Question

Which of the following compounds would undergo aldol condensation, which undergoe Cannizzaro reaction and which neither? Write the structures of the expected products of aldol condensation and Cannizzaro reaction.
(i) Methanal (ii) 2-Methylpentanal (iii) Benzaldehyde
(iv) Benzophenone (v) Cyclohexanone (vi) 1-Phenylpropanone
(vii) Phenylacetaldehyde (viii) Butan-1-ol (ix) 2,2-Dimethylbutanal

Answer 1

Compounds (ii), (v), (vi), (vii): undergo aldol condensation as they have alpha hydrogen atom. Compounds (i), (iii), (ix) undergo Cannizaro reaction as they do not have alpha H atoms. Compounds (iv), (viii) show neither reaction. The structures of expected products are as shown.