(ALCOHOLS, PHENOLS AND ETHERS) PYQ’S FOR JEE MAINS

1. Compound ’ B ’ is [April 11, 2023 (II)]

2. A compound 𝑋 when treated with phthalic anhydride in presence of concentrated H2 SO4 yields Y. Y is
used as an acid/base indicator. ’ X ’ and ’ Y ’ are respectively: [April 08, 2023(II)]
A) Carbolic acid, Phenolphthalein B) Anisole, methyl orange
C) Salicylaldehyde, Phenolphthalein D) Toludine, Phenolphthalein
3. The strongest acid from the following is [April 06, 2023 (II)]

4. Decreasing order of dehydration of the following alcohols is [Feb. 01, 2023 (I)]

A) D > B > C > A B) A > D > B > C C) B > A > D > C D) B > D > C > A
5. An organic compound ’ A ’ with empirical formula C6 H6 O gives sooty flame on burning. Its reaction with
bromine solution in low polarity solvent results in high yield of B. B is [Jan. 31, 2023 (I)]

6. The correct order of pK a values for the following compounds is: [Jan. 30, 2023 (II)]

A) c > a > d > b B) b > d > a > c C) b > a > d > c D) a > b > c > d

7. The increasing order of pK a for the following phenols is [Jan. 29, 2023 (I)]
A) 2,4-Dinitrophenol B) 4 - Nitrophenol C) 2,4,5-Trimethylphenol D) Phenol E) 4-Chlorophenol
9. In the cumene to phenol preparation in presence of air, the intermediate is [Jan. 25, 2023 (I)]

10. A compound ’ X ’ is acidic and soluble in NaOH solution, but insoluble in NaHCO3 solution. Compound X
also gives violet colour ’vith neutral FeCl3 solution. The compound ’ X ’ is : [July 29, 2022 (I)]

11. Identify the major product A and B for the below given reaction sequence. [July 28, 2022 (I)]

12. The difference in the reaction of phenol with bromine in chloroform and in water medium is due to:
A) Hyperconjugation in substrate B) Polarity of solvent [July 26, 2022 (I)]
C) Free radical formation D) Electromeric effect the substrate
13.

Arrange in decreasing acidic strength [July 25,2022]

A) A > B > C > D B) B > A > C > D C) D > C > A > B D) D > C > B > A

14.

Identify the component A and component B: [June30, 2022 (I)]

15. Statement I : Phenols are weakly acidic. [June 29, 2022 (I)]
Statement II : Therefore they are freely soluble in NaOH and are weaker acids than alcohols and water.
A) Both Statement I and Statement II are correct. B) Both Statement I and Statement II are incorrect.
C) Statement I is correct but Statement II is incorrect.D) Statement I is incorrect but Statement II is correct.
16. Match List-I with List-II [June 27, 2022 (II)]

A) A-IV, B-III, C-II, D-I B) A-IV, B-III, C-I, D-II C) A-II, B-III, C-I, D-IV D) A-IV, B-II, C-III, D-I

17. Compound P on nitration with dil. HNO3 yields two isomers (A) and (B). These isomers can be separated by
steam distillation. Isomers (A) and (B) show intramolecular and intermolecular hydrogen bonding
respectively. Compound P on reaction with conc. HNO3 yields a yellow compound 𝐶, a strong acid. The
number of oxygen atoms present in compound C is _____________. [June 26, 2022(I)]

18. Phenol on reaction with dilute nitric acid, gives two products. Which method will be most effective for
large scale separation? [June 25, 2022 (I)]
A) Chromatographic separation B) Fractional Crystallisation C) Steam distillation D) Sublimation
20. The intermediate 𝑋, in the reaction [June 25, 2022 (I)]

21. In the following reaction compounds A and B are respectively [June 25, 2022 (I)]

22. Which of the following conditions or reaction sequence will NOT give acetophenone as the major product?
[June 25, 2022 (II)]

23. The correct structures of A and B formed in the following reactions are : [Aug. 27, 2021 (II)]
24. Which one of the following phenols does not give colour when condensed with phthalic anhydride in
presence of conc. H2 SO4 ? [Aug. 26, 2021 (II)]

25.

Consider the above reaction, and choose the correct statement: [July 27, 2021 (II)]
A) The reaction is not possible in acidic medium B) Both compounds A and B are formed equally
C) Compound A will be the major product D) Compound B will be the major product
26. Reaction of Grignard reagent, C2 H5 MgBr with C8 H8 O followed by hydrolysis gives compound " A "
which reacts instantly with Lucas reagent to give compound B, C10 H13 Cl. [March 18, 𝟐𝟎𝟐𝟏 𝐈 ]

27. Identify A in the given reaction, [Feb. 26, 2021 (II)]

28. A solution of phenol in chloroform when treated with aqueous NaOH gives compound P as a major
product. The mass percentage of carbon in P is_________. (to the nearest integer) [Sep. 06, 2020 (III)]

29.
P gives positive ceric ammonium nitrate test. This is because of which −OH group(s) ? [Sep. 03, 2020 (II)]
A) (ii) only B) (iii) and (iv) C) (iv) only D) (ii) and (iv)
30. The major product of the following reaction is : [Sep. 02, 2020 (II)]

31. Arrange the following compounds in increasing order of C - OH bond length: methanol, phenol,
𝑝-ethoxyphenol [Jan. 08, 2020 (I)]
A) methanol <-ethoxyphenol < phenol B) phenol < methanol < 𝑝-ethoxyphenol
C) phenol < 𝑝-ethoxyphenol < methanol D) methanol < phenol < 𝑝-ethoxyphenol
32. What will be the major product when 𝑚-cresol is reacted with propargyl bromide HC ≡ C − CH2 Br in
presence of K 2 CO3 in acetone? [April 12, 2019 (II)]

33. The major product of the following reaction is : [Jan. 11, 2019 (I)]
34. The major product of the following reaction is :

35. The major product of the following reaction is : [Jan. 11, 2019 (II)]

36. The increasing order of the p𝐾a values of the following compounds is: [Jan. 10, 2019 (I)]

A) C < B < A < D B) B < C < D < A C) D < A < C < B D) B < C < A < D
37. The major product of the following reaction is: [Jan. 10, 2019 (II)]

38. The products in reaction of cumene with O2 followed by treatment with dil. HCl are: [Jan. 9, 2019 (II)]

39. Phenol with CO2 in presence of NaOH followed by acidification produces X as the major product. X with
CH3 CO 2 O in the presence of catalytic amount of H2 SO4 produces: [2018; Similar 2014]
40. Phenol reacts with methyl chloroformate in the presence of NaOH to form product A. A reacts with Br2 to
form product B. A and B are respectively : [2018]

41. Which of the following, upon treatment with tert-BuONa followed by addition of bromine water, fails to
decolourize the colour of bromine? [2017]

42. The major product of the following reaction is : [Online April 8, 2017]

43. The following reaction

is known as: [Online April 11, 2014]

A) Perkin reaction B) Gatterman-Koch Formylation C) Kolbe’s reaction D) Gattermann reaction
44. Which one of the following substituents at para-position is most effective in stabilizing the

phenoxide ion? [Online April 19, 2014]

A) −CH3 B) −OCH3 C) −COCH3 D) −CH2 OH

45. Which one of the following will not be soluble in sodium bicarbonate? [Online April 19, 2014]
A) 2,4,6-Trinitrophenol B) Benzoic acid C) 𝑜-Nitrophenol D) Benzene sulphonic acid
46. Arrange the following compounds in order of decreasing acidity : [2013; Similar 2011]

A) II > IV > I > III B) I > II > III > IV C) III > I > II > IV D) IV > III > I > II
47. What is the major product when phenol is treated with bromine water? [Online April 22, 2013]

48. The reaction of phenol with benzoyl chloride to give phenyl benzoate is known as: [Online April 23, 2013]
A) Claisen reaction B) Schotten-Baumann reaction
C) Reimer-Tiemann reaction D) Gatterman-Koch reaction
49. The major product in the following reaction is: [Online April 25, 2013]

50. Phenol with CHCl3 and NaOH gives salicylaldehyde. The reaction is called: [Online April 25, 2013]
A) Reimer-Tiemann reaction B) Claisen reaction C) Cannizzaro’s reaction D)Hell-Volhard-Zelinsky reaction

51. Consider the reaction: C2 H5 OH + H2 SO4 → Product

Among the following, which one cannot be formed as a product under any conditions ? [2011]
A) Ethylene B) Acetylene C) Diethyl ether D) Ethylhydrogen sulphate
52. Phenol, when it reacts first with conc. sulphuric acid and then with conc. nitric acid, gives [2008]
A) 2,4,6-trinitrobenzene B) o-nitrophenol C) p-nitrophenol D) nitrobenzene
53. The compound that gives a tribromo derivative on treatment with bromine water is [2006]

54.

Electrophile in the reaction is [2006]

⊖
A) trichloromethyl anion CCl3 B) formyl cation C) phenoxide ion D) dichlorocarbene
55. Picric acid is: [2002]