Why do aldehydes undergo nucleophilic addition reactions while esters undergo nucleophilic acyl substitution reactions?
A)The carbonyl carbon of an ester is more electrophilic than that of an aldehyde.
B)Aldehydes are more sterically hindered than esters.
C)Once the nucleophile adds to an aldehyde,the tetrahedral intermediate is too sterically hindered to eliminate one of the attached groups.
D)The ester carbonyl carbon is sp3 hybridized while the aldehyde carbonyl carbon is sp2 hybridized.
E)Once the nucleophile adds to an aldehyde,neither H- nor R- can be eliminated since they are strongly basic.

Question

Quizplus · Accepted Answer

Once the nucleophile adds to an aldehyde, the resulting tetrahedral intermediate does not have a good leaving group, as both hydrogen (in the form of H-) and any alkyl group (R-) are strongly basic and thus poor leaving groups. This contrasts with esters, where the alkoxy group can act as a relatively good leaving group, facilitating nucleophilic acyl substitution.

Why Do Aldehydes Undergo Nucleophilic Addition Reactions While Esters Undergo