E

JE
T
II
-F

CONCEPTUAL
B

IMPROVEMENT OF G.O.C.
N
C

1
 ORGANIC chemistry
Time: 15 minutes
1. Draw Resonance hybrid of the following compounds:-

(1) OH (2)
O

(3) (4)
O

E
–
O

JE
O
(5) (6)

O
O

(7) H2C = C – NH – CH3

T (8)
II
–
CH=CH—NH2
-F
:

(9) (10) H2N O

O H
–O O
B

O
(11) (12) H—C
–
O
–
N

O O
+
CH2
(13) (14)
C

 O
(15) Me — S — CH2 (16) CH3 — N
O
O

..
(17) (18) H2N — C  N :

2
 
(19) NO3 (20) O=C=O
Me
(21) O N (22) H2N — C — NH 2

NH

:
O
(23) (24)
+ OH
O O +

E
(25) (26)
–

JE
O
–

(27) (28)
–
:O:

T
II
(29) (30) –
O—C=O
–
O
-F

–
O
–
CH2 NH2
B

(31) (32)

NO2
N
C

3
----------------------------------------------------------------------------------------------------
 ORGANIC chemistry
Time: 15 minutes
1. Compare relative stability of following resonating strutures
S.No. Resonanting structures Order of stability Reason
 
(1) H2C = CH — Cl H2C — CH = Cl
(a) (b)
O O–

E
(2)

(a) (b)

JE
 
(3) CH2 — CH = NH H2C = CH — NH
(a) (b)
 
(4) CH3 — O — CH2 CH3 — O = CH2
(a)
 
(b)

T  
II
(5) H—N=C=O H— N C— O H — N— C  O
(a) (b) (c)
:

Me N Me + N –
-F

(6)
: :

O O O O
:

(a) (b)
H
O+ OH
(7)
+
B

(a) (b)
+
N

(8)
+ +
(a) (b) (c)
C

O O–

(9) –
O O
(a) (b)
S S–
(10)
– H H
(a) (b)

4
----------------------------------------------------------------------------------------------------
S.No. Resonanting structures Order of stability Reason
+ – ..
(11) H — O = C = N: H — .O. — C  N:

:
(a) (b)
O– O O
–
(12) C
N N N–
(a) (b) (c)

E
O O– O
+ +

JE
(13) C C C
N N N–
(a) (b) (c)
O O– O–
(14) – – C

T
+
H CH2 H CH2 H CH2
(a) (b) (c)
II
+
:
: :

O O
+
(15)
-F

(a) (b)
–
N N

(16) –
B

(a) (b)
O O O– O
N

–
(17)
C

(a) (b)
N:
(18) +
+ N
:

(a) (b)
O O– O

(19)
– –
(a) (b) (c)

5
----------------------------------------------------------------------------------------------------
 ORGANIC chemistry
Time: 15 minutes
1. Compare relative stability of following resonating strutures
S.No. Resonanting structures Order of Reason
stability
+
– + –
(1) O CH2 O CH2 O CH2

E
(a) (b) (c)
+  ..
:

(2) H2N — CH = NH 2 H2N  CH — NH2

JE
(a) (b)
O O +O O
+
(3)

(a)
O– T
(b)
II
O
(4) Me — N + Me — N +
–
O O
-F

(a) (b)
– + +
:

(5) H—C = N = N—H H—C—N—N—H

–
(a) (b)
 
(6) H3C — HC = C = O Me — CH — C  O
B

(a) (b)
O O–
–
N

(7)
:

H—C—N—H H—C = N—H

:

(a) (b)
O O–
C

–
(8) CH3—C—CH2 CH3—C = CH2
(a) (b)
+ +
(9) CH2 — C = C — CH3 CH2 = C — C —CH3
H H H H
(a) (b)
O O–
(10) C C –
– –
O O O O
(a) (b)

6
----------------------------------------------------------------------------------------------------
S.No. Resonanting structures Order of Reason
stability

(11) H H
(a) (b)
– – –
– O O O
N N N
(12)
(a) (b) (c)
O O–

E
(13)
–

JE
(a) (b)
O– O

(14)

Cl Cl –
T
II
(a) (b)
 
(15) Me — CH = C = CH Me — CH — C  CH
-F

(a) (b)

..  
(16) Me — .O. — CH = CH — CH2 Me — O
. . = CH — CH = CH2
(a) (b)
B

(17)
–
: :

S S
–
N

(a) (b)
  + –
(18) O=C=O O—CO O=C—O
(a) (b) (c)
C

+ –
:

(19) H2N — C = N: H2N = C = N:

(a) (b)
O O–
(20)
+
: :

Me OH Me O–H
(a) (b)

7
----------------------------------------------------------------------------------------------------
 ORGANIC chemistry
Time: 15 minutes
1. Identify no. of -hydrogen in the following compounds

No of -hydrogen No. of -hydrogen

CH3
(1) (2)

E
JE
(3) (4)

T CH3
II
(5) (6)
CH3
-F

H 3C

CH3
(7) (8)
B

CH3

CH3
N

CH3

CH3
C

(9) (10)
CH3 CH3
CH3

(11) (12)

CH3

8
----------------------------------------------------------------------------------------------------
 No of -hydrogen No. of -hydrogen

CH3 CH3
(13) (14) H2C
CH3

CH3 H 3C
(15) H3C (16) CH3

E
H 3C

(17) H3C (18) H 3C

JE
CH3 CH3

CH3

CH3
H3C CH3
(19) H3C CH3

T (20)
H 3C
H 3C
II
-F
B
N
C

9
----------------------------------------------------------------------------------------------------
 ORGANIC chemistry
5 Time: 15 minutes
1. Identify no. of -hydrogen in the following compounds

No of -hydrogen No. of -hydrogen

H2C CH3
(1) (2)
CH3
CH3

E
(3) (4)

JE
H3C H3C CH3

(5)

CH3
T (6)
II
H 3C CH3
-F

(7) (8)

H 3C
CH3
B

(9) (10)

H3 C
N

H2C H 3C
C

(11) (12)

CH3

(13) (14)

10
----------------------------------------------------------------------------------------------------
 No of -hydrogen No. of -hydrogen
H2C H 3C

(15) (16)

CH3 CH3
(17) (18)
CH3 CH3
CH3 CH3

E
(19) (20) CH3

JE
H3C
H 3C CH3
H3C
CH3
CH3

T
(20) H 3C
H 3C
H3C
CH3
II
-F
B
N
C

11
----------------------------------------------------------------------------------------------------
 ORGANIC chemistry
6 Time: 15 minutes
Q.1 Given the relative Stability of the following compound

1.
H
(i) ii) (iii) (iv) (v)

Me Me Me

E
2. Ph — CH2 — CH = CH — C — Me Me — CH — CH = CH — C — Me
Me Me

JE
(i) (ii)
Me Me Me
PH — CH = CH — C — Me Me — C — HC = CH — C — Me
Me Me Me
(iii) (iv)

3.
+
Me — CH — CH — CH3 Me — CH2
+
T +
CH3
Me
Me — C — CH2 +
II
Me Me
(i) (ii) (iii) (iv)
-F

+
+ + +
4.

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

B

+ +
5. +
+
N

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

C

6.

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

7. H2C = C = CH2 Me — CH = CH2

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

12
----------------------------------------------------------------------------------------------------
 ORGANIC chemistry
Time: 15 minutes
Q.1 Given the relative Stability of the following compound

1.

(i) (ii) (iii) (iv) (v) (vi) (vii)

E
2.

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

JE
+ + + +
CH2 CH2 CH2 CH2

3.

CH3 CD3 CT3

T
II
(i) (ii) (iii) (iv)

+ Me + + +
CH2 CH2
-F

CH CH2

4.

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

B

+ + + +
CH2 CH2 CH2 CH2
N

5.
C

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

– – – –
CH2 CH2 CH2 CH2

6.

CF3 CCl3 Me
(i) (ii) (iii) (iv)

13
----------------------------------------------------------------------------------------------------
 ORGANIC chemistry
Time: 15 minutes
Q.1 Given the relative Stability of the following compound

1.

(i) (ii) (iii)

+ +

E
2.
+
+

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

+   +
3. CH2 (Et)2 CH (Et)3 C CH2—CH2

(i) (ii)

T (iii) (iv)
II
+
4. +
CH + 
-F

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

5.
B

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

N

6.

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

C

7.

(i) (ii) (iii)

14
----------------------------------------------------------------------------------------------------
 ORGANIC chemistry
9 Time: 15 minutes
Q.1 Given the relative Stability of the following compound

1.

(i) (ii) (iii)

E
2.

(i) (ii) (iii)

JE
3.

(i) (ii)

(iii)
T
II
4.
-F

(i) (ii) (iii)

5.
B
N

(i) (ii) (iii)

6. CH3 — C  C — CH3 H3C — CH2 — C  CH

(i) (ii)
C

C C C C C C
7. H3C — C  C — CH3

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

CH3 H 3C

8.

(i) (ii)
15
----------------------------------------------------------------------------------------------------
 ORGANIC chemistry
10 Time: 15 minutes
Q.1 Given the relative Stability of the following compound
H 2C

1. 2.

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

E
JE
CH3 CH3
3. 4.

CH3

T
CH3
(i) (ii) (i) (ii) (iii)
II
CH2 CH3
-F

CH3 CH3
5. 6.

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

B
N

7. 8.
C

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

H3O H3O
O O

CH2 CH3
9. 10.

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

Q.2 Hyperconjugation involves

(A) Delocalization of s-electrons into an adjacent p-bond.
(B) Delocalization of n-electrons into an adjacent double bond.
(C) Delocalization of -electrons into an adjacent double bond.
(D) All are true
 16
----------------------------------------------------------------------------------------------------
 ORGANIC chemistry
11 Time: 15 minutes
Q.1 Hyperconjugation is possible in
(A) alkenes (B) alkynes (C) carbocations (D) all of these

Q.2 Hyperconjugation is possible in

(A) Free radicals (B) Carbanions (C) Alcohols (D) Amines

Q.3 Hyperconjugation occurs in

(A) CH3 — CH = CH2 (B) CH3 — CH2 — CH = CH2
CH3

E
(C) CH = CH2 (D) all ot these
CH3

JE
Q.4 Hyperconjugation occurs in
CH 3
(A) CH3 — C — CH = CH2 (B) CH3 — CH = CH — CH3
CH3


T
(C) Ph — CH = CH2 (D) CH3

Q.5 Hyperconjugation occurs in

II
CH3 CH3 CH3 CH3
C CH3
CH3
(A) (B) (C) (D)
-F

Br
CH3 CH3

Q.6 Hyperconjugation occurs in

+ +
CH2
B

(A) (B)

+
CH
N

(C) (D) all of these

C

Q.7 Hyperconjugation occurs in

CH3
 
(A) CH3 (B) CH3  CH2 (C) CH3 (D) both (B) and (C)
CH3

CH3
Q.8
CH3
How many hyperconjugable H-atoms does this cation has?
(A) 10 (B) 6 (C) 12 (D) 15

17
----------------------------------------------------------------------------------------------------
 CH3
Q.9 CH3
CH3 CH3
How many hyperconjugable H-atoms does this cation has?
(A) 5 (B) 6 (C) 12 (D) 8

HB
Q.10 HA — C — CH = CH 2
HC
Canonical structures due to hyperconjugation in this molecules can be written as
HB HA – HA
– –

E
(A) C = CH — CH2 C = CH — CH2 C = CH — CH2
HC HA+ HC HB+ HB HC+

JE
HB HA HA
+ + +
(B) C = CH — CH2 C = CH — CH2 C = CH — CH2
HC HA– HC H–B HB HC–

(C) both (A) and (B)

(D) none of these

CH3 CH3

T CH3
II
Q.11
-F
CH3 CH3 CH3
I II III
Among these compounds, which of the following orders is correct for their nobond-resonance
energy?
(A) III > II > I (B) I > II > III (C) I > III > II (D) II > III > I

Q.12 Compound Homolytic bond

B

dissociation energy
 
CH4  CH3  H 104 Kcal/mol
CH3 CH3

N

CH3 — CH CH 3 — C H 92 Kcal/mol
CH3 CH3
Notice the hemolytic bond-dissociation energy of the alkanes. Now, ignoring the contribution of
C

inductive effect, no-bond-resonance energy of tert-butyl radical can be calculated to be

(A) 6 Kcal/mol (B) 10 Kcal/mol (C) 12 Kcal/mol (D) 14 Kcal/mol

Q.13

I II III
Among these cycloalkenes, which of the following orders of stability is correct?
(A) I > II > III (B) III > II > I (C) II > I > III (D) II > III > I

18
----------------------------------------------------------------------------------------------------
Q.14

I II III
Among these dienes, which of the following orders of stability is correct?
(A) I > II > III (B) III > II > I (C) II > III > I (D) II > I > III

CH3
Q.15 CH3

I II III IV
Which of the following statements is correct, about these cycloalkenes?

E
(A) Stability difference between I and II is more than that between III and IV
(B) Stability difference between I and II is less than that between III and IV
(C) Overall, stability order is I > II > III > IV

JE
(D) None of these

CH3
Q.16 I C = CH2
CH3

CH3 CH3
II
H
C=C
H

T
II
CH3 H
III C=C
H CH3
Which of the following orders is correct for heat of combustion of these isomeric alkenes?
-F

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

Q.17 CH2 = CH — C  C — CH = CH2

I II
B

Which of the following orders is correct for heat of combustion of these isomers?
(A) I > II (B) II > I (C) I = II (D) Not predictable
N

Q.18
C

I II III
Which of the following order is correct for heat of combustion of these isomers?
(A) I > II > III (B) III > II > I (C) II > III > I (D) I > III > II

CH2 — CH2 — CH3 CH3 CH3

Q.19
CH2CH3 CH3 CH3
I II III
Which of the following orders is correct for heat of hydrogenation of these compounds?
(A) I > II > III (B) III > II > I (C) II > I > III (D) I > III > II

19
----------------------------------------------------------------------------------------------------
Q.20

I II III
Which of the following orders is correct for heat of hydrogenation of these compounds?
(A) I > II > III (B) III > II > I (C) III > I > II (D) II > III > I

Q.21
I II III

E
Which of the following orders is correct for heat of hydrogenation of these compounds?
(A) I > II > III (B) III > II > I (C) II > I > III (D) I > III > II

JE
Q.22

I II III
Which of the following orders is correct for heat of hydrogenation of these compounds?

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

CH3
II
Q.23 CH3 CH2

I II III
-F

Which of the following orders is correct for heat of hydrogenation of these compounds?
(A) I > II > III (B) III > II > I (C) III > I > II (D) II > I > III

CH3 CH2 CH3

Q.24
CH3 CH3 CH3
B

I II III
Which of the following order is correct for heat of hydrogenation of these compounds?
(A) I > II > III (B) III > II > I (C) II > III > I (D) III > I > II
N

CH3

Q.25 a b
C

CH3
a and b are the length of these two C = C bonds. Now, which of the following orders is correct?
(A) a = b (B) a < b (C) b > a (D) Not predictable

CH3

Q.26 a b c
CH3
a, b and c are the length of these C = C bonds. Now, which of the following orders is correct?
(A) a = b = c (B) a > b > c (C) c > b > a (D) b > c > a

20
----------------------------------------------------------------------------------------------------
Q.27 Inductive effect of – NO2 group operates in
NO2 NO2 NO2
(A) (B) (C) (D) all of these

Q.28 Inductive effect of – CH3 group operates in

CH3 CH3 CH3
(A) (B) (C) (D) both (B) and (C)

E
– 
Q.29 — CH3 —C—O —O
I II III

JE
Which of these groups has + I effect?
(A) I (B) II (C) III (D) all of these

–
Q.30

(B) sp2
T
Hybridization of the negatively charged C-atom of this anion is
(A) sp3 (C) sp (D) unhybridized
II
-F


B
N
C

21
----------------------------------------------------------------------------------------------------
 ORGANIC chemistry
12 Time: 15 minutes

+
Q.1

Empty orbital of this carbocation is

(A) 2p (B) sp3 (C) sp2 (D) sp

Q.2 Negative charge of which the following carbanions is not resonance – stabilized?
– –

E
(A) (B) (C) (D)
– –

JE
OCH3 OCH3
OCH3

+
Q.3
+ OCH3
OCH3

T
+
OCH3
I II III
II
Which of the following orders is correct for the stability of these carbocations?
(A) I > II > III (B) III > II > I (C) I > III > II (D) II > III > I

+
-F

Q.4 I
O

+
II N
CH3
B

+
II O
Which of the following orders is correct for the stability of these carbocations?
N

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

+
+ +
C

Q.5

I II III
Which of the following orders is correct for the stability of these carbocations?
(A) I > II > III (B) III > II > I (C) II > I > III (D) II > III > I

+
Q.6 + +

I II III
Which of the following orders is correct for the stability of these carbocations?
(A) I > II > III (B) III > II > I (C) I > III > II (D) II > I > III

22
----------------------------------------------------------------------------------------------------
 +
Q.7 I C

+
II CH2

+
CH2

E
III

JE
Which of the following orders is correct for the stability of these carbocations?
(A) I > II > III (B) III > II > I (C) II > I > III (D) III > I > II

+
+ +
Q.8

I II

T III
Which of the following orders is correct for the stability of these carbocations?
II
(A) I > II > III (B) III > II > I (C) II > I > III (D) II > III > I

Q.9 Which of the following reactions is not possible?

+ –
-F

ClO4
HClO4
(A) OH  + H2O

+ –
ClO4
HClO4
(B) OH  + H2O
B

(C) both (A) and (B)

(D) none of these
N

Q.10 Which of the following reactions is not possible?

AgClO4
(A) Cl   OH
C

HO 2

AgClO4
(B) Cl   OH
H2O

(C) both (A) and (B)

(D) none of these

23
----------------------------------------------------------------------------------------------------
 – – –
Q.11 CH3 — CH2 CH3 — CH — CH 3 CH3 — C — CH 3

CH3
I II III
Which of the following orders is correct for the stability of these carbanions?
(A) I > II > III (B) III > II > I (C) II > I > III (D) I > II > III

–
CH2
– –
Q.12 CH3 — CH2 CH2 = CH — CH 2

E
I II III
Which of the following orders is correct for the stability of these carbanions?
(A) I > II > III (B) III > II > I (C) II > III > I (D) II > I > III

JE
– – –
Q.13
CH3 Cl
I II III

(B) III > II > I

T
Which of the following orders is correct for the stability of these carbanions?
(A) I > II > III (C) III > I > II (D) II > III > II
II
– –
Cl –
-F

Q.14

Cl
Cl
I II III
Which of the following orders is correct for the stability of these carbanions?
(A) I > II > III (B) III > II > I (C) II > I > III (D) II > I > III
B

– –
–
NO2
N

Q.15
NO2
NO2
C

I II III
Which of the following orders is correct for the stability of these carbanions?
(A) I > II > III (B) III > II > I (C) II > I > III (D) II > III > I


Q.16 – CH2 = CH — CH2
–
I II III
Which of the following orders is correct for the stability of these carbanions?
(A) I > II > III (B) III > II > I (C) I > III > II (D) II > III > I

24
----------------------------------------------------------------------------------------------------
 
Q.17 I CH2 — CH = CH2

II CH2 — CH = O

III CH2 — CH2 — CH3
Which of the following orders is correct for the stability of these carbanions?
(A) I > II > III (B) III > II > I (C) II > I > III (D) II > III > I

Q.18 – O – O

E
O O O
I II III
Which of the following orders is correct for the stability of these carbanions?

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

– –
O O O O
Q.19
O O
I
–
II
Which of these carbanions is sp3 hybridized?
T III
II
(A) I (B) II (C) III (D) nonw of these

CH3
 
-F
Q.20 CH2 = CH — CH2 CH3 — CH2 CH3 — C
CH3
I II III
Which of the following orders is correct for the stability of these radicals?
(A) I > II > III (B) III > II > I (C) I > III > II (D) III > I > II

CH2 CH2 CH2

B

Q.21
N

CH3 CH3
CH3
I II III
C

Which of the following orders is correct for the stability of these radicals?
(A) I > II > III (B) III > II > I (C) II > I > III (D) II > III > I

CH3
Q.22 CH3 — H CH3CH 2 — H CH3 — H
H
I II III
Which of the following orders is correct for the energy required for homolytic cleavage of indicated
C – H bonds?
(A) I > II > III (B) III > II > I (C) III > I > II (D) II > III > I

25
----------------------------------------------------------------------------------------------------
Q.23 I II III
CH2 — H CH2 — H
CH2 — H

Which of the following orders is correct for energy required for homolytic cleavage of indicated C –
H bonds?
(A) I > II > III (B) III > II > I (C) II > I > III (D) III > I > II

Q.24 I Cl — CH2 — COOH

E
II Br — CH2 — COOH

III I — CH2 — COOH

JE
Which of the following order is correct for the acidic strength of these carboxylic acids?
(A) I > II > III (B) III > II > I (C) II > I > III (D) II > III > I

Q.25 I Cl — CH2 — COOH

T
II O2N — CH2 — COOH

III CH3 — COOH

II
Which of the following order is correct for the acidic strength of these carboxylic acids?
(A) I > II > III (B) III > II > I (C) II > I > III (D) II > III > I
-F

COOH
COOH
Q.26 H2C HCOOH
COOH COOH
I II III
Which of the following order is correct for the acidic strength of these carboxylic acids?
(A) I > II > III (B) III > II > I (C) II > I > III (D) II > III > I
B

CH3
N

Q.27 CH3 — Si —— CH2 — COOH

CH3
In this molecule, the effect of trimethylsilyl group (encircled) on the acidity of – COOH group is of
C

(A) strong electron donating nature (B) strong electron withdrawing nature
(C) weak electron withdrawing nature (D) both (A) and (C)

OH OH OH

Q.28
O O
O O
O
I II III
Which of the following order is correct for the acidic strength of these compounds?
(A) I > II > III (B) III > II > I (C) II > I > III (D) III > I > II

26
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 1 2
OH OH

OH 3
Q.29 O O

4 OH
Which of these – OH groups is most acidic?
(A) 1 (B) 2 (C) 3 (D) 4

H 3

E
H 2

JE
Q.30
O O
H1
Which of the following orders is correct for the acidity of these indicated H-atoms?
(A) 1 > 2 > 3 (B) 3 > 2 > 1 (C) 2 > 1 > 3 (D) 1 > 3 > 2

T
II

-F
B
N
C

27
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 ORGANIC chemistry
13 Time: 15 minutes
1. Identify the Nature of compound
S.No. Compound Aromatic Anti-aromatic Non-aromatic

(1)

–
(2)

E
+
(3)

JE
+
(4)
+
–

T
(5)
–
(6)
II
(7)
-F

(8)

–
B

(9)

+
N

(10)
C

(11)
B
H

(12)
O O
+

(13) O O
B
H

28
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 ORGANIC chemistry
14 Time: 15 minutes

S.No. Compound Aromatic Anti-aromatic Non-aromatic

(1)

(2)
O

E
(3)

JE
S

(4)

N
H

(5)
T
II
O
+
-F

(6)
O

(7)
O
B

(8)
N

O
+
C

(9)

(10)

(11)
O
O

29
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 ORGANIC chemistry
15 Time: 15 minutes

S.No. Compound Aromatic Anti-aromatic Non-aromatic

O

(1)
O

E
(2)

JE
N O
H
O

(3)
N
H
T
II
N
(4)
-F

N
N
(5)
N
B

(6)
N
N

(7)
C

+
N
H

N N—H
(8)

+
M—N N—H
(9)

30
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 ORGANIC chemistry
16 Time: 15 minutes
1. Identify the Nature of compound
S.No. Compound Aromatic Anti-aromatic Non-aromatic

–
(1)

E
(2)

JE
T
(3) II
CH3
B
-F
(4)

(5)
+
N
B

(6)
N

N
H
C

(7) :S:
N

(8)
N
O

N N
(9)
N N
H N

31
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 ORGANIC chemistry
17 Time: 15 minutes

S.No. Compound Aromatic Anti-aromatic Non-aromatic

(1)

E
JE
(2)

(3)
T
II
-F

(4)

(5)
B

+
CH2
N

(6)

–
C

CH2
(7)

(8)
N
O

(9)

32
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 ORGANIC chemistry
- 18 Time: 15 minutes

S.No. Compound Aromatic Anti-aromatic Non-aromatic

O

(1)

E
(2)

JE
O

(3)

N H

(4)
T
II
CH2
-F

(5)

(6) –
B

(7)
N
C

(8)

(9)

33
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 ORGANIC chemistry
19 Time: 15 minutes

S.No. Compound Aromatic Anti-aromatic Non-aromatic

(1)

E
JE
H
B
H—N N—H
(2)
H—B B—H
N

T
H
Borazole
I
II
(3)
-F

(4)

*
(2) (C* = C14) KH 
 (A) + gas (Identify A, B, C, D)
B

+
H

B+C+D
N

(3) Determine the number of  electrons for each compound below, then indicate whether they are
aromatic, antiaromatic, or neither. Assume the molecules are neutral and planar unless otherwise
indicated.
NH2
C

Et
O
N
N
S
B N N
H H
Number of Number of Number of Number of
 electrons:_____  electrons:_____  electrons:_____  electrons:_____
Aromatic, Aromatic, Aromatic, Aromatic,
Antiaromatic, Antiaromatic, Antiaromatic, Antiaromatic,
or or or or
Neither ? Neither ? Neither ? Neither ?

34
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 ORGANIC chemistry
20 Time: 15 minutes
1. Compare Acidic Strength
S.No. Compound Compare Compare
Ka value pKa value
a b a b
COOH COOH
CH3
(1)

E
(a) (b)
COOH COOH

JE
CH3
(2)

(a) (b)

T
II
(3)
-F

(a) (b)

(4) CH CH2
B

(a) (b)
N

O O

(5) O
C

O
(a) (b)

O O O

OMe
(6)
O O
(a) (b)

35
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S.No. Compound Compare Compare
Ka value pKa value
a b a b

:
OH NH2

(7)

(a) (b)

:
:OH NH2

E
(8)

JE
(a) (b)
OH OH

(9) OCH3 CN
T
II
(a) (b)
(10) Cl—CH2—CH2—COOH CH3— CH—COOH
-F
Cl
(a) (b)

(11) OH OH
(a) (b)
(12) HF NH3
B

(a) (b)
..
(13) HC  CH NH3
(a) (b)
N

(14) CH4 NH3

(a) (b)
..
C

(15) HC  N NH3
(a) (b)
OH OH

(16) O O
(a) (b)

36
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 ORGANIC chemistry
-21 Time: 15 minutes
1. Compare Acidic Strength
S.No. Compound Compare Compare
Ka value pKa value
a b a b
O OH
O

(1) Ph — S — OH

E
O
(a) (b)

JE
O
(2) R — OH R — C — OH
(a) (b)
O OH O OH

(3)
Me

T
II
Me
-F
(a) (b)
O OH OH

(4)
B

Me
(a) (b)
OH
N

OH
(5) F
F
(a) (b)
C

+ OH OH
(6) R 3N N C
(a) (b)
(7) CH4 HF
(a) (b)
(8) HF HI
(a) (b)
(9) H2S H2O
(a) (b)

37
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S.No. Compound Compare Compare
Ka value pKa value
a b a b

(10)

(a) (b)

(11) N N O2N N
(a) (b)
O2N
(12)

E
N N N
(a) (b)
O O

JE
OEt H
(13)
OEt H
O O

(14)
(a)
N
(b)

T
F
II
(a) (b)
(15) CCl3OH CF3OH
(a) (b)
-F

(16)

(a) (b)
OH OH
B

(17)
Cl Br
(a) (b)
N

O O
(18)
OH OH
C

(a) (b)
O O
(19) OH OH
(a) (b)
(20) CHCl3 HCF3
(a) (b)

38
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 ORGANIC chemistry
- 22 Time: 15 minutes

Q.1 Rank the following in order of decreasing acidity. +

:
N
+O N
H H HO CH3 H CH3

Q.2 Consider the following compound. Rank the labeled proton in increasing order of acidity
x
O COOH

E
(a) OH
c (b) F F Write the stepwise ionization of acid
HO COOH y
a

SH COOH

JE
b z

Q.3 Write correct order of acidic strength as a to d.

(a) H (b)
O
H N (c)

T
N
H
H
II
H H O
(d)
OH OH
-F

I Me
Q.4 Among & which is more acidic & why? Explain through canonical
I Me
NO2 NO2
forms.
B

Questions No. 5 to 7 (3 questions)

(b)
HOH2C
N

H (c) CH3 O
O OH (a)
H (d) CH3
C

Cortisone

O
H
Q.5 Cortisone contains which functional groups?
(A) Ether, alkene, alcohol (B) Alcohol, ketone, amine
(C) Alcohol, ketone, alkene (D) Ether, amine, ketone

Q.6 Total stereoisomer of the compound Cortisone is

(A) 32 (B) 64 (C) 66 (D) 128

Q.7 Total number of chiral center in Cortisone:

(A) 4 (B) 5 (C) 6 (D) 7
39
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Q.8 Which order of acid strength is wrong
COOH COOH NO2 COOH
CH3
(A) > (B) >

SO3H COOH

COOH COOH Cl COOH

E
(C) > (D) >

JE
OCH3 COOH

Q.9 Which is the order of acidity of the following compounds?

EtCO2H CH3CO2H CH3SO3H CF3SO3H
a b c d
(A) b > a > d > c (B) d > c > a > b (C) d > c > b > a (D) d > a > b > c

Q.10
4
3
2 1
T
Which of the following carbon will be deprotonatated first on treatment with base.
II
5
O
N
-F
(A) 4 (B) 5 (C) 2 (D) 3
B
N
C

40
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 ORGANIC chemistry
-23 Time: 15 minutes
1. Compare which is more basic in nature
S.No. Compounds Compare Compare
Kb value pKb value
a b a b
NH2 NH2
CH3
(1)

E
(a) (b)
NH2 NH2

JE
CH3
(2)

(a) (b)

(3)
T
II
N N
H
(a) (b)
-F

(4)
O N
H
(a) (b)

N—H N:
B

(5)

O
N

(a) (b)

H H
N N
C

(6)
(a) (b)

N
(7)
N N

(a) (b)

41
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 ORGANIC chemistry
24 Time: 15 minutes
1. Compare which is more basic in nature
S.No. Compounds Compare Compare
Kb value pKb value
a b a b

(1) N N
N

(a) (b)

E
H
N

JE
(2)
N
(a) (b)
:

NH2
:

NH2

(3)

T
II
CH3
(a) (b)
NH2
-F

CH3
(4) Ph — NH — Me

(a) (b)
(5) Ph — NH — Me Ph — N — Me
B

Me
(a) (b)
N

NH2
Me
(6)
C

NH2

(a) (b)
(7) H2N — C = NH H2N — C = NH
NH2 CH3
(a) (b)
NH2 NH2
Me Me
(8)

(a) (b)

42
----------------------------------------------------------------------------------------------------
S.No. Compounds Compare Compare
Kb value pKb value
a b a b

N
(9)
N
(a) (b)
O

(10)
N N

E
H
(a) (b)
S

JE
(11)
N N
H H
(a) (b)
– –

(12)

T
II
(a) (b)
– –
O CH2
-F

(13)

(a) (b)

HN NH HN NH2
B

(14)
N

NH2
(a) (b)
C

HN NH2 HN NH2

(15)

NO2 Cl
(a) (b)

43
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 ORGANIC chemistry
25 Time: 15 minutes
Q.1 Which Nitrogen is most basic
a
NH2
b Me
N
(i) (ii)
N N N
a b c
H

E
b
NH2 a
O
a N

JE
(iii) (iv)

: :
H 2N C O N: b

a
N—H

(v) CH3 — C
NH a

T (vi)
c
H—N N—H
b
II
NH2 b

a
NH2
-F

O
(vii) NH2 — C — CH 2 — CH 2 — NH (viii)
a b
N
b
H
B

2. Which is more basic & why?

H O
OMe C
N
C

CH3 NH
C C
H2N NH H2N NH
(i) (ii)

44
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