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Question -

Which of the following compounds would undergo aldolcondensation, which the Cannizzaro reaction and which neither? Write thestructures of the expected products of aldol condensation and Cannizzaroreaction.



Answer -

(i) Methanal (ii) 2-Methylpentanal

(iii) Benzaldehyde (iv) Benzophenone

(v) Cyclohexanone (vi) 1-Phenylpropanone

(vii) Phenylacetaldehyde (viii) Butan-1-ol

(ix) 2, 2-Dimethylbutanal

Answer

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

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

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

Aldol condensation

(ii)

(v)

(vi)

(vii)

Cannizzaro reaction

(i)

(iii)

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