Aldehydes, without alpha hydrogens, give the Cannizzaro reaction on treatment with a strong base (NaOH)

cannizzaro

In this reaction one molecule is reduced to alcohol, while the other is oxidized to carboxylic acid.

 

Mechanism:

Stage 1. Addition of the hydroxide ion to the carbonyl

cannizzaro mechanism 01

 

Stage 2. Hydride transfer

cannizzaro mechanism 02

 

Stage 3. Acid-base balance

cannizzaro mechanism 03