JEE Main · 2021 · 27 Aug 2021 · Shift 1 · Haloalkanes and Haloarenes

In the following sequence of reactions the P is:

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

Answer: (D)

Solution

Chlorocyclopentane reacts with magnesium in dry ether to form cyclopentylmagnesium chloride, a Grignard reagent whose ring carbon is strongly nucleophilic and basic. Treated with ethanol, this carbanionic carbon abstracts the acidic

O - H

proton, so the ring carbon gains only a hydrogen rather than an ethyl group or an alkoxy group. The product is cyclopentane.

JEE Main · 2021 · 27 Aug 2021 · Shift 1 · Single correct option

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