Alcohols Phenols and Ethers JEE Main PYQs (2020–2026)

Solved Alcohols Phenols and Ethers PYQs

3 recent questions with answers. The full set of 136 is free to practise.

1. JEE Main 2025EasyClassification, Nomenclature and Physical Properties of Alcohols, Phenols and Ethers
   Q1

   Given below are two statements :
   
   Statement I : Dimethyl ether is completely soluble in water. However, diethyl ether is soluble in water to a very small extent.
   
   Statement II : Sodium metal can be used to dry diethyl ether and not ethyl alcohol.
   
   In the light of given statements. choose the correct answer from the options given below

   • AStatement I is false but Statement II are true
   • BStatement I is true but Statement II is false
   • CBoth Statement I and Statement II are true
   • DBoth Statement I and Statement II are False

   Show answer & solution

   Correct answer: (C)

   St-I - St-I is correct because both given ether are soluble in water $\to$ Di ethyl ether and butan-1-ol are miscible to almost same extent i.e., 7.5 and 9 gm per 100 ml water due to H -bonding
   
   St-II : - St. II is also correct because sodium metal is not used with ethyl alcohol as $H_2$ gas release with ethyl a below
2. JEE Main 2024EasyReactions of Phenols
   Q2

   Given below are two statements: One is labelled as Assertion A and the other is labelled as Reason R:
   
   Assertion A: ${pK}_a$ value of phenol is 10.0 while that of ethanol is 15.9 .
   
   Reason R: Ethanol is stronger acid than phenol.
   
   In the light of the above statements, choose the correct answer from the options given below:

   • AA is false but R is true.
   • BBoth $A$ and $R$ are true but $R$ is NOT the correct explanation of $A$ .
   • CBoth $A$ and $R$ are true and $R$ is the correct explanation of $A$ .
   • D$A$ is true but $R$ is false.

   Show answer & solution

   Correct answer: (D)

   Phenol is more acidic than ethanol because conjugate base of phenoxide is more stable than ethoxide.
3. JEE Main 2023HardPreparation of Ethers
   Q3

   2-Methyl propyl bromide reacts with $C_2{H}_5{O}^{-}$ and gives ‘A’ whereas on reaction with $C_2{H}_{5}OH$ it gives ‘B’. The mechanism followed in these reactions and the products ‘A’ and ‘B’ respectively are :

   • A$S_{N}1,A=$ tert-butyl ethyl ether; $S_{N}2,B=$ iso-butyl ethyl ether
   • B$S_{N}1,A=$ tert-butyl ethyl ether; $S_{N}1,B=$ 2-butyl ethyl ether
   • C$S_{N}2,A=$ iso-butyl ethyl ether; $S_{N}1,B=$ tert-butyl ethyl ether
   • D$S_{N}2,A=$ 2-butyl ethyl ether; $S_{N}2,B=$ iso-butyl ethyl ether

   Show answer & solution

   Correct answer: (C)

   2-Methyl propyl bromide (also known as isobutyl bromide) has the formula (CH₃)₂CHCH₂Br.
   
   it reacts with C₂H₅O^- (ethoxide ion), it undergoes an SN2 reaction because ethoxide ion is a strong nucleophile. The reaction proceeds with a direct exchange of the leaving group (Br^-) and the nucleophile (C₂H₅O^-). The product ‘A’ would be iso-butyl ethyl ether (CH₃CH₂OCH(CH₃)CH₃).
   
   it reacts with C₂H₅OH (ethanol), the reaction proceeds via an SN1 mechanism because ethanol is a weak nucleophile. In this case, the bromide ion leaves first, forming a carbocation intermediate, which is then attacked by the nucleophile (C₂H₅OH). The product ‘B’ would be tert-butyl ethyl ether ((CH₃)₃COCH₂CH₃).
   
   , the correct option is:
   
   N2, A = iso-butyl ethyl ether; SN1, B = tert-butyl ethyl ether

Topic-wise question count

Where JEE Main has asked from Alcohols Phenols and Ethers, most frequent first.

• Reactions of Phenols43
• Reactions of Alcohols31
• Reactions of Ethers19
• Preparation of Alcohols19
• Classification, Nomenclature and Physical Properties of Alcohols, Phenols and Ethers12
• Preparation of Phenols6
• Preparation of Ethers6

Year-wise Alcohols Phenols and Ethers questions in JEE Main

Number of questions from this chapter in each year's paper(s).