Which of the following compounds would undergo aldol condensation or the Cannizzaro reaction, or neither? Writer 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

I. 2-Methylpentanal (ii), cyclohexanone (v), 1-phenylpropanone (vI) and phenylacetaldehyde (vii) contain one or more `alpha`-hydrogens and hence undergo aldol condensation. The reactions and the structures of the expected products are given below:
.
II. Methanal (i), banzaldehyde (iii) and 2,2-dimethylbutanal (ix) do not contain `alpha`-hydrogen and hence undergo Cannizzaro reaction. the reactions and the structures of the expected products are given below:
.
III. Benzophenone (iv) is a ketone having no `alpha`-hydrogen/s while butan-1-ol (viii) is an alcohol. both of these neither undergo aldol condensation nor cannizzaro reaction.