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

Explanation

2-Methylpertfanal, cyclohexanon, 1-phenylpropanone and phenylacetaldehyde contain one or more a-hydrogen and hence undergo aldol condensation. The reactions and the structures of the expected products are given below.

Benzophenone (iv) is a ketone having no `alpha`-hydrogen while butan-l-il (viii) is an alcohol. Both of these neigher undergo aldol condensation nor cannizzaro reaction.