Chapter 14: Organometallic Compounds |
Reactions of RLi and RMgX with Esters
Reaction type: Nucleophilic Acyl Substitution then Nucleophilic Addition
Summary:
REACTION OF
RLi or RMgX WITH AN ESTER |
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Step 1: The nucleophilic C in the organometallic reagent adds to the electrophilic C in the polar carbonyl group of the ester. Electrons from the C=O move to the electronegative O creating an intermediate metal alkoxide complex. |
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Step 2:
The tetrahedral intermediate collapses and displaces the alcohol portion of the ester as a leaving group, this produces a ketone as an intermediate. |
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Step 3:
The nucleophilic C in the organometallic reagent adds to the electrophilic C in the polar carbonyl group of the ketone. Electrons from the C=O move to the electronegative O creating an intermediate metal alkoxide complex. |
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Step 4:
This is the work-up step, a simple acid/base reaction. Protonation of the alkoxide oxygen creates the alcohol product from the intermediate complex.
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© Dr. Ian Hunt, Department of Chemistry |