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4. Anhydride Mechanism. Draw the proper FULL electron-pushing mechanism for the reaction below, including ALL intermediates (with formal charges) and electron pushing arrows. Label the Electrophile and Nucleophile in each step! H2N но

4. Anhydride Mechanism. Draw the proper FULL electron-pushing mechanism for the reaction below, including ALL intermediates (with formal charges) and electron pushing arrows. Label the Electrophile and Nucleophile in each step! H2N но

Chemistry
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
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Draw the FULL electron-pushing mechanism for the reaction, including ALL intermediates (with formal charges) and electron pushing arrows. label the electrophile and nucleophile in each step!

**Anhydride Mechanism** Draw the proper FULL electron-pushing mechanism for the reaction below, including ALL intermediates (with formal charges) and electron-pushing arrows. Label the Electrophile and Nucleophile in each step. **Reaction:** - **Reactants:** - An acetic anhydride molecule, which includes two acyl groups (CH₃CO) bonded to a central oxygen. Each acyl group has a double-bonded oxygen with lone pairs. - An aniline molecule (C₆H₅NH₂), featuring a benzene ring attached to an amine group (NH₂) with a lone pair on the nitrogen. - **Products:** - An acetanilide molecule where the nitrogen of aniline forms an amide linkage with the carbonyl carbon of one acyl group from the acetic anhydride. - An acetic acid molecule left from the other acyl group in acetic anhydride bonding with an OH group. **Mechanism:** 1. **Step 1:** - Identify electrophile and nucleophile. - Aniline nitrogen attacks the carbonyl carbon of the acetic anhydride. 2. **Intermediates:** - Formation of a tetrahedral intermediate. - The carbonyl oxygen on acetic anhydride may carry a negative charge. 3. **Step 2:** - Reformation of the carbonyl group. - Formation of acetanilide and release of acetic acid.
Transcribed Image Text:**Anhydride Mechanism** Draw the proper FULL electron-pushing mechanism for the reaction below, including ALL intermediates (with formal charges) and electron-pushing arrows. Label the Electrophile and Nucleophile in each step. **Reaction:** - **Reactants:** - An acetic anhydride molecule, which includes two acyl groups (CH₃CO) bonded to a central oxygen. Each acyl group has a double-bonded oxygen with lone pairs. - An aniline molecule (C₆H₅NH₂), featuring a benzene ring attached to an amine group (NH₂) with a lone pair on the nitrogen. - **Products:** - An acetanilide molecule where the nitrogen of aniline forms an amide linkage with the carbonyl carbon of one acyl group from the acetic anhydride. - An acetic acid molecule left from the other acyl group in acetic anhydride bonding with an OH group. **Mechanism:** 1. **Step 1:** - Identify electrophile and nucleophile. - Aniline nitrogen attacks the carbonyl carbon of the acetic anhydride. 2. **Intermediates:** - Formation of a tetrahedral intermediate. - The carbonyl oxygen on acetic anhydride may carry a negative charge. 3. **Step 2:** - Reformation of the carbonyl group. - Formation of acetanilide and release of acetic acid.
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