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.)
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.)
Chemistry
10th Edition
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Chapter1: Chemical Foundations
Section: Chapter Questions
Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
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![**Acid-Catalyzed Nucleophilic Addition**
- **Addition of Amines: Imine and Enamine Formation (mechanism!)**
- **Primary Amines** add to form imines (\(C=NR\)), and **Secondary Amines** yield enamines (\(R_2N-C=C\)).
![Amines Reaction Diagram]
- **Diagram Explanation**:
- A cyclic ketone reacts with an ethylamine (\(CH_3CH_2NH_2\)) in the presence of hydronium ion (\(H_3O^+\)).
- The reaction produces an imine, where the oxygen of the ketone is replaced by the nitrogen of the amine group.
- **Alcohols Addition to yield Hemiacetals (hemiketals), Acetals (ketals) - (\(C(OR')_2\)) (mechanism!)**
![Alcohols Reaction Diagram]
- **Diagram Explanation**:
- A cyclic ketone reacts with ethanol (\(CH_3CH_2OH\), 2 equivalents) in the presence of hydronium ion (\(H_3O^+\)).
- The reaction leads to the formation of an acetal (or ketal) where the carbonyl oxygen is replaced by two alkoxy groups.
These two processes illustrate important mechanisms in organic chemistry for the transformation of carbonyl compounds into imines/enamines and acetals/ketals through acid-catalyzed nucleophilic addition.](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2Ffee5a196-0e10-4c2e-9c7f-7471e7c61611%2Fa427d7b8-b653-4bdf-a5f7-7ed9ad5ddd6b%2Fhxjo0hk_processed.jpeg&w=3840&q=75)
Transcribed Image Text:**Acid-Catalyzed Nucleophilic Addition**
- **Addition of Amines: Imine and Enamine Formation (mechanism!)**
- **Primary Amines** add to form imines (\(C=NR\)), and **Secondary Amines** yield enamines (\(R_2N-C=C\)).
![Amines Reaction Diagram]
- **Diagram Explanation**:
- A cyclic ketone reacts with an ethylamine (\(CH_3CH_2NH_2\)) in the presence of hydronium ion (\(H_3O^+\)).
- The reaction produces an imine, where the oxygen of the ketone is replaced by the nitrogen of the amine group.
- **Alcohols Addition to yield Hemiacetals (hemiketals), Acetals (ketals) - (\(C(OR')_2\)) (mechanism!)**
![Alcohols Reaction Diagram]
- **Diagram Explanation**:
- A cyclic ketone reacts with ethanol (\(CH_3CH_2OH\), 2 equivalents) in the presence of hydronium ion (\(H_3O^+\)).
- The reaction leads to the formation of an acetal (or ketal) where the carbonyl oxygen is replaced by two alkoxy groups.
These two processes illustrate important mechanisms in organic chemistry for the transformation of carbonyl compounds into imines/enamines and acetals/ketals through acid-catalyzed nucleophilic addition.
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Acid Catalysed Nucleophilic addition reactions of ketones.
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