JEE Main Chemistry question

[IIT 1995] When phenol is reacted with CHCl₃ and NaOH, followed by acidification, salicylaldehyde is obtained. Which species are involved as intermediates in this reaction?

(A)A dichlorocarbene-addition (*ortho*) intermediate
(B)A benzylic *gem*-dichloride intermediate
(C)Both (A) and (B), formed sequentiallyCorrect
(D)Neither of these

Answer: (C)

Solution

In the Reimer–Tiemann mechanism, NaOH first generates dichlorocarbene (:CCl₂) from CHCl₃; this electrophilic carbene adds to the *ortho* position of the phenoxide ion, giving a

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Question ID VK-140102