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  4. When phenol is reacted with CHCl3 and NaOH followed by acidification, salicylaldehyde is obtained. How many among following species are involved in the above mentioned reaction as intermediates? <img class=img-fluid question-image alt=image src=https://cdn.tardigrade.in/img/question/chemistry/00af06351c6471e0b779b5b2f43eb5f3-.png />

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Q. When phenol is reacted with $CHCl_{3}$ and $NaOH$ followed by acidification, salicylaldehyde is obtained. How many among following species are involved in the above mentioned reaction as intermediates?
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Alcohols Phenols and Ethers

Solution:

The given reaction involves electrophilic substitution on the highly reactive phenoxide ion
Here the electrophile is dichlorocarbene formed by the action of strong alkali on chloroform
$CHCl_{3} +OH^{-} \rightleftharpoons CCl^{-}_{3}+H_{2}O$
$: CCl^{-}_{3} \rightleftharpoons \underset{\text{Dichlorocarbene}}{:CCl_{2}}+Cl^{-}$
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