DPP- (5) AROMATICITY
1. The given molecules is/are :
2–
–A
S
–B
(a) A– Aromatic (b) A-Aromatic
B – Aromatic B – Aromatic
(C) A– Anti-Aromatic (b) A-Aromatic
B – Non-Aromatic B – Aromatic
2. Which among the following is more acidic ?
(A) (B)
(a) A (b) B
(c) Both are equally Acidic (d) Can’t be predicted.
DPP-(5) / CSIR-NET / AROMATICITY
3. Among the carbocations given below
H
H
(A) (B) (C)
(a) A is homoaromatic, B is antiaromatic and C is aromatic
(b) A is aromatic, B is antinromatic 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
4. Among the following compounds, the one which has highest dipole moment is
(a) (b) (c) (d)
5. The correct order of pKa values for the compounds X, Y and Z is
O CN H H
CN
CN
N H
CN H
O CN
X Y Z
(a) X > Y > Z (b) Y > Z > X (c) Z > X > Y (d) Y > X > Z
6. Correct match the products of the reactions in Column A with the properties in Column B is :
Column A Column B
(a) +2K (i) aromatic
(b) +H2SO4 (ii) antiaromatic
H
Heat
(iii) non-aromatic
(c)
H
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7. The correct statement about aromaticity of given compounds is :
(A) (B)
(a) A is more aromatic than B (b) B is more aromatic than A
(c) Both the structure have equal aromaticity.
(d) Cannot be compared.
+2K (iv) homoaromatic
(d)
(A) (B) (C) (D)
(a) (i) (iv) (iii) (ii)
(b) (i) (iii) (ii) (iv)
(c) (ii) (iii) (iv) (i)
(d) (iv) (ii) (iii) (i)
8. Which of the following structure is not an aromatic ?
O O–
O O
(a) (b) (c) (d)
O O
O +O +
9. Which is the most likely to be protonated in the molecule below ?
H
A B
N N
N N C
D
(a) A (b) B (c) C (d) D
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10. Which of the following structure is anti-aromatic ?
HO O
(a) (b) (c) (d)
HO O
11. Which of the following structure is Anti-aromatic ?
N O
N B H
(a) (b) (c) (d)
N O O
12. The molecule/compound that have the highest dipole moment is :
(a) Nepthaline (b) Phenanthrene (c) Anthracene (d) Azulene
13. If we have to convert 1; 3; 5-Cyclo-hepta triene to an aromatic substance by :
(a) Hydrogen atom abstraction (b) Hydride abstraction
(c) Proton abstraction (d) H2 elimination
14. Which structure shows the fastest rate of solvolysis reaction ?
Cl Cl
Cl Cl
(a) (b) (c) (d)
15. The total number of 2° carbon in the following compound is :
C C C
(a) 20 (b) 21 (c) 23 (d) 24
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ANSWER KEY
6. (?) 12. (d)
1 (a)
7. (a) 13. (b)
2. (?)
8. (d) 14. (a)
3. (?)
9. (c) 15.(b)
4. (b)
5. (?) 10. (b)
11. (a)
HINTS & SOLUTIONS
1. A-Aromatic. The -electron system perpendicular to the ring contians 14 electron (2 for each
triple bond) & should be aromatic. There are no serious geometric or steric constraints to planar-
ity.
C = S can be considered as C = C replacement and the given system is an Azulene analog.
The correct option is (a).
2. The anion of A has an identical reasonance structure, and both are cyclopentadienile - like,
suggesting good stabilisation of the anion. The fused structure in each case is a [10] annulene.
On the other hand, delocalised structures of the anion of B do not indicate complete a delocalisation
of charge. The fused structures are of the hepta fulvene system type.
3. The anion of A has an identical reasonance structure, and both are cyclopentadienile - like,
suggesting good stabilisation of the anion. The fused structure in each case is a [10] annulene.
On the other hand, delocalised structures of the anion of B do not indicate complete a delocalisation
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of charge. The fused structures are of the hepta fulvene system type.
The correct option is (a).
The correct option is (a).
Homo aromatic
H
H
3. 6- planar
Ilomo-Aromatic
4-Planar
Anti-aromatic
2-Planar
Aromatic
The correct option (a).
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4.
both rings Aromatic
The correct option is (b).
5. More acidic strength of compound less will be pKa value
H
O CN H
CN
CN
N H
H
CN
O CN
X Y Z
‘Y’ is most acidic due to presence of strong electron withdrawing and to gain aromatic character.
So, it has least pKa value. ‘Z’ is least acidic, due to Annelation effect of two Benezene ring so. It
has highest pKa value therefore order of pKa value Z > X > Y.
The correct Option is (c).
6. (i) +2K
10 e–system (Aromatic)
(ii) +H2SO4 H
H
Homoaromatic
Heat
(iii)
Electrocyclic Non-aromatic
ring opening
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heat
+2K
(iv)
Anti-aromatic
The correct option is (a)
7. The ring (A) is fused to 2 Benzene rings in such a way that no canonical forms can be written in
which both benzene rings have 6e However in Ring (B) due to the annelation effect reduces
the aromaticity of the ring.
Option option is (a).
8.
O sp3-Hybridised
(Non-aromatic)
Correct option is (d).
H H
(A) (B)
N N N N
9.
N N N N
(D) (C)
In case of Nitrogen-(C) the electron density is more. Hence rate of protonation is fastest with
nitrogen -(c)
Correct option is (C).
10. e Anti-aromatic
Option (b) is correct.
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11. e Anti-amomatic
Option (a) is correct.
12. Azulene has very high dipole moment as compound to nepthalene; phenanthrene and an-
thracene.
Option (d) is correct.
13.
H
–H
Hydride
abstraction (Aromatic)
(Aropylium ion)
Option (b) is correct.
Cl
H 2O Aromatic stabilised carbocation
(Very f ast rate of reaction)
H 2O
14. OH
Correct option is (a).
15. 2 19
3 1 20 18
4 17
21
5 C C C 16
6 15
7 14
8 10 11 13
9 12
Total 21 carbons are there which 2°.
Option (b) is correct.
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