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  4. Which one of the following on treatment with 50 % aqueous sodium hydroxide yields the corresponding alcohol and acid?

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Q. Which one of the following on treatment with $50\%$ aqueous sodium hydroxide yields the corresponding alcohol and acid?

AIPMTAIPMT 2007Aldehydes Ketones and Carboxylic Acids

Solution:

Aldehydes which do not have any $\alpha$-hydrogen atom when heated with a concentrated solution of $NaOH$ undergo a simultaneous oxidation and reduction (disproportionation) forming a salt of carboxylic acid and alcohol. This reaction is called Cannizaro reaction.
$2 C _{6} H _{5} CHO + NaOH \longrightarrow \underset{\text{Benzyl alcohol}}{ C _{6} H _{5} CH _{2} OH } + \underset{\text{Sodium benzoate}}{C _{6} H _{5} COONa}$