Acid-Catalyzed Nucleophilic Addition - Addition of Amines: Imine and Enamine Formation (mechanism!) 1° amines add to formimines (C=NR), and 2° amines yield enamines (R₂N-C=C) H30Ⓒ H* - H₂O - Alcohols Addition to yield hemiacetals (hemiketals), acetals (ketals) -C(OR')2 (mechanism!) H30Ⓒ + CHỊCH,NH, N-H CH₂CH₂OH (2 equiv.)

Organic Chemistry
9th Edition
ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
Chapter21: Carboxylic Acid Derivatives: Nucleophilic Acyl Substitution Reactions
Section21.SE: Something Extra
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Acid-Catalyzed Nucleophilic Addition
- Addition of Amines: Imine and Enamine Formation (mechanism!)
1° amines add to form imines (C=NR), and 2° amines yield enamines (R₂N-C=C)
CH,CH,NH2
H30*
+
H*
- H₂O
- Alcohols Addition to yield hemiacetals (hemiketals), acetals (ketals) -C(OR')2 (mechanism!)
H30Ⓡ
+
N-H
CH3CH₂OH
(2 equiv.)
Transcribed Image Text:Acid-Catalyzed Nucleophilic Addition - Addition of Amines: Imine and Enamine Formation (mechanism!) 1° amines add to form imines (C=NR), and 2° amines yield enamines (R₂N-C=C) CH,CH,NH2 H30* + H* - H₂O - Alcohols Addition to yield hemiacetals (hemiketals), acetals (ketals) -C(OR')2 (mechanism!) H30Ⓡ + N-H CH3CH₂OH (2 equiv.)
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