JEE Main · 2024 · 06 Apr 2024 · Shift 2 · Haloalkanes and Haloarenes

Consider the above chemical reaction. Product " A " is:

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

Answer: (B)

Solution

The chlorinated substrate reacts with aqueous NaOH by an

S_{N} 1

pathway: ionisation of the C–Cl bond gives a carbocation, which undergoes a 1,2-hydride shift to the more stable (more substituted) carbocation before hydroxide traps it. The major product therefore carries

- OH

at the rearranged position rather than at the original C–Cl carbon, matching Allen's option (2).

JEE Main · 2024 · 06 Apr 2024 · Shift 2 · Single correct option

Practise more: all JEE Main PYQs on Haloalkanes and Haloarenes →

More JEE Main questions on Haloalkanes and Haloarenes

The correct order of reactivity of $CH_{3} Br$ in methanol with the following nucleophiles is $F^{-}, I^{-}, C_{2} H_{5} O^{-}$ and $C_{6} H_{5} O^{-}$
JEE Main 2026View solution →
The correct order of the rate of reaction of the following reactants with nucleophile by $S_{N} 1$ mechanism is :
(Given : Structure I and II are rigid)
JEE Main 2026View solution →
The correct order of reactivity of the following benzyl halides towards reaction with KCN is:
JEE Main 2026View solution →
The correct order of the rate of the reaction for the following reaction with respect to nucleophiles is:
$CH_{3} Br + Nu^{Θ} ⟶ CH_{3} Nu + Br^{Θ}$
JEE Main 2026View solution →
Given below are four compounds:
(a) n-propyl chloride
(b) iso-propyl chloride
(c) sec-butyl chloride
(d) neo-pentyl chloride

Percentage of carbon in the one which exhibits optical isomerism is:
JEE Main 2026View solution →
Consider the following reaction :

$(i) NaNH_{2} (ii) ↓ - Br Y$

The product Y formed is :
JEE Main 2026View solution →