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Aromatic Compounds(Practice Problems)IIT 2021-22

1. Which of the following is most reactive towards 13. The compound (X) is
electrophilic substitution reaction?

(a) BrCH2 COOH (b) OHC – COOH

(c) CH3COOH (d) (CH 3CO)2O
2. Which of the following is not aromatic? 14. In the given reactions, X and Y are
(a) Cyclopentadienyl anion (b) Cyclopropenyl cation
(c) Tropylium cation (d) Cyclopentadienyl cation
3. In which of the following cases, the nitration will take
place at meta position
(a) X = bromobenzene, Y = acetophenone
(b) X = o- & p-bromophenol, Y = salicylaldehyde
(c) X = p-bromophenol, Y = salicylic acid
(d) X = o-bromophenol, Y = benzoic acid
(a) II and IV (b) I, II and III 15. Which of the following does not give benzoic acid on
(c) II and III only (d) I only hydrolysis?
4. Which of the following sequence of reagents can be (a) Phenyl cyanide (b) benzoyl chloride
used for the conversion of C6H5CH2CH3 to C6H5CH= CH2 (c) benzyl chloride (d) methyl benzoate
(a) SOCl2; H2O (b) SO2Cl2, alc. KOH 16. In the reaction, the products are
(c) Cl2/hv; H2O (d) SOCl2; alc. KOH
5. Which of following does not undergo Friedel-Crafts
reaction?
(a) aniline (b) phenol
(c) nitrobenzene (d) all
6. Structure of the major product in the following reaction is

17. Anisole on reaction with chloromethane in presence of

anhydrous AlCl3 gives
(a) o-methyl anisole and p-methyl anisole
(b) p-methyl anisole and p-methoxy anisole
(c) o-ethyl anisole and p-methyl anisole
(d) p-methoxy acetophenone and p-methoxy
7. Phenol can be distinguished from ethanol by the acetophenone
following reagents except 18. Benzaldehyde differs from acetaldehyde in the
(a) Na b) phthalic anhydride/conc. H2SO4 &NaOH condition
(c) neutral FeCl3 (d) Br2/H2O (I) benzaldehyde does not react with Tollen’s reagent
8. Which of the following statements is incorrect? (ii) benzaldehyde does not react with Fehling solution
(a) Decreasing order of acidic character of nitrophenols is (iii) benzaldehyde does not react with HCN
p-O2NC6H4OH > o-O2NC6H4OH > m-O2NC6H4OH. (iv) benzaldehyde does not react with NaHSO3
(b) Decreasing order of acidic character of chlorophenols (a) i, iv (b) ii, (c) ii, iv (d) i, ii, iii
is o-C1C6H4OH > m-C1C6H4OH >p-C1C6H4OH 19. Which of the following has lowest pKa value?
(c) meta-Cresol is a weaker acid than ortho or para-cresol.
(d) All correct.
9. What amount of bromine will be required to convert 2g
of phenol into 2,4,6-tribromophenol?
(a) 20.44 g (b) 6.00 g
c) 4.00 g (d) 10.22 g
10. The major product obtained on the monobromination 20.The correct decreasing order of basicity of the
(with Br2/FeBr3) of the following compound ‘A’ is following compounds is

(a) I>II>III>IV (b) II>I>IIII>IV

(c) III>IV>I>II (d) II>I>IV>III
21. Which of the following is more basic than aniline?
(a) benzylamine (b) Diphenylamine
(c) Triphenylamine (d) p-Nitroaniline
11. Product of this reaction will be 22. I n order to di stingui sh bet ween C 2 H 5 NH 2 and
C 6 H 5 NH 2 , which of the following reagent(s) is useful?
(a) Hinsberg reagent (b) -naphthol
(c) CHC13/KOH (d) NaOH
23. Product C of this reaction is

12. Which of the following compounds will give tribromo-

derivative on treatment with bromine water?

24. Which of the following is [8] annulene ?

(a) Benzene (b) Cyclooctatetraene
(c) Cyclobutadiene (d) None of these
25. Which of the following is antiaromatic compound 34. Nitration of which of the following reactant gives
(a) Cyclobutadiene (b) Cyclooctatetraenyl dianion maximum % of meta product (using HNO3/H2SO4)?
(c) Cyclopropenylcation (d) Benzene (a) Toulene (b) Aniline
26. Which of the following alcohols would you expect to (c) Benzene (d) Isopropyl benzene
form a carbocation most readily in sulphuric acid? 35. The product (Y) of the following sequence of reactions
would be:

27. Which of the following will accept H+ ion with fastest

rate?

36. On hydrolysis in aqueous acetone the given

compound gives

28. Which of the following compounds is most stable.

29. Compound X (C10H6) liberates 2 moles of CH4 when

treated with methyl magnesium bromide. On heating with
KMnO4 solution, X produces benzene dicarboxylic acid
which on mononitration produces only one product and no
other isomers. A can be:
(a) A and B (b) only A (c) B and C(d) only C
37. Compound A, C14H12, could be hydrogenated to B
(C14H14) using 1 atm of H2 at 25°C over Pt. Treatment of A
or B with hot KMnO4/H2O lead to benzoic acid as the only
isolable product similarly ozonolysis of A, followed by
reductive work up give only benzaldehyde. What is A?

30.The product of the following reaction is

38. In the following reaction, which of the following

products is not formed at all?

31. Nitration of the following compound

39. Which of the following substituted benzene derivatives

would furnish three isomers when one more substituent is
introduced

(a) (b) (c) (d) all

Passage
32. The compound (E) in the given reaction is:

40 ‘N’ is

33. Compound X (C8H8O3) gives coloured precipitate with

FeCl3 and shining black deposit on reaction with 41. ‘O’ is
AgNO3/NH4OH solution. It gives no turbidity with
ZnCl2/HCl. On bromination, it gives only monobrominated
product. Its structural formula can be:

IIT-2