The behavior of esters and ketones in a reaction with a nucleophile is different because: 1) the carbonyl of the ketone is more positive. 2) the ester cannot form a tetrahedral intermediate. 3) the two oxygens of the ester sterically hinder the nucleophile attack. 4) there is a reasonable leaving group in the ester. O 3 O 2 O 4 O 1

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
Chapter24: Catalytic Carbon-carbon Bond Formation
Section: Chapter Questions
Problem 24.9P
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The behavior of esters and ketones in a reaction with a nucleophile is different because:
1) the carbonyl of the ketone is more positive.
2) the ester cannot form a tetrahedral intermediate.
3) the two oxygens of the ester sterically hinder the nucleophile attack.
4) there is a reasonable leaving group in the ester.
O 2
O 4
O 1
Transcribed Image Text:The behavior of esters and ketones in a reaction with a nucleophile is different because: 1) the carbonyl of the ketone is more positive. 2) the ester cannot form a tetrahedral intermediate. 3) the two oxygens of the ester sterically hinder the nucleophile attack. 4) there is a reasonable leaving group in the ester. O 2 O 4 O 1
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