Mechanism For 1 & 2 Degree Amines - Lecture Notes | Lecture Note - Edubirdie

University:
York University
Course:
CHEM 2021 | Introductory Organic Chemistry II
Academic year:

2023
Views:

56

Pages:

1
Author:

Niklas

Mechanism for 1° Amines: Nucleophilic Attack: The lone pair on the nitrogen atom of the primary amine attacks the electrophilic carbon of the acylium ion, forming a new carbon-nitrogen bond. The benzene ring acts as a Lewis acid catalyst, stabilizing the intermediate. Proton Transfer (PT): A proton is transferred from the nitrogen atom to the oxygen atom of the intermediate, forming a carbocation intermediate. Loss of Water: A water molecule is eliminated from the carbocation intermediate, regenerating the aromatic ring and forming the final product, an amide. Mechanism for 2° Amines: Nucleophilic Attack: The lone pair on the nitrogen atom of the secondary amine attacks the electrophilic carbon of the acylium ion, forming a new carbon-nitrogen bond. Proton Transfer (PT): A proton is transferred from the nitrogen atom to a neighboring carbon atom, leading to the formation of a cyclic intermediate. Loss of Water: A water molecule is eliminated from the cyclic intermediate, resulting in the formation of the final product, an imine.

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