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CHM 102 Practice Questions Objective Question
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Question

Why do aldehydes undergo nucleophilic addition reactions while esters undergo nucleophilic acyl substitution reactions?
Options
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 Once the nucleophile adds to an aldehyde, neither H− nor R− can be eliminated since they are strongly basic.
Correct Answer
Correct Answer

Option D is the correct answer.

Detailed Explanation

In aldehydes, the tetrahedral intermediate has H and R groups attached, which are strongly basic and cannot be eliminated. In esters, the alkoxy group (OR) is a better leaving group and can be eliminated, leading to nucleophilic acyl substitution.

Hint

What groups are attached to the carbonyl carbon of aldehydes and esters?

Question Info

Course: CHM 102
Topic: Practice Questions
Type: Objective
Difficulty: Not specified
Question 1390 of 1999
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