
(4n) p – electrons.
(C) +ve charge is on more electronegative atom than if +ve charge is on less electronegative atom
provided atoms are in the same period.
(D) –ve charge is on more electronegative atom than if –ve charge is on less electronegative atom
provided atoms are in the same period.
GC0010
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11. Which one of the following pair of structures does not represent the phenomenon of resonance?

O O¯
|| + | + +
(A) H 2 C = CH - C - H ; CH 2 - CH = C - H (B) CH 2 = CH - CH Cl ; CH 2 - CH = CH - Cl

O O¯ O O¯
|| | || |
(C) (CH 3 ) 2 CH - C - O ¯ ; (CH 3 ) 2 CH - C = O (D) CH 3 - CH 2 - C - CH 3 ; CH 3 - CH = C - CH 3

GC0011

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12. In which of the following, lone-pair indicated is involved in resonance :

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

··
(e) CH2= CH – C H Q
2 (f) CH2 = CH – CH = N H
GC0012
13. In which of the following lone-pair indicated is not involved in resonance :
· · ··
(a) CH2 = CH – NH – CH3 (b) CH2 = CH – CH = ·O·
··
(c) CH2 = CH – ·O· – CH = CH2 (d) CH2 = CH – C º N ··
CH2

®
(e) (f)
: :
: :

O O
GC0013
14. Which of the following groups cannot participate in resonance with other suitable group :
Å
(a) – COOH (b) –COOCH3 (c) – COCl (d) - NH 3
Å
(e) - C H 2
GC0014
15. Identify electron donating groups in resonance among the following :
(a) – CONH2 (b) – NO2 (c) – OCOCH3 (d) – COOCH3
(e) – CHO (f) – NHCOCH3
GC0015
16. Identify electron withdrawing groups in resonance among the following :
(a) –COOH (b) – CONHCH3 (c) – COCl (d) – CN

(e) – O – CH = CH2 (f)

GC0016
17. Which of the following groups can either donate or withdraw a pair of electrons in resonance depending
node06\B0BC-BD\Kota\JEE(Advanced)\Leader\Chem\Module\3-EDE-Acidic & Basic-Isomerism\Eng\1_EDE\02. Ex.p65

upon situation :
(a) –NO2 (b) – NO (c) – CH = CH2 (d) – CHO
(e) –NH2 (f) – N = NH
GC0017
18. Draw the resonance forms to show the delocalization of charges in the following ions
O
Q
(a) CH3–C–CH 2 GC0018
O
Q
(b) H–C–CH=CH–CH2 GC0018

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+
(c) CH2 GC0018

(d) GC0018
+

(e) O¯ GC0018

(f) + NH GC0019
+

(g) GC0019
O
–

®
(h) GC0019
O
+
(i) CH3 – CH = CH – CH = CH – CH – CH3 GC0019
+
(j) CH3 – CH = CH – CH = CH – CH 2 GC0019
19. Identify less stable canonical structure in each of the following pairs :
Å Å
(a) C H 2 - O - CH 3 ¬
¾® CH 2 = O- CH 3 (b)

(c) (d)

(e)
– +
+ –
CH2 CH2
GC0020
node06\B0BC-BD\Kota\JEE(Advanced)\Leader\Chem\Module\3-EDE-Acidic & Basic-Isomerism\Eng\1_EDE\02. Ex.p65

20. Identify more stable canonical structure in each of the following pairs :
O OQ
1
(a) C .. C Å
(b) O O
H OH H OH
1

(c) (d)

Å Q
(e) C H 2 - CH = CH - O ¬
¾® CH 2 = CH - CH = O (f)

GC0021
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21. Which of the following group can participate in resonance with other suitable group :
(a) –OH GC0022
—
(b) - CH 2 - C H 2 GC0022
Å
(c) - CH - C H2 GC0022
2

(d) GC0022

(e) GC0023

(f) – BH2 GC0023

Å
(g) - P Ph GC0023
3
22. Consider structural formulas A, B and C:
:

:
:
H2C—N N H2C = N = N H2C—N = N
:

®
: :
(A) (B) (C)
(a) Are A, B and C isomers, or are they resonance forms ?
(b) Which structures have a negatively charged carbon?
(c) Which structures have a positively charged carbon?
(d) Which structures have a positively charged nitrogen?
(e) Which structures have a negatively charged nitrogen?
(f) What is the net charge on each structure?
(g) Which is a more stable structure, A or B? Why?
(h) Which is a more stable structure, B or C? Why?
GC0009
23. In each of the following pairs of resonating structure which resonating structure is more stable :

(a) CH3—CH–CºN CH3—CH=C=N

O O O– O
–
(b) CH3 – C – CH – C – CH3 CH3 – C = CH – C – CH3

NH2 NH2
node06\B0BC-BD\Kota\JEE(Advanced)\Leader\Chem\Module\3-EDE-Acidic & Basic-Isomerism\Eng\1_EDE\02. Ex.p65

+
(c) CH3—CH2—C—NH2 CH3—CH2—C = NH2
+

GC0025
24. Formic acid is considered as a hybrid of the four structures
O O1 O
1
OÅ
Å
H– C –OH « H– C = OH « H–C–O–H « H–C–O–H
Å 1

I II III IV
Which of the following order is correct for the stability of four contributing structures.
(A) I > II > III > IV (B) I > II > IV > III (C) I > III > II > IV (D) I > IV > III > II
GC0026
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25. In the given pair of compounds select the one in each pair having lesser resonance energy :

(a) and (b) and

(c) and (d) and

GC0027
26. Resonance energy of resonance hybrid of a molecule will be more if :
(a) canonical structures are equivalent than if canonical structures are non-equivalent
(b) molecule is aromatic than if molecule is not aromatic.

®
GC0028
27. In the given pair of compounds select the one in each pair having higher resonance energy :

(i) and GC0029

(ii) CH2 = CH – O – CH = CH2 and CH2 = CH – NH – CH = CH2 GC0029

Q Q
(iii) CH 2 = CH - N H and HN = CH - N H GC0029
(iv) CH2 = CH – F and CH2 = CH – Br GC0029

CH2
·
(v) and CH2 = CH – C H 2 GC0029

(vi) and GC0029

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(vii) and GC0030

(viii) and GC0030

(ix) CH2 = CH – OH and CH2 = CH – CH = CH – OH GC0030

(x) and GC0030

(xi) CH3COOH and CH3COONa GC0030

Q
(xii) CH2 = CH – O and CH2 = CH – OH GC0030
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(xiii) and GC0030

(xiv) and GC0030

(xv) and CH2 = CH – CH = CH – CH = CH2 GC0030

28. In the given pair of compounds select the one in each pair having lesser resonance energy :

–
(a) CO32– and HCOO– (b) and CH2 = CH – CH2

®
+
(c) and CH2 = CH – CH = CH2 (d) and CH2 = CH – CH2

(e) and

GC0031
29. In which of the following pairs first one is having more resonance energy than the second one -
Å
(A) , (B) Å ,

(C) N , NH2 (D) None of these

H
GC0032
30. In which of the following molecules p – electron density in ring is minimum :
node06\B0BC-BD\Kota\JEE(Advanced)\Leader\Chem\Module\3-EDE-Acidic & Basic-Isomerism\Eng\1_EDE\02. Ex.p65

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

GC0033
31. In which of the following molecules p – electron density in ring is maximum :

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

GC0034
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32. Arrange following compounds in decreasing order of reactivity of ring towards attack of electron deficient
species -

CH3 CH3 H
CH3 H—C—CH3 CH3—C—CH3 H—C—CH 3

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

(A) i > ii > iii > iv (B) iii > iv > ii > i (C) i > iv > ii > iii (D) i > ii > iv > iii
GC0035
33. In which of the following molecule all the effect namely inductive, mesomeric & hyperconjugation operate:

®
(A) —Cl (B) —CH3 (C) —COCH3 (D)

CH3 CH3

GC0036
34. Which one of the following molecules has all the effect, namely inductive, mesomeric and hyperconjugative?
(A) CH3Cl (B) CH3–CH = CH2

(C) CH 3 - CH = CH - C - CH 3 (D) CH2 = CH – CH = CH2

||
O

GC0037

35. Select the correct statement.

(i) Delocalisation of s-electron is hyperconjugation.

(ii) Delocalisation of p-electron is resonance.

(iii) Permanent partial displacement of s-electron is inductive effect.

node06\B0BC-BD\Kota\JEE(Advanced)\Leader\Chem\Module\3-EDE-Acidic & Basic-Isomerism\Eng\1_EDE\02. Ex.p65

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

GC0038

36. Which of the following compound is correctly matched with number of hyperconjugating structures (involving
C—H bond) :

(A) (3) (B) (9) (C) + (8) (D) CH3–CºC–CH3 (5)

GC0039

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37. ¬
¾® ¬
¾®

These are three canonical structures of naphthalene. Examine them and find correct statement among the
following :
(A) All C – C bonds are of same length (B) C1 – C2 bond is shorter than C2 – C3 bond.
(C) C1 – C2 bond is longer than C2 – C3 bond (D) None
GC0040
38. Which of the following has longest C – O bond :

®
(A) (B) (C) (D)

GC0041

39. 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
GC0042
40. C1 – C2 bond is shortest in

2 CH 2
CH 2 2 –C
H3
2 CH
1 C 1 CH 1 C H2 1 C
(A) (B) (C) (D)
node06\B0BC-BD\Kota\JEE(Advanced)\Leader\Chem\Module\3-EDE-Acidic & Basic-Isomerism\Eng\1_EDE\02. Ex.p65

GC0043
41. Which of the following molecule has longest C=C bond length ?
CH3
(A) CH2=C=CH2 (B) CH3–CH=CH2 (C) CH3–C–CH=CH2 (D) CH3–C=CH2
CH3 CH3
GC0044
42. Which of the following molecule has shortest C=C bond length ?
CH3
(A) CH2=C=CH2 (B) CH3–CH=CH2 (C) CH3–C–CH=CH2 (D) CH3–C=CH2
CH3 CH3

GC0045

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43. C—C and C=C bond lengths are unequal in :

(A) Benzene (B) 1,3-buta-di-ene (C) 1,3-cyclohexa-di-ene (D)

GC0046
44. Among the following molecules, the correct order of C – C bond length is (C6H6 is benzene)
(A) C2H6 > C2H4 > C6H6 > C2H2 (B) C2H6>C6H6> C2H4 > C2H2
(C) C2H4 > C2H6 > C2H2 > C6H6 (D) C2H6 > C2H4 > C2H2 > C6H6
GC0047
45. CH3O – CH = CH – NO2 I

CH2 = CH – NO2 II

®
CH2 = CH – Cl III

CH2 = CH2 IV

Which of the following is the correct order of C – C bond lengths among these compounds :

(A) I > II > III > IV (B) IV > III > II > I (C) I > III > II > IV (D) II > III > I > IV
GC0048

46. Which of the following is (are) the correct order of bond lengths :

(A) C – C > C = C > C º C > C º N (B) C = N > C = O > C = C

(C) C = C > C = N > C = O (D) C – C > C = C > C º C > C – H

GC0049

47. In which of the following pairs, indicated bond having less bond dissociation energy :

(a) and CH 2 = CH 2 GC0050

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(b) CH3 - C º CH and HC º CH GC0050

­ ­

(c) and GC0050

(d) and GC0051

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(e) and GC0051

(f) and GC0051

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

(a) CH3 - CH 2 - Br and CH 3 - CH 2 - Cl GC0052
­ ­
(b) CH 3 - CH = CH - Br and CH 3 - CH - CH 3 GC0052

®
­ ®|
Br

(c) and CH3 - CH 2 - Cl GC0052

­
(d) CH 2 = CH - CH = CH 2 and CH 2 = CH 2 - CH 2 - CH3 GC0052
­ ­
(e) CH 2 = CH - CH = CH 2 and CH 2 = CH - NO 2 GC0053
­ ­

(f) and GC0053

H H
2 3 4
49. H3C–C–CH–CH2–H
1
CH2=C–H

the correct order of bond dissociation energy (provided bond undergoes homolytic cleavage):
node06\B0BC-BD\Kota\JEE(Advanced)\Leader\Chem\Module\3-EDE-Acidic & Basic-Isomerism\Eng\1_EDE\02. Ex.p65

(A) C2–H > C3– H > C4 –H > C1 – H (B) C2–H > C3– H > C1 –H > C4 – H

(C) C1–H > C4– H > C2 –H > C3 – H (D) C1–H > C4– H > C3 –H > C2 – H

GC0054

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

(A) (B) (C)

GC0055
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51. In which case, C – O bond length is shorter for Ist compound :

O O
b
C –a OH C –b OH a O HC = O
(A) (B)
CMe3

a b
CH = O CH = O O O

(C) (D)

NH2

GC0056

®
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EXERCISE # O-II
1. In each set of species select the aromatic species.
+
(i) (a) 1 (b) (c)
S
GC0057
+ 1
(ii) (a) (b) (c) 1 (d)

GC0058
+ 1 1 Å
(iii) (a) (b) (c) (d)
Å

®
N
H
GC0059
H
B
(iv) (a) (b) (c) (d)
Si B
H H
B
H–N N–H
(e) (f) GC0060
N–B B–H N
N H
H

2. Which of the given compound is aromatic, antiaromatic or nonaromatic.

H
+
node06\B0BC-BD\Kota\JEE(Advanced)\Leader\Chem\Module\3-EDE-Acidic & Basic-Isomerism\Eng\1_EDE\02. Ex.p65

(a) N (b) N S (c) (d)

O O O
isoxazole 1,3-thiazole pyran pyrylium ion

O NH2

(e) (f) (g) N

O N N O
H
g-pyrone H
1,2-dihydropyridine
cytosine
GC0061

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3. (I) (II) (III)

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

(A) I > II > III (B) I > III > II (C) II > I > III (D) II > III > I
GC0062
4. Which of the given compunds has minimum rotation energy barrier across indicated carbon-carbon
bond.

5.
(A) I (B) II

Which species is not aromatic ?

(C) III

® (D) All are equal

GC0063

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

N N
:

GC0064
6. Which of the following are non-aromatic
node06\B0BC-BD\Kota\JEE(Advanced)\Leader\Chem\Module\3-EDE-Acidic & Basic-Isomerism\Eng\1_EDE\02. Ex.p65

H B
H
N N N
(A) (B) (C) (D)
B B
O N N H N H

GC0065
7. Write down the structure of the following molecule and comment on aromaticity ?
(a) B3H3O3 (b) C3N3 (NH2)3 (c) Trimer of isocyanic acid (HN = C = O)3
GC0066

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8. Select the least stable one :

Å
(A) CH3 – CHÅ2 (B) CH3 – CH2 – CH2

H3 C Å H3C Å
(C) H C CH – CH2 (D) H3C C – CH2
3 H3C
GC0067
9. Write stability in decreasing order of following intermediates:
CH 3
Å Å |
(i) (a) CH 3 - CH 2 (b) CH 3 - CH - CH 3 (c) CH 3 - C Å GC0068
|
CH 3

®
Å
Å Å
(ii) (a) (b) (c) GC0069

Å
(iii) (a) (b) Å (c) GC0070
Å

Å Å
Å Å
(iv) (a) (b) (c) (d) GC0071

+ + +
(v) (a) CF3 - CH 2 (b) CCl3 - CH 2 (c) CBr3 - CH 2 GC0072

(vi) (a) + (b) + (c) + GC0073

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Å Å Å
(vii)(a) HC º C (b) CH 2 = CH (c) CH 3 - CH 2 GC0074

(viii) (a) C6H5+ (b) p–NO2(C6H4)+ (c) p–CH3–(C6H4)+ (d) p–Cl–C6H4+ GC0075

Å Å
CH2 CH2 CH2Å

(ix) (a) (b) (c) GC0076

N OMe
O O

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CH2Å CH2Å CH2Å

OH
(x) (a) (b) (c) GC0077
OH
OH

Å Å Å
CH2 CH2 CH2
H
C H
(xi) (a) (b) H (c) H GC0078
C H
H
H C H
H

®
CHÅ
2 CH2Å CH2Å CH2Å

(xii) (a) (b) (c) (d) GC0079

CH3 CH2Me CH Me2 CMe3

Me Ph Å
| | +
+
(xiii) (a) Me - C + (b) Ph — C (c) Me – CH 2 (d) GC0080
| |
Me Ph

+
+
(xiv)(a) (b)

+
(c) (d)

+
node06\B0BC-BD\Kota\JEE(Advanced)\Leader\Chem\Module\3-EDE-Acidic & Basic-Isomerism\Eng\1_EDE\02. Ex.p65

(e) GC0081
+

+ +
CH2 CH2 +

(xv) (a) (b) (c) GC0082

+ +
+
(xvi) (a) (b) (c) GC0083

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10. Consider the following statements:

Å Å
(I) CH 3O CH 2 is more stable than CH 3 CH 2

Å Å
(II) Me 2 CH is more stable than CH 3CH 2 CH2

Å Å
(III) CH 2 = CH - CH2 is more stable than CH 3 CH 2 CH2

Å Å
(IV) CH 2 = CH is more stable than CH 3 CH 2

Of these statements:
(A) I and II are correct (B) III and IV are correct

®
(C) I, II and III are correct (D) II, III and IV are correct
GC0084
11. In each of the following pairs of ions which ion is more stable:
Å Å Å Å
(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
Å Å
GC0085
12. Find out correct stability order in the following carbocations-
Å Å
Å
(I) (II) (III) (IV)
Å

(A) IV > I > III > II (B) IV > III > I > II (C) I > IV > III > II (D) I > III > IV > II
GC0086
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13. Which of the following carbonium ion is most stable ?

(A) Ph3C+ (B) (CH3)3 C+ (C) (CH3)2 CH+ (D) CH2 CH—CH2+
GC0087
14. Consider the following carbocations
Å Å Å Å
(a) CH3O– –CH2 (b) –CH2 (c) CH3– –CH2 (d) CH3— C H2

The relative stabilities of these carbocations are such that :-

(A) d < b < c < a (B) b < d < c < a (C) d < b < a < c (D) b < d < a < c
GC0088

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Å Å Å Å
CH2 CH2 CH2 CH2

15.

OH NH2 CH3 CH3–C–CH3

CH3

Correct order of carbocation stability is :

(A) 2 > 1 > 4 > 3 (B) 1 > 2 > 4 > 3 (C) 3 > 4 > 2 > 1 (D) 2 > 1 > 3 > 4
GC0089
16. Arrange the following carbocation in the increasing order of stability :
Å Å
CH2 Å
CH2 CH2

®
CH3
CH3–CH CH–CH3
CH3 NO2 CH3 NO2
(I) (II) (III)

(A) I < II < III (B) II < III < I (C) III < II < I (D) III < I < II
GC0090
17. Rank the following sets of intermediates in increasing order of their stability.
1 CH21
CH2

(i) (a) (b) GC0091

F NO2

CH21 CH21 CH21 CH1

2

(ii) (a) (b) (c) (d) GC0092

node06\B0BC-BD\Kota\JEE(Advanced)\Leader\Chem\Module\3-EDE-Acidic & Basic-Isomerism\Eng\1_EDE\02. Ex.p65

Cl N Cº N
O O
1 1
(iii) (a) CH 2 - CH (b) CH 2 - CH 3 GC0093
||
O

O O O
(iv) (a) (b) (c) 1
GC0094
1 1

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—
CH2 CH2 CH2

(v) (a) (b) (c) GC0095

Cl NO2

1 1 1
(vi) (a) (b) (c) GC0096

CH2 CH2–CH2

®
(vii) (a) (b) (c) GC0097

(viii) (a) (b) (c) GC0098

(ix) (a) (b) GC0099

· ·
(x) (a) CH 2 = CH (b) CH 2 = CH - CH 2 (c) CH2 (d) CH3 GC0100

18. Most stable carbanion is :-

(A) HC C1 (B) C6H51 (C) (CH3)3C—CH21 (D) (CH3)2C CH1

GC0101
19. Most stable carbanion is :
1
CH2
1
CH2
1
(A) CH 13 (B) CH 2 = CH – CH 2 (C) (D)
node06\B0BC-BD\Kota\JEE(Advanced)\Leader\Chem\Module\3-EDE-Acidic & Basic-Isomerism\Eng\1_EDE\02. Ex.p65

NO2
GC0102
20. Identify the most stable anion.

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

GC0103

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21. Correct order of stability :

CH3
+
+ +
(A) > H3C CH3 > CH2–OCH3 > CH3
+
(B) > >

– – – –
CH2–CH2 CH2 CH2 CH2

(C) > > >

NO2 Br CH3
CH3

®
• • • •
(D) CH2 =CH–C > CH2=CH–CH2 > CH3–CH2 >CH2=CH
CH3
GC0104
22. Rank the following sets of intermediates in increasing order of their stability giving appropriate reasons
for your choice.
+ + +
+ O O O
(a) +
O O O
O O O O
(b) CH2—C—CH3 , CH2—C—H , CH2—C—NH2 , CH2—C—OCH3

GC0105
23. Select the correct order of stability of carbon free radicals :
· ·
I. Ph– C H2 II. Ph– C H–CH2–CH3
·
III. Ph– C H–CH=CH2 IV. Ph–C–CH=CH2
CH3
node06\B0BC-BD\Kota\JEE(Advanced)\Leader\Chem\Module\3-EDE-Acidic & Basic-Isomerism\Eng\1_EDE\02. Ex.p65

(A) IV > III > I > II (B) IV > III > II > I (C) I > II > III > IV (D) I > III > II > IV
GC0106
24. CH2 = CH – CH = CH – CH3 is more stable than CH3 – CH = C = CH – CH3 because
(I) (II)

(A) there is resonance in I but not in II (B) there is tautomerism in I but not in II

(C) there is hyperconjugation in I but not in II (D) II has more cononical structures than I.

GC0107

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25. Choose the more stable alkene in each of the following pairs. Explain your reasoning.

(a) 1-Methylcyclohexene or 3-methylcyclohexene

(b) Isopropenylcyclopentane or allylcyclopentane

(c) or

GC0108

26. Match each alkene with the appropriate heat of combustion:

Heats of combustion (kJ/mol) : 5293 ; 4658; 4650; 4638; 4632

®
(a) 1-Heptene (b) 2,4-Dimethyl-1-pentene

(c) 2,4-Dimethyl-2-pentene (d) 4,4-Dimethyl-2-pentene

(e) 2,4,4-Trimethyl-2-pentene
GC0109
27. Stability of :

CH3
(I) CH3–CH=CH–CH3 (II) CH3– C = C – CH3
CH3

(III) CH3– C = CH2 (IV) CH3– C = CH – CH3

CH3 CH3
in the increasing order is :
(A) I < III < IV < II (B) I < II < III < IV
(C) I < IV < III < I (D) II < III < IV < I
node06\B0BC-BD\Kota\JEE(Advanced)\Leader\Chem\Module\3-EDE-Acidic & Basic-Isomerism\Eng\1_EDE\02. Ex.p65

GC0110
28. Which of the following C-H bonds participate in hyperconjugation ?

I IV
H
H CH3
H H
III II

(A) I and II (B) I and IV (C) I and III (D) III and IV
GC0111

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29. Rank the following alkenes in decreasing order of heat of combustion values :

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

(A) II > III > IV > I (B) II > IV > III > I
(C) I > III > IV > II (D) I > IV > III > II
GC0112
30. Write decreasing order of heat of hydrogenation :

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

®
GC0113

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

(e)

GC0114

(iii) (a) (b)

GC0115

(iv) (a) (b) node06\B0BC-BD\Kota\JEE(Advanced)\Leader\Chem\Module\3-EDE-Acidic & Basic-Isomerism\Eng\1_EDE\02. Ex.p65

GC0116

(v) (a) (b)

GC0117
CH3 CH3
(vi) (a) CH2 = CH – CH (b) CH2 = C
CH3 CH2–CH3
GC0118

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31. Write increasing order of heat of hydrogenation :

(i) (a) (b)

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

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

(iv) (a) (b) (c) (HOH per benzene ring)

®
GC0119
32. Give decreasing order of heat of combustion (HOC):

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

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

(iii) (a) (b)

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

GC0120
33. Among the following pairs identify the one which gives higher heat of hydrogenation :

(a) and (b) and

node06\B0BC-BD\Kota\JEE(Advanced)\Leader\Chem\Module\3-EDE-Acidic & Basic-Isomerism\Eng\1_EDE\02. Ex.p65

(c) CH3 – CH = CH – CH3 and CH3 – CH2 – CH = CH2

(d) and

GC0121
34. Arrange the following compounds in order of :
(I) Stability (II) Heat of hydrogenation

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

GC0122

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35. If Heat of hydrogenation of 1-butene is 30 Kcal/mol then heat of hydrogenation of 1,3-butadiene is ?

(A) 30 (B) 60 (C) 57 (D) 25
GC0123
NMe 2 NH 2 SO 3H NO 2 Br

36.
A B C D E

Steric inhibition of resonance takes place :

(A) In A,B only (B) In A, B, C, E (C) C only (D) In A only

GC0124

®
37. Consider the following two structures and choose the correct statements -

O O
:

+ O + O
N N

(I) (II)

(A) carbon-nitrogen bond length structure I is greater than that in structure II

(B) carbon-nitrogen bond length in structure I is less than in structure II

(C) carbon-nitorogen bond length in both structure is same

(D) It can not be compared

GC0125

38. Which of the following statements would be true about this compound :
node06\B0BC-BD\Kota\JEE(Advanced)\Leader\Chem\Module\3-EDE-Acidic & Basic-Isomerism\Eng\1_EDE\02. Ex.p65

(A) All three C – N bonds are of same length.

(B) Cl – N and C3 – N bonds are of same length but shorter than C5 – N bond.

(C) Cl – N and C3 – N bonds are of same length but longer than C5 – N bond.

(D) Cl – N and C3 – N bonds are of different length but both are longer than C5 – N bond
GC0126

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39. Arrange given compounds in decreasing order of dipole moment :
CH3 CH3 CH3
Cl
(i) (a) (b) (c) GC0127
Cl
Cl
NO2 NO2 NO2
Cl
(ii) (a) (b) (c) GC0128
Cl
Cl
NMe2 NMe2

(iii) (a) (b) GC0129

®
Å
40. Why a cation like is not possible.
GC0130
node06\B0BC-BD\Kota\JEE(Advanced)\Leader\Chem\Module\3-EDE-Acidic & Basic-Isomerism\Eng\1_EDE\02. Ex.p65

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EXERCISE # S-I
1. Cyclopentadienyl anion is much more stable than allyl anion because :

(A) Cyclic anion is more stable than acyclic anion

(B) Delocalised anion is more stable than localised anion

(C) Cyclopentadienyl anion is aromatic in nature

(D) None of these

GC0131

2. Select correct statement regarding given compounds :

CH3OCH3 C 2H 5OH

®
I II
(A) Boiling point of II is higher than I
(B) Boiling point of II is lower than I
(C) Compound I forms intramolecular H-bonding
(D) Compound II forms intermolecular H-bonding
GC0132
I II III IV
3. In the compund, CH3—CH=CH—CºN , the most electronegative carbon is :
(A) I (B) II (C) III (D) IV
GC0133

4.
node06\B0BC-BD\Kota\JEE(Advanced)\Leader\Chem\Module\3-EDE-Acidic & Basic-Isomerism\Eng\1_EDE\02. Ex.p65

(I) (II)
Carbocation (I) is more stable than carbocation (II), because :

(A) —CD3 has more + I effect than —CH3 (B) —CH3 has more + I effect than —CD3

(C) —CH3 has more + H effect than —CD3 (D) —CD3 has more + H effect than —CH3

GC0134

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5. Select correct statement :

(A) Carbon-oxygen bonds are of equal length in acetate ion
(B) Resonating structures of acetate ion are equivalent
(C) Carbon-oxygen bonds are of unequal length in formate ion
(D) Resonating structures of formate ion are equivalent
GC0135
6. Match the column I with column II.
Column-I Column-II
(Group attached with benzene ring) (Effect shown by the group)
(A) —NO2 (P) – R effect
(B) —O– (Q) + R effect
(C) —O—CH3 (R) + I effect

®
(D) —C º N (S) – I effect
GC0136
7. Column- I Column- II
(Groups attached to phenyl ring) (Effect shown)
:

(A) —N = O (P) +M

(B) —CH3 (Q) –M

O
:

(C) —NH – C (R) +H

CH3
(D) – C – OCH3 (S) –I
O
GC0137
8. Match the column :
Column-I Column-II
(A) Group donate e– inductively but does not (P) –OH
donate / withdraw by resonance
node06\B0BC-BD\Kota\JEE(Advanced)\Leader\Chem\Module\3-EDE-Acidic & Basic-Isomerism\Eng\1_EDE\02. Ex.p65

(B) Group withdraw e– inductively but does not (Q) –NO2

donate / withdraw by resonance
(C) Group withdraw e– inductively & donate (R) –CH2–CH3
e– by resonance
+
(D) Group withdraw e– inductively & withdraw (S) - N H 3
e– by resonance
(T) –NH2
GC0138

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®

9. Match the column I with column II.

Column-I Column-II

(A) (P) Aromatic

(B) (Q) Non-aromatic

(C) +
(R) Anti-aromatic

(D) (S) Cyclic structure

®
GC0139
10. Statement-I : —C—OEt
a —C—O—C— bond length a < b
b
O O O
Because
Statement-II : More is the double bond character less is the bond legnth.
(A) Statement-1 is true, statement-2 is true and statement-2 is correct explanation for statement-1.
(B) Statement-1 is true, statement-2 is true and statement-2 is NOT the correct explanation for
statement-1.
(C) Statement-1 is true, statement-2 is false.
(D) Statement-1 is false, statement-2 is true.
GC0140
+ + + +
11. Statement-I : Me3 C is more stable than Me2 C H and Me2 CH is more stable than the Me C H2 .
Because
Statement-II : Greater the number of hyperconjugative structures, more is the stability of carbocation.
(A)Statement-1 is true, statement-2 is true and statement-2 is correct explanation for statement-1.
(B) Statement-1 is true, statement-2 is true and statement-2 is NOT the correct explanation for
statement-1.
node06\B0BC-BD\Kota\JEE(Advanced)\Leader\Chem\Module\3-EDE-Acidic & Basic-Isomerism\Eng\1_EDE\02. Ex.p65

(C) Statement-1 is true, statement-2 is false.

(D) Statement-1 is false, statement-2 is true.
GC0141
12. Statement-I : The potential energy barrier for rotation about C = C bond in 2-butene is much higher
than that in ethylene.
Because
Statement-II : Hyperconjugation effect decreases the double bond character.
(A) Statement-1 is true, statement-2 is true and statement-2 is correct explanation for statement-1.
(B) Statement-1 is true, statement-2 is true and statement-2 is NOT the correct explanation for
statement-1
(C) Statement-1 is true, statement-2 is false
(D) Statement-1 is false, statement-2 is true.
GC0142

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®

17. The most stable carbocation among the following :

NO2
Å Å
(A) (B) (C) (D) Å
Å

GC0147
18. In which of the following cases, the carbocation (I) is less stable than the carbocation (II) ?
+ +
CH2 CH2
+ +
(A) C6H5— C H2 (I), CH2= CH— C H2 (II) (B) (I), (II)

+ + + Å
(C) CH2= C H (I), CH3— C H2 (II) (D) H3C— C H2 (I), CH2— CH2 (II)

®
F

GC0148
19. Examine the structures I and II for nitromethane and choose the statement correctly :
•• • •–
+2 O
••

••

O
+
CH3—N • • – CH3—N • • –
O O
••
••

•• ••
(I) (II)

(A) Structure II is unlikely representation because electrons have shifted to oxygen

(B) Structure II is unlikely representation because nitrogen has sextet of electrons
(C) Structure II is acceptable and important
(D) None of these
GC0149
20. Examine the following two structures for pyrrole and choose the correct statement given below node06\B0BC-BD\Kota\JEE(Advanced)\Leader\Chem\Module\3-EDE-Acidic & Basic-Isomerism\Eng\1_EDE\02. Ex.p65

•• ••
N N–
H H
(I) (II)

(A) II is not an acceptable resonating structure because carbonium ions is less stable than nitride ion
(B) II is not an acceptable resonating structure because there is charge separation
(C) II is not an acceptable resonating structure because nitrogen has ten valance electrons
(D) II is an acceptable resonating structure
GC0150

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21. Delocalization of electrons increases molecular stability because :

(A) Potential energy of the molecule decreases (B) Electron-electron repulsion decreases
(C) Both (A) and (B) (D) Electron-electron repulsion increases
GC0151
22. The most stable and the least stable carbocation among
Å

+ + +
(I) (II) CH2=CH— C H2 (III) C6H5— C H2 (IV) CH3 — C H — CH3

are respectively :
(A) II, I (B) III, IV (C) I, II (D) I, IV

®
GC0152
23. Most stable carbocation is formed by the heterolysis of :
(A) (CH3)3CBr (B) (C6H5)3CBr (C) (C6H5)2CHBr (D) C6H5CH2Br

GC0153
24. Total number of aromatic compounds

HO O
(a) (b) (c) (d) Å
N
HO O
H H

(e) (f)

GC0154
25. Identify total number of compounds which are unstable at room temperature ?
node06\B0BC-BD\Kota\JEE(Advanced)\Leader\Chem\Module\3-EDE-Acidic & Basic-Isomerism\Eng\1_EDE\02. Ex.p65

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

H
B
(v) (vi) (vii)

GC0155

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®

EXERCISE # J-MAIN
1. In the following benzyl/allyl system [AIEEE-2002]

R–CH=CH2 or R

(R is alkyl group)
decreasing order of inductive effect is-
(1) (CH3)3C– > (CH3)2CH– > CH3CH2– (2) CH3–CH2– > (CH3)2CH– > (CH3)3C–
(3) (CH3)2CH– > CH3CH2– > (CH3)3CH– (4) None of these

GC0156
2. In the anion HCOO– the two carbon-oxygen bonds are found to be of equal length. What is the

®
reason for it- [AIEEE-2003]
(1) Electronic orbits of carbon atoms are hybridised
(2) The C=O bond is weaker than the C–O bond
(3) The anion HCOO– has two resonating structure
(4) The anion is obtained by removal of a proton form the acid molecule

GC0157
3. Which one of the following does not have sp2 hybridised carbon [AIEEE-2004]
(1) Acetamide (2) Acetic acid
(3) Acetonitrile (4) Acetone

GC0158
4. Due to the presence of an unpaired electron, free radicals are - [AIEEE-2005]
(1) Chemically inactive (2) Chemically reactive
(3) Cations (4) Anions node06\B0BC-BD\Kota\JEE(Advanced)\Leader\Chem\Module\3-EDE-Acidic & Basic-Isomerism\Eng\1_EDE\02. Ex.p65

GC0159
5. The increasing order of stability of the following free radicals is [AIEEE-2006]
· · · ·
(1) (C6 H5 )3 C < (C6 H5 )2 C H < (CH3 )3 C < (CH3 )2 C H
· · · ·
(2) (C6 H5 )2 C H < (C6 H5 )3 C < (CH3 )3 C < (CH3 )2 C H
· · · ·
(3) (CH3 )2 C H < (CH3 )3 C < (C6 H5 )3 C < (C6 H5 )2 C H
· · · ·
(4) (CH3 )2 C H < (CH3 )3 C < (C6 H5 )2 C H < (C6 H5 )3 C

GC0160

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6. Arrange the carbanions, (CH3)3 C , CCl3 , (CH3)2 CH , C6H5 CH2 , in order of their decreasing stability

[AIEEE-2009]
(1) CCl3 > C6H5 CH2 > (CH3 )2 CH > (CH3 )3 C

(2) (CH3 )3 C > (CH3 )2 CH > C6H5 CH2 > CCl3

(3) C6 H5 CH2 > CCl 3 > ( CH3 )3 C > (CH3 )2 CH

(4) ( CH3 )2 CH > CCl 3 > C6H5 CH2 > ( CH3 )3 C

GC0161
7. The non aromatic compound among the following is :- [AIEEE-2011]

®
(1) (2) (3) (4)
S

GC0162

8. ortho-Nitrophenol is less soluble in water than p– and m– Nitrophenols because :-

(1) Melting point of o–Nitrophenol is lower than those of m– and p– isomers [AIEEE-2012]

(2) o–Nitrophenol is more volatile in steam than those of m– and p– isomers

(3) o–Nitrophenol shows Intramolecular H–bonding

(4) o–Nitrophenol shows Intermolecular H–bonding

GC0163

9. Which of the following compounds are antiaromatic :- [AIEEE-2012(Online)]

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

..
node06\B0BC-BD\Kota\JEE(Advanced)\Leader\Chem\Module\3-EDE-Acidic & Basic-Isomerism\Eng\1_EDE\02. Ex.p65

..
O –

(V) (VI)
+

(1) (III) and (VI) (2) (II) and (V) (3) (I) and (V) (4) (V) and (VI)

GC0164

10. Among the following the molecule with the lowest dipole moment is :- [AIEEE-2012(Online)]

(1) CHCl3 (2) CH2Cl2 (3) CCl4 (4) CH3Cl

GC0165
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11. The order of stability of the following carbocations [JEE-MAIN-2013]

+
CH2
+ +
CH2=CH–CH2 ; CH3–CH 2–CH 2 ; is :-
I II
III

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

GC0166

12. For which of the following molecule significant µ ¹ 0 [JEE-MAIN-2014]

Cl CN OH SH

®
(1) (2) (3) (4)

Cl CN OH SH

(1) Only (3) (2) (3) and (4) (3) Only (1) (4) (1) and (2)

GC0167

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

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

O N O
GC0168

14. The correct order of stability for the following alkoxides is : [JEE-MAIN-2020]

O– O– O–
O2N
NO2 NO2
(A) (B) (C)
node06\B0BC-BD\Kota\JEE(Advanced)\Leader\Chem\Module\3-EDE-Acidic & Basic-Isomerism\Eng\1_EDE\02. Ex.p65

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

GC0194

15. The correct order of heat of combustion for following alkadienes is : [JEE-MAIN-2020]

(a) (b) (c)

(1) (a) < (b) < (c) (2) (b) < (c) < (a) (3) (c) < (b) < (a) (4) (a) < (c) < (b)
GC0195

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16. Among the following compounds, which one has the shortest C—Cl bond ? [JEE-MAIN-2020]
H3C Cl
Cl CH HC Cl
(1) H3C–Cl (2) H3C (3) (4)
CH3 CH 2 CH 2

GC0196

17. Among the following, the aromatic compounds are : [JEE-MAIN-2021]

(A) CH 2 (B) (C) (D)

! Å

Choose the correct answer from the following options :

(1) (A) and (B) only (2) (B) and (C) only

®
(3) (B), (C) and (D) only (4) (A), (B) and (C) only
GC0197

Å Å
CH2 CH2 Å Å
CH2 CH2
H
18. O [JEE-MAIN-2021]
H
(A) (B) (C) (D)
Among the given species the Resonance stabilised carbocations are:
(1) (C) and (D) only (2) (A), (B) and (D) only
(3) (A) and (B) only (4) (A), (B) and (C) only
GC0198

19. Which of the following compounds does not exhibit resonance? [JEE-MAIN-2021]
CH2OH
(1) CH3CH2OCH=CH2 (2)
node06\B0BC-BD\Kota\JEE(Advanced)\Leader\Chem\Module\3-EDE-Acidic & Basic-Isomerism\Eng\1_EDE\02. Ex.p65

(3) CH3CH2CH2CONH2 (4) CH3CH2CH=CHCH2NH2

GC0199

20. The correct decreasing order of densities of the following compounds is : [JEE-MAIN-2021]
Cl Br
Cl

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

(1) (D) > (C) > (B) > (A) (2) (C) > (D) > (A) > (B)
(3) (C) > (B) > (A) > (D) (4) (A) > (B) > (C) > (D)
GC0200
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®

21. Given below are two statements : [JEE-MAIN-2021]

Statement I : Hyperconjugation is a permanent effect.

æ ö+
Statement II : Hyperconjugation in ethyl cation ç CH3 - CH2 ÷ involves the overlapping of Csp - H1s bond
2

è ø
with empty 2p orbital of other carbon.
Choose the correct option :
(1) Both statement I and statement II are false
(2) Statement I is incorrect but statement II is true
(3) Statement I is correct but statement II is false
(4) Both Statement I and statement II are true.

®
GC0201
22. Which of the following is an example of conjugated diketone? [JEE-MAIN-2022]

(1) (2)

(3) (4)

GC0202
23. Which of the following carbocations is most stable : [JEE-MAIN-2022]

OCH3 OCH3
H 3CO
(1) (2) (3) (4) H CO
3

GC0203
node06\B0BC-BD\Kota\JEE(Advanced)\Leader\Chem\Module\3-EDE-Acidic & Basic-Isomerism\Eng\1_EDE\02. Ex.p65

24. Which of the following is not an example of benzenoid compound ? [JEE-MAIN-2022]

NH2
(1) (2) (3) (4)

GC0204

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25. Given below are two statements. One is labelled as Assertion A and the other is labelled as Reason R.
Assertion A : [6] Annulene. [8] Annulene and cis -[10] Annulene, are respectively aromatic, not-aromatic
and aromatic. [JEE-MAIN-2022]

[6] Annulene

[8] Annulene

H H
Cis-[10] Annulene

®
Reason R : Planarity is one of the requirements of aromatic systems.
In the light of the above statements, choose the most appropriate answer from the options given below.
(1) Both A and R are correct and R is the correct explanation of A.
(2) Both A and R are correct but R is NOT the correct explanation of A.
(3) A is correct but R is not correct.
(4) A is not correct but R is correct.
GC0205
26. Increasing order of stability of the resonance structure is : [JEE-MAIN-2023]

A. B.

C. D.

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

GC0206
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27. Given below are two statements, one is labelled as Assertion A and the other is labelled as Reason R.
Assertion A : Benzene is more stable than hypothetical cyclohexatriene. [JEE-MAIN-2023]
Reason R : The delocalized electron cloud is attracted more strongly by nuclei of carbon atoms.
In the light of the above statements, choose the correct answer from the options given below:
(1) A is true but R is false.
(2) A is false but R is true.
(3) Both A and R are correct and R is the correct explanation of A.
(4) Both A and R are correct but R is NOT the correct explanation of A.
GC0207

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EXERCISE # J-ADVANCED
1. Which one of the following has the smallest heat of hydrogenation per mole of H2 ? [IIT-93]
(A) 1–Butene (B) trans–2–Butene (C) cis–2–Butene (D) 1, 3–Butadiene
GC0176
2. Most stable carbonium ion is [IIT-95]
Å Å
(A) p-NO2—C6H4— C H 2 (B) C 6 H 5 C H 2
Å Å
(C) p-Cl—C6H4— C H 2 (D) p-CH3O—C6H4— C H 2
GC0177
3. Arrange the following compounds in order of increasing dipole moment : [IIT-96]
toluene (I) m-dichloroobenzene (II)
o-dichlorobenzene (III) p-dichlorobenzene (IV)

®
(A) I < IV < II < III (B) IV < I < II < III (C) IV < I < III < II (D) IV < II < I < III
GC0178
4. The most unlikely representation of resonance structure of p-nitrophenoxide ion is - [IIT-99]
Å Å Å Å
O–N=O O–N–O O=N=O O–N=O

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

O O O O
GC0179
5. An aromatic molecule will not [IIT-99]
(A) have 4n p electrons (B) have (4n + 2)p electrons
(C) be planar (D) be cyclic
GC0180
6. Statement-I : p-Hydroxybenzoic acid has a lower boiling point that o-hydroxybenzoic acid.
Because
Statement-II : o-Hydroxybenzoic acid has intramolecular hydrogen bonding. [IIT 2003]
(A) Statement-I is True, Statement-II is True ; Statement-II is a correct explanation for Statement-I
node06\B0BC-BD\Kota\JEE(Advanced)\Leader\Chem\Module\3-EDE-Acidic & Basic-Isomerism\Eng\1_EDE\02. Ex.p65

(B) Statement-I is True, Statement-II is True ; Statement-II is NOT a correct explanation for Statement-I
(C) Statement-I is True, Statement-II is False.
(D) Statement-I is False, Statement-II is True.
GC0181
7. Among the following, the molecule with the highest dipole moment is [IIT-2003]
(A) CH3Cl (B) CH2Cl2 (C) CHCl3 (D) CCl4
GC0182
8. Give resonating structures of following compound. [IIT 2003]

OH
GC0183
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9. Which of the following is least stable : [IIT-2005]
Å Å
(A) CH3–O=CH–CH–HC=CH2 (B) CH3–O=CH–CH=HC–CH2
Å 1 Å
(C) CH3–O–CH–CH–HC=CH2 (D) CH3–O–CH–CH–CH=CH2
GC0184
10. Among the following, the least stable resonance structure is - [IIT-2007]
Å O
Å O Å O Å O Å
(A) N (B) Å N (C) Å N (D) Å N

O O O O

GC0185
11. The correct stability order for the following species is : [IIT-2008]
Å Å Å

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O O Å

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

(A) II > IV > I > III (B) I > II > III > IV (C) II > I > IV > III (D) I > III > II > IV
GC0186
12. The correct stability order of the following resonance structures is [IIT-2009]
+ + + +
(I) H 2 C = N = N (II) H 2 C - N = N (III) H 2 C - N º N (IV) H 2 C - N = N
(A) (I) > (II) > (IV) > (III) (B) (I) > (III) > (II) > (IV)
(C) (II) > (I) > (III) > (IV) (D) (III) > (I) > (IV) > (II)
GC0187
13. The total number of contributing structures showing hyperconjugation (involving C–H bonds) for
the following carbocation is. [IIT-2011]
H3C Å CH2CH3

GC0188
14. Which of the following molecules, in pure from , is (are) unstable at room temperature ?
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[IIT-2012]
O O

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

GC0189
15. The hyperconjugative stbilities of tert-butyl cation and 2-butene, respectively, are due to
(A) s®p (empty) and s®p electron delocalisations [IIT-2013]
(B) s®s and s®p electron delocalisations
(C) s®p (filled) and s®p electron delocalisations
(D) p (filled)®s and s®p electron delocalisations
GC0190
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16. The total number of lone-pairs of electrons in melamine is [IIT-2013]

GC0191
17. The number of resonance structures for N is : [IIT-2015]
OH
NaOH
N

GC0192
18. Among the following, the number of aromatic compound (s) is- [JEE - Adv. 2017]

– Å Å

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Å –

GC0193

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ANSWER-KEY
EXERCISE # O-I
1. (D) 2. (C) 3. (B) 4. (A,B,D) 5. 4(b, d, f, g)
6. (a), (c), (d), (g), (j), (l), (m) 7. (A) 8. (A) 9. (A)
10. A,D 11. (D) 12. b, d, e 13. b d e 14. (d) 15. c,f
16. a, b, c, d, f 17. b, c, f 18. 19. a-I , b-II , c-II , d-II , e-I
20. a-I ,b-I, c-I, d-I, e-II, f-II 21. a, e, f, g
22. (a) Resonance forms, (b) A , (c) C , (d) A & B, (e) B & C , (f) 0 , (g) B , (h) B
23. (a) II ; (b) II ; (c) II 24. (A) 25. a-II , b-II , c-II , d-II 26. a&b
27. (i)-I , (ii)-II, (iii)-II, (iv)-I, (v)-I, (vi)-II , (vii)-I, (viii)-II, (ix)-II, (x)-II, (xi)-II ,(xii)-I, (xiii) -I ,
(xiv)-I, (xv)-I

®
28. a-II ,b-I, c-I, d-II, e-I 29. (B) 30. (D) 31. (B) 32. (C)
33. (C) 34. (C) 35. (D) 36. (A,B,C) 37. (B) 38. (B)
39. (C) 40. (D) 41. (D) 42. (A) 43. (B,C,D) 44. (B)
45. (A) 46. (A,C,D) 47. a-I ,b-I, c-II, d-I, e-I, f-I
48. a-II ,b-I, c-I, d-I, e-II, f-II 49. (D) 50. C>B>A 51. (A)
EXERCISE # O-II
1. (i) a, b ; (ii) a ,c ; (iii) b, c, d ; (iv) a, b, c, d, e, f
2. Aromatic®a, b, d, e, g ; Non-aromatic®c, f 3. (C) 4. (C) 5. (B)
H NH2 OH
B C C
O O N N N N
6. (A) 7. (a) (b) (c)
H–B B–H NH2–C C–NH2 HO–C C–OH
O N N

8. (D)
9. (i) c > b > a (ii) c > b > a (iii) b > c > a (iv) d > c > b > a (v) c > b > a
(vi) b > c > a (vii) c > b > a (viii) c>a>d>b (ix) b > c > a (x) c > a > b
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(xi) c > a > b (xii) a > b > c > d (xiii) b>a>c>d (xiv) d > e > b > a > c
(xv) a > c > b (xvi) b > c > a
10. (C) 11. (a) I ; (b) I ; (c) II ; (d) II ; 12. (C) 13. (A) 14. (A)
15. (D) 16. (B)
17. (i) a < b (ii) d < a < c < b (iii) b < a (iv) c < b < a (v) c < a < b (vi) a<c< b
(vii) c < b < a (viii) c < b < a (ix) b < a (x) a < c < b < d
18. (A) 19. (D) 20. (B) 21. (D)
22. (a) IV<I<II < III < V (b) III < IV < I < II 23. (B) 24. (A)
25. (a) -I ; (b) - I ; (c) - II 26. (a) 4658 ; (b) 4638 (c) 4632 ; (d) 4650 ; (e) 5293
27. (A) 28. (B) 29. (D)

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