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19. Aldehydes and Ketones:Nucleophilic Addition - Part 1 of 3

19. Aldehydes and Ketones:Nucleophilic Addition - Part 1 of 3

21. Aldehydes and Ketones: Nucleophilic Addition / DIBAL / Problem 6

Rationalize why the carbonyl oxygen of the ester attacks the aluminum of DIBAL-H instead of the alkoxy oxygen in the following reaction.

ANSWERS OPTIONS

A

The resonance hybrid of the ester shows that the carbonyl oxygen of the ester is more nucleophilic than the alkoxy oxygen.

B

The resonance hybrid of the ester shows that the alkoxy oxygen of the ester is more nucleophilic than the carbonyl oxygen.

C

The carbonyl oxygen is sterically less hindered hence it can more easily attack aluminum.

D

None of these.

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