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

Solution:

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 since at least one α-hydrogen is required in the aldehyde or ketone to be able to undergo aldol condensation.

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

Compound (iv) Benzophenone is a ketone not having an α-hydrogen atom and compound (viii) Butan-1-ol is an alcohol. These compounds do not undergo either aldol condensation or cannizzaro reactions.