10. Why do aldehydes undergo nucleophilic addition reactions (rxns from Unit 10) while esters undergo nucleophilic acyl substitution (rxns from Unit 11) 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.

Organic Chemistry
8th Edition
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Chapter6: Reactions Of Alkenes
Section: Chapter Questions
Problem 6.52P: As we have seen in this chapter, carbon-carbon double bonds are electron-rich regions that are...
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10. Why do aldehydes undergo nucleophilic addition reactions (rxns from Unit 10) while
esters undergo nucleophilic acyl substitution (rxns from Unit 11) 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.
Transcribed Image Text:10. Why do aldehydes undergo nucleophilic addition reactions (rxns from Unit 10) while esters undergo nucleophilic acyl substitution (rxns from Unit 11) 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.
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