JEE Main 2022 · 25 Jun · Shift 1 · Chemistry Q76

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ChemistrySingle correct+4 / -1Question 76 of 90

The intermediate X, in the reaction :

CHCl3 + aqueous NaOH + phenol gives [X]; X with (1) NaOH, (2) H+ gives salicylaldehyde (2-hydroxybenzaldehyde).

2-(trichloromethyl)phenol

2-(dichloromethyl)phenol

sodium 2-(dichloromethyl)phenoxide

sodium 2-(trichloromethyl)phenoxide

Answer and worked solution

Official answer: C

Reimer-Tiemann. Dichlorocarbene from $\mathrm{CHCl_3/NaOH}$ attacks the ortho carbon of the phenoxide, giving the benzal chloride intermediate, sodium 2-(dichloromethyl)phenoxide. Alkaline hydrolysis and acidification turn $\mathrm{CHCl_2}$ into CHO: salicylaldehyde.

(C)

Topics:Phenols Named reactions

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JEE Main 2022 · 25 Jun · Shift 1, Chemistry question 76