12- Nucleophilic addition-elimination
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12 Terms
What mechanism occurs when acyl chlorides react with nucleophiles?
Nucleophilic addition–elimination.
What are the two stages of the mechanism?
Nucleophilic addition followed by elimination.
What happens during nucleophilic addition?
The nucleophile attacks the δ⁺ carbonyl carbon and the C=O π electrons move onto the oxygen.
What happens during elimination?
The C=O bond reforms and the leaving group is eliminated.
What is the nucleophile when an acyl chloride reacts with an alcohol?
The alcohol oxygen, using a lone pair of electrons.
Where does the nucleophile attack?
The δ⁺ carbonyl carbon.
What happens to the C=O π bond electrons when the nucleophile attacks?
They move onto the oxygen atom.
What happens when the C=O bond reforms?
The leaving group is eliminated.
What must curly arrows show?
The movement of electron pairs.
What should a curly arrow from an alcohol oxygen show?
The lone pair on oxygen attacking the δ⁺ carbonyl carbon.
What should a curly arrow from the C=O bond show?
The C=O π electrons moving onto the oxygen.