JEE Main · 2024 · 29 Jan 2024 · Shift 1 · Alcohols Phenols and Ethers

The major product (P) in the following reaction is

(A)(see structure)
(B)(see structure)
(C)(see structure)
(D)(see structure)
✓ Correct

Answer: (D)

Solution

The substrate carries both an ethoxy group (

- OCH_{2} CH_{3}

) and a vinyl group (

- CH = CH_{2}

) on the ring, treated with excess conc. HBr.

Alkyl aryl ethers are cleaved by HX through an

S_{N} 2

attack of

Br^{-}

on the alkyl carbon: the aryl-O bond resists cleavage because of its partial double-bond character from conjugation with the ring. This releases the phenol and ethyl bromide.

Separately, the alkene undergoes Markovnikov addition of HBr.

Together these two transformations on the excess-HBr treatment give product P as option D.

Key confirmed: D.

JEE Main · 2024 · 29 Jan 2024 · Shift 1 · Single correct option

Practise more: all JEE Main PYQs on Alcohols Phenols and Ethers →

More JEE Main questions on Alcohols Phenols and Ethers

Given below are two statements :

Statement I: Phenol on treatment with $CHCl_{3} /$ aq. KOH under refluxing condition, followed by acidification produces $p$ -hydroxy benzladehyde as the major product and $o$ -hydroxy benzaldehyde as the minor product.

Statement II …
JEE Main 2026View solution →
3,3-Dimethyl-2-butanol cannot be prepared by:
A.
B.
C.
D.
E.
Choose the correct answer from the options given below:
JEE Main 2026View solution →
A mixed ether ( P ), when heated with excess of hot concentrated hydrogen iodide produces two different alkyl iodides which when treated with aq. NaOH give compounds (Q) and (R). Both (Q) and (R) give yellow precipitate with NaOI. Identify the mixed ether (P):
JEE Main 2026View solution →
Consider the following two reactions A and B .
(A) (see structure)
(B) (see structure)

Numerical value of [molar mass of $x +$ molar mass of y ] is ______。
JEE Main 2026View solution →
From the following, how many compounds contain at least one secondary alcohol?
JEE Main 2026View solution →
Consider the following reaction sequence

vapour density 47]
Compound (y) develops characteristic colour with neutral $FeCl_{3}$ solution.
Identify the INCORRECT statement from the following for the above sequence.
JEE Main 2026View solution →