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Summary
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Try to identify the enolate portion and the carbonyl portion in the different representations |
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STUDY TIPS:
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Related Reactions
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Step 1:
First, an acid-base reaction. The alkoxide functions as a base and removes the acidic a-hydrogen giving the reactive ester enolate. |
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Step 2: The nucleophilic ester enolate attacks the carbonyl C of another ester in a nucleophilic substitution process giving the tetrahedral intermediate. |
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Step 3: The intermediate collapses, reforming the C=O, resulting in loss of the leaving group, the alkoxide, leading to the b-ketoester product. |
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Note that the reaction is drawn to completion by deprotonation of the active methylene in the product by the ethoxide. The salt typically precipitates and is recovered after acid work-up. |
© Dr. Ian Hunt, Department of Chemistry |