20.12 Reaction of Organometallic Reagents with Carboxylic Acid Derivatives
- Page ID
- 28389
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Addition of Grignard reagents -- convert esters to 3o alcohols.
When reacting with esters, the Grignard reagent adds twice. The first addition forms a ketone, but Grignard reagents are strong enough nucleophiles to add to ketones as well. Therefore, the reaction continues to the tertiary alcohol.
General Reaction
Example 1: |
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Mechanism
1) Nucleophilic attack
2) Leaving group removal
3) Nucleophilic attack
4) Protonation
Organocuprate reagents convert acid chlorides to ketones
General Reaction
Example 1: |
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Contributors
Prof. Steven Farmer (Sonoma State University)
- Layne A. Morsch - University of Illinois Springfield