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

a. (ii), (v), (vi), and (vii) contain `alpha`-H atom and hence undergo aldol condensation.
ii.
v.
vi.
vii.
b. (i), (iii), and (ix) do not contain `alpha`-H atom and hence undergo Cannizzaro reaction.
i. `2HCHO overset(Conc.)underset(NaOH)rarr HCOONa+CH_(3)OH`
iii. `PhCHO overset(Conc.)underset(NaOH)rarr PhCONa+PhCH_(2)OH`
ix.
c. The compound (iv) is a ketone and (viii) is an alcohol, so both undergo neither Aldol condensation nor Cannizzaro reaction.