1. Tardigrade
  2. Question
  3. Chemistry
  4. p -cresol reacts with chloroform in alkaline medium to give the compound A which adds hydrogen cyanide to form, the compound B. The latter on acidic hydrolysis gives chiral carboxylic acid. The structure of the carboxylic acid is

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Q. $p$ -cresol reacts with chloroform in alkaline medium to give the compound $A$ which adds hydrogen cyanide to form, the compound $B$. The latter on acidic hydrolysis gives chiral carboxylic acid. The structure of the carboxylic acid is

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Solution:

Given that:
$pCH _{3} C _{6} H _{5} OH + CHCl _{3}+ NaOH \rightarrow A \xrightarrow{ HCN }B \xrightarrow{ H ^{+}/ H _{2} O } RCOOH$ (Chiralacid)
The reaction of phenol derivative with chloroform in alkaline medium is ReimerTiemann reaction that gives $CHO$ group at ortho to $Oh$ on the benzene ring. Thus $A = pCH _{3}( o - CHO ) C _{6} H _{3} OH$
Addition of HCN at aldehyde group will result in cyanohydrin formation as: $B = pCH _{3}( o - CH ( CN )( OH )) C _{6} H _{3} OH$
Upon hydrolysis, the cyanide group will give $COOH$ group as $= pCH _{3}( o -$ $\left.C ^{*} H ( COOH )( OH )\right) C _{6} H _{3} OH$
The overall reaction is represented in the figure.

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