Aromaticity 1

CSIR NET CHEMICAL SCIENCE

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 Aromaticity 2

1. Among the carbocations given below [NET JUNE 2011]

(a) A is homoaromatic, B is antiaromatic and C is aromatic.

(b) A is aromatic, B is antiaromatic and C is homoaromatic.
(c) A is antiaromatic, B is aromatic and C is harmoaromatic.
(d) A is homoaromatic, B is aromatic and C is antiaromatic.
2. Among A–C, the aromatic compounds are [NET DEC 2011]

(a) A, B and C (b) A and B only (c) B and C only (d) A and C only
3. The correct order of acidity of the compounds A–C is: [NET DEC 2012]

(a) A > B > C (b) B > C > A (c) C > A > B (d) B > A > C
4. Amongst the following, the compound which has the lowest energy barrier for the cis-trans
isomerisation is: [NET DEC 2013]

5. The compound that is antiaromatic is [NET DEC 2014]

(a) I (b) II (c) III (d) IV

6. The compound that gives precipitate on warming with aqueous AgNO 3 is [NET JUNE 2015]
 Aromaticity 3

7. Correct match for the products of the reactions in Column –A with the properties in Column –B is
[NET DEC 2016]
Column-A Column-B
(I) (P) Aromatic

(II) (Q) Antiaromatic

(III) (R) Non-aromatic

(IV) (S) Homoaromatic

(a) (I)-P; (II)-S; (III)-R; (IV)-Q (b) (I)-P; (II)-R; (III)-Q; (IV)-S
(c) (I)-Q; (II)-R; (III)-S; (IV)-P (d) (I)-S; (II)-Q; (III)-R; (IV)-P
8. The correct statement about following species is: [NET JUNE 2018]
O

(A) (B)
(a) Both A and B are aromatic (b) A is aromatic and B is antiaromatic
(c) A is non-aromatic and B is antiaromatic (d) A is aromatic and B is homoaromatic
9. Which of the following species is/are aromatic? [NET SEP 2022]

(a) Only A (b) Only B and C (c) Only A and B (d) Only B

ANSWER KEY
1. A 2. C 3. C 4. C 5. A 6. C 7. A 8. B 9. C

SOLUTION
 Aromaticity 4

1.
Ans. (a)
Sol.

(A) Homoaromatic character

(Aromatised by bypassing the sp3–carbon atom)

2.
Ans. (c)
Sol. Since in case of A the hydrogens present at 1st and 6th position repel each others. Hence planarity of
distorts. While in case of B and C this type of planarity is maintained.

3.
Ans. (c)
Sol.
 Aromaticity 5

Acidity  E.W. tendency.

4.
Ans. (c)
Sol.

Among all options,(c) has gain aromaticity in both the rings. Therefore, the lowest energy barries for
cis-trans isomerisation is option (c)
5.
Ans. (a)
Sol. For antiaromaticity, there are 4ne and there must be delocalization. Since boron is electron deficient, it
has vaccant p-orbital and thus electron can be delocalized.
In the given compound I species has 4ne–.
Thus it is antiaromatic.

6.
Ans. (c)
Sol. Those compound gives precipitate on warming with aqueous AgNO3. Which is more stable
 Aromaticity 6

7.
Ans. (a)
Sol.

8.
Ans. (b)
Sol.

A is completely conjugated planar compound having 6e–s (4n+2)  electron, n = 1)

 Aromaticity 7

Thus, it is aromatic
On the other hand B having 8e– s(4ne– ; n = 2). Thus, it is antiaromatic
9.
Ans. (c)
Sol.

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