CSIR-NET, SET

JAM

IIT - GATE,
ASSIGNMENT
AROMATICITY

1. Among the carbonations given below

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 homoaromatic.
d) A is homoaromatic, B is aromatic and C is antiaromatic.
2. The correct order of acidity of the following compound A C is:

B>C>A

b) C > B > A

c) A > C > B

d) A > B > C

3. Among A C, the aromatic compounds are

A, B and C

c) B and C only

A and B only

d) A and C only

H.O:- 28A/11, Ist Floor, Jia Sarai, Hauz Khas, Near IIT Delhi-16
Phone No.-011-69000403, 9810236711 -09599967768
www.chemistrydias.com

CSIR-NET, SET
JAM

IIT - GATE,

4. The correct order of acidity of the compounds A C is

A>B>C

c) C > A > B

B>C>A

d) B > A > C

5. Among the following compounds, the one which has highest dipole moment is

6. Amongst the following, the compound which has the lowest energy barrier for the cistrans isomerization is

7. The compound that is antiaromatic is

b) II

c) III

H.O:- 28A/11, Ist Floor, Jia Sarai, Hauz Khas, Near IIT Delhi-16
Phone No.-011-69000403, 9810236711 -09599967768
www.chemistrydias.com

d) IV

CSIR-NET, SET
JAM

IIT - GATE,

8. The compound that gives precipitate on warming with aqueous AgNO3 is

9. Among the following compounds, the one that is non- aromatic, is

10. Shown below is a Hammett plot obtained for the reaction.

H.O:- 28A/11, Ist Floor, Jia Sarai, Hauz Khas, Near IIT Delhi-16
Phone No.-011-69000403, 9810236711 -09599967768
www.chemistrydias.com

CSIR-NET, SET
JAM

IIT - GATE,

The change in slope of the plot indicates that

a

The reaction does not follow linear free energy relationship

Electrons are being withdrawn from the transition state in the mechanism

Electrons are being donated to the transition state in the mechanism

The mechanism of the reaction is changing

11. The decreasing order of acidity of the marked H of the following molecules is

I > II > III

c) III > I > II

III > II > I

d) II > I > III

12. The compound

is.

Aromatic and has high dipole moment

Aromatic and has no dipole moment

Non-aromatic and has high dipole moment

Anti-aromatic and has no dipole moment.

H.O:- 28A/11, Ist Floor, Jia Sarai, Hauz Khas, Near IIT Delhi-16
Phone No.-011-69000403, 9810236711 -09599967768
www.chemistrydias.com

CSIR-NET, SET
JAM

IIT - GATE,

13. The compound that is NOT aromatic is

14. The most acidic species is

15. The Hammett reaction constant

is based on

The rates of alkaline hydrolysis of substituted ethyl benzoates.

The dissociation constants of substituted acetic acids

The dissociation constants of substituted benzoic acids

The dissociation constants of substituted phenols

16. Match the reactions of some p substituted benzene derivatives (a) (b) given in List
I with the Hammetts p values (i) (iv) I List II and identity the correct match.
List I

A. ArCH 2 Cl

aq .acetone
700 C

ArCH
2 OH

HCl

H O
ArCH 2 COO H
B. ArCH 2 CO2 H 252C
0

C. Ar Cl
MeONa
/ MeOH Ar OMe Cl
500 C
H O
D. Ar CO2 H 2520C Ar COO H

List II
i) + 8.50
ii) +1
iii) + 0.49
iv) 1.88
a

A - i, B iv, C-iii, D-ii

H.O:- 28A/11, Ist Floor, Jia Sarai, Hauz Khas, Near IIT Delhi-16
Phone No.-011-69000403, 9810236711 -09599967768
www.chemistrydias.com

CSIR-NET, SET
JAM
b

A-iv, B-i, C-ii, D-iii

A-I, B-ii, C-iv, D-iii

A-iv, B-iii, C-I, D-ii

IIT - GATE,

17. Among the resonance forms given below, the one which contributes most to the
stability of Azulene is.

18. The following hydrocarbon has a dipole moment of 0.8 D because.

It exists as

in which both the rings exhibit aromaticity

e) Charge separation permits conformational stability

f) The two rings are of different size
g) The molecule obeys 4n +2 huckel rule
19. Azulene possesses a dipole moment because of:
a

Aromaticity

c) Planarity

h) Anti aromatcity

d) Diradical Character

20. Which of the following compounds would be not be considered aromatic in its
behaviour?

b) B

c) C

st

H.O:- 28A/11, I Floor, Jia Sarai, Hauz Khas, Near IIT Delhi-16
Phone No.-011-69000403, 9810236711 -09599967768
www.chemistrydias.com

d) D

CSIR-NET, SET
JAM

IIT - GATE,

21. Which one of the following statements is TRUE.

PhLi adds to both compounds with equal case

PhLi does not add to either of the compounds

PhLi reacts readily with 1 but does not add to 2

PhLi reacts readily with 2 but does not add to 1

22. Of the following molecular species, this is expected to shown the greatest stability.

23. Which of the following compounds is aromatic?

24. This of the following compounds will precipitate of AgBr.

I, II, III

c) II and III only.

I and II only.

d) I and III only.

H.O:- 28A/11, Ist Floor, Jia Sarai, Hauz Khas, Near IIT Delhi-16
Phone No.-011-69000403, 9810236711 -09599967768
www.chemistrydias.com

CSIR-NET, SET
JAM

IIT - GATE,

25.

The Compound (D) is

H.O:- 28A/11, Ist Floor, Jia Sarai, Hauz Khas, Near IIT Delhi-16
Phone No.-011-69000403, 9810236711 -09599967768
www.chemistrydias.com