JEE Main 2022 · 29 Jun · Shift 1 · Chemistry Q74 · Dronacharya Exams

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ChemistrySingle correct+4 / -1Question 74 of 90

In the given conversion the compound A is :

2-Bromophenol treated with (CH3)3CLi gives [A], which with (i) CO2, (ii) H3O+ gives salicylic acid (2-hydroxybenzoic acid).

A

2-Lithiophenol

Benzene ring with Li and OH on adjacent carbons.

B

Lithium 2-lithiophenoxide

Benzene ring with Li and OLi on adjacent carbons.

C

2-Bromophenyl tert-butyl ether

Benzene ring with Br and OC(CH3)3 on adjacent carbons.

D

2-tert-Butylphenol

Benzene ring with C(CH3)3 and OH on adjacent carbons.

Answer and worked solution

Official answer: B

tert-Butyllithium removes the phenolic H and exchanges Br for Li, giving the dilithio species; $\mathrm{CO_2}$ then acid gives salicylic acid.

(B)

Topics:Carboxylic acids Phenols

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