12.7 Which of the following compounds would undergo aldol condensation, which is the 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

Step 1: 
 

Aldehydes and ketones having at least one α-hydrogen undergo aldol condensation. The compounds (ii) 2−methylpentanal, (v) cyclohexanone, (vi) 1-phenylpropanone, and (vii) phenylacetaldehyde contain one or more α-hydrogen atoms. Therefore, these undergo aldol condensation.

Aldehydes having no α-hydrogen atoms undergo Cannizzaro reactions. The compounds (i) Methanal, (iii) Benzaldehyde, and (ix) 2, 2-dimethylbutanal do not have any α-hydrogen. Therefore, these undergo Cannizzaro reactions.

Compound (iv) Benzophenone is a ketone having no α-hydrogen atom and compound (viii) Butan-1-ol is an alcohol. Hence, these compounds do not undergo either aldol condensation or Cannizzaro reactions.

Step 2:

The aldol condensation products are as follows:
a. 2−Methylpentanal


b. Cyclohexanone,

c.
1-Phenylpropanone

d.
Phenyl acetaldehyde



Step 3:

The compound that gives the Cannizzaro reaction is as follows:

Cannizzaro reaction

a. 
Methanal

b.
Benzaldehyde

c.
2, 2-dimethylbutanal

Step 4:

The structure does not show either aldol condensation or cannizarro reaction are as follows:

Butan-1-ol and Benzophenone. 

The structures are as follows: