The aldehyde shown is heated with concentrated NaOH. Which outcome is correct?

AAn aldol addition product forms
BOnly the carboxylate salt forms
CEquimolar alcohol and carboxylate salt by the Cannizzaro reaction
DNo reaction occurs because of steric hindrance

Answer: C

The drawn compound is 2,2-dimethylpropanal (pivalaldehyde). Its alpha carbon is quaternary, so there is no alpha-hydrogen and no aldol is possible. It undergoes Cannizzaro disproportionation to neopentyl alcohol and sodium pivalate in equal amounts.

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