AROMATIC COMPOUNDS Page # 41

Exercise - VI JEE-Problems

1. State the conditions under which the follow- 11. Answer the following with suitable equation
ing preparationis carried out “Aniline from wherever necessary [JEE 1987]
benzene” [JEE 1983] (i) How can you prepare benzene from lime?
(ii) How will convert toluene to m- nitrobenzoic
acid ?
2. Give reasons for the following in one or two
sentences “Althrough benzene is highy 12. Arrange the following in increasing order of re-
unsturated, normally it does not undergo ad- activity towards sulphonation with fuming
dition reaction.” [JEE 1983] sulphuric acid Benzene, toluene, methoxy ben-
zene, chlorobenzene. [JEE 1988]
3. Write down the reaction involved in the prepa-
ration of following using the reagents indicated 13. How will you bring about the following conver-
against in parentheis Ethyl benzene from ben- sion ? “4- nitro aniline to 1,2,3-tribromo ben-
zene” [C2H5OH,PCl5, anhyd. AlCl3] zene”. [JEE 1990]
[JEE 1984]
14. Given reasons in two or three sentences only
4. How many sigma and pi-bonds are present in
for the following: [JEE 1992]
a benzene molecule? [JEE 1985]
Phenyl group is known to exert negative in-
ductive effect, but each phenyl ring in biphe-
5. How would you convert aniline into chloroben- nyl (C6H5 – C6H5) is more reactive than ben-
zene? zene towards electrophilic substitution.
[JEE 1985]
15. The structure of the intermediate product
6. Write down the main product of the following formed by the oxidation of toluene with CrO3
and acetic anhydride whose hydrolysis gives
reaction Benzene CH
3CH
2COCl
 / AlCl3
 benzaldehyde is .........[JEE 1992]
[JEE 1985]

7. Give reason in one or two sentences for the

following “o-nitrophenol is steam volatile 16. + (CH3)2CH.CH2Cl
whereas p - nitorphenol is not” [JEE 1985]

8. A compound of molecular formula C7H8O is in AlCl

 3  (1)
insoluble in water and dilute sodium bicarbon- [JEE 1992]
ate but dissolve in dilute NaOH solution and
gives a characteristic colour with FeCl3. On 17. Outline a synthesis of p-bromonitrobenzene
treatment with bromine water it readily gives from benzene in two steps.[JEE 1993]
a precipitate of C7H5OBr3. Write down the
structure of the compound.
18. ldentify the major product in the following re-
[JEE 1985]
actions : [JEE 1993]
9. Explain the followings in one or two sentences
only: HNO 3(H 2SO 4)
COO
Phenol is an acid but it does not react with mononitration
sodium bicarbonate. [JEE 1987]

10. Complete the following with appropriate struc- 19. Given reason for the following
tures: [JEE 1986] [JEE 1994]

OH OH “ln acylium ion the structure R – C  O is
CHO +
more stable then R—C=O ”
? (1)
(B)
(C)
(D)

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 Page # 42 AROMATIC COMPOUNDSE

20. Predict the major product in the following re-

actions [JEE 1994]
OMe

(i) + (CH3)2 CHCH2OH H

2SO 4

+

C2H5

(ii) (
i ) Br , heat , light
 
( ii ) NaCN (
i ) AlCl3
 Zn ( Hg ) / HCl
 A   
( ii ) H 3O

O
21. How will you bring about the following conver-
sions ? “4 nitobenzaldehyde from benzene”. Meo
[JEE 1994] H3PO4
B
22. How will you bring about the following conver-
sions ? “Benzamide from nitrobenzene”.
[JEE 1994]
27. How will you prepare m-bromoiodobenzene from
23. Complete the follwoing reactions with appro- benzene (in not more than 5-7 steps )?
priate reagents [JEE 1994] [JEE 1996]

28. Complete the following giving the structures

of the principal organic products.
[JEE 1997]
NH – C –
Me CH3

I
H3C C CH2Br Anhy .AlCl 3
+   
NO2
CH3 H
I
29. Following reaction gives two products. Write
the structures of the products.
24. Complete the following with appropriate struc- Br2 / Fe
CH3CONHC6H5   [JEE 1998]
ture: [JEE 1995]
NH2 30. Show the steps to carry out the following
transformations: [JEE 1998]
NO2 (1) Ethylbenzene  benzene
(B) Ethylbenzene  2-phenylpropionic acid
(
i ) NaNO 2 and HCl at 5 C
  A
( ii ) anisole

31. alcoholicK OH , heat

C6H5CH2CHClC6H5 
NO2    (1) + (B)
[JEE 1998]
25. Toluene reacts with bromine in the presence
32. Give reasons for the following in one or two
of light to give benzyl bromine while in pres-
sentences
ence of FeBr3 it gives p-bromotoluene. Give
“Nitrobenzene does not undergo Friedel-Crafts
explanation for the above observations.
alkylation”. [JEE 1998]
[JEE 1996]
33. Write the structures of the products
26. Predict the structures of the intermediates/
[JEE 1998]
products in the following reactions sequences
[JEE 1982] CH3CONHC6H5 Br / Fe
2  

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 AROMATIC COMPOUNDS Page # 43

34. Explain why o hydroxy benzaldehyde is a liquid

at room temperature while p-hydroxy benzal-
dehyde is a high melting solid ?
[JEE 1999] CH2CH2CH3

35. What would be the major product in the fol- Cl

lowing reaction? [JEE 2000]
Cl
2 /
FeCl 3
 A Na
Hg / HCl
 B

F

HNO3/H2SO4

CH 2  HCH 2 ONa , H 2 O
D  C

NaOCH
 3 

H2/Pd/C
E
NO2
41. Carry out the following conversions.
[JEE 2003]
36. How would you bring about the following con-
(i) Phenol to aspirin
version (in 3 steps)? [JEE 2000]
(ii) Benzoic acid to meta - fluorobenzoic acid
in not more than three steps.
Aniline  Benzylamine
42. There is a solution of p-hydroxybenzoic acid
37. What would be the major product in the fol-
and p-amino benzoic acid. Discuss one method
lowing reaction ? [JEE 2000]
by which we can separate them and also write
down the confirmatory test of the functional
group present. [JEE 2003]

43. Which of the following is more acidic and why

N Br
2 / 
Fe (1eq )
 ? [JEE 2004]

+
NH 3
+
38. Give reasons for the following:
NH 3
[JEE 2000]
(i) tert-butylbenzene does not give benzoic
acid on treatment with acidic KMnO4
(ii) Normally benzene gives electrophilic sub-
stitution reaction rather than electrophilic ad-
dition reaction although it has double bond.
F
39. How would you synthesis 4 methoxyphenol (I) (II)
from bromobenzene in NOT more than five
steps? State clearly the reagents used in each 44. Convert
step and show the structures of the interme-
diate compounds in your synthetic scheme. NO2 NO2
[JEE 2001]

40. Write structures of the products A,B,C D and

E in the following scheme
[JEE 2002]
OH
in not more than four steps. Also mention the
reaction conditions and temperature.
[JEE 2004]

394 - Rajeev Gandhi Nagar Kota, Ph. No. 0744-2209671, 93141-87482, 93527-21564
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 Page # 44 AROMATIC COMPOUNDSE

Fill in the blanks

45. In an acidic medium ........ behaves as the
strongest base (Nitrobenzene aniline phenol)
[JEE 1981]

46. The acidity of phenol is due to the ........ of

its anion [JEE 1984]

47. Formation of phenol form chlorobenzene is an

example of ........ aromatic substitution
[JEE 1989]

48. Phenol is acidic due to resonance stabillization

of its conjugate base, namely ........
[JEE 1990]

49. Amongst the three isomers of nitrophenol, the

one that is least soluble in water is ...
[JEE 1990]

50. The high melting point and insolubility in or-

ganic solvents of sulphanilic acid are due to
its ....structure [JEE 1992]

394 - Rajeev Gandhi Nagar Kota, Ph. No. 0744-2209671, 93141-87482, 93527-21564
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