Exam Blog › Why students lose marks on Cannizzaro reaction questions

Why students lose marks on Cannizzaro reaction questions

Most Cannizzaro mistakes come down to one thing: forgetting to check for alpha-hydrogens before picking a mechanism.

Mistake 1: applying Cannizzaro to an aldehyde that has alpha-hydrogens

CH3CHO→conc. NaOHAldol, not Cannizzaro\text{CH}_3\text{CHO} \xrightarrow{\text{conc. NaOH}} \text{Aldol, not Cannizzaro}

If the aldehyde has even one alpha-hydrogen, it will follow the aldol pathway under basic conditions instead — Cannizzaro only applies to aldehydes like HCHO\text{HCHO}, C6H5CHO\text{C}_6\text{H}_5\text{CHO}, and (CH3)3C-CHO(\text{CH}_3)_3\text{C-CHO} that have none.

Mistake 2: writing the wrong pair of products

Cannizzaro is a disproportionation — one molecule is reduced, one is oxidized. Half the marks lost here come from writing only the alcohol or only the salt, not both.

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