Draw a mechanism for this reaction: NH2 H,C CH, H,C

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Question: Draw out the mechanism

 

**Objective**: Draw a mechanism for the reaction shown.

**Reaction**:
- **Reactants**: Aniline (C₆H₅NH₂) and acetic anhydride ((CH₃CO)₂O)
- **Product**: N-phenylacetamide (C₆H₅NHCOCH₃)

**Instructions**:
Draw all missing reactants and/or products in the appropriate boxes by placing atoms on the canvas and connecting them with bonds. Add charges where needed. Electron-flow arrows should start on the electron(s) of an atom or bond and should end on an atom, bond, or location where a new bond should be created.

**Hints**:
- Determine what molecule is available for deprotonation. 
- The strongest base will accept the proton in the deprotonation step.

**Mechanism Diagram**:

1. **Top Left Box**: 
   - Shows the initial step where the nitrogen atom of aniline attacks the carbonyl carbon of acetic anhydride.
   - Use of curved arrows to indicate electron flow from the lone pair on nitrogen to the carbonyl carbon.

2. **Top Right Box**:
   - Formation of a tetrahedral intermediate.
   - Display of charges; the oxygen in the carbonyl group of acetic anhydride is negatively charged while the nitrogen is positively charged.

3. **Bottom Left Box**:
   - Collapse of the tetrahedral intermediate to form N-phenylacetamide.
   - Loss of leaving group (acetate ion).

4. **Bottom Right Box**:
   - Final deprotonation step.
   - Electron flow indicated by arrows, showing stabilization of the product.

**Submission**:
- Incorrect; try again. You have 7 attempts remaining.

Ensure the strongest base is correctly identified to accept the proton in the deprotonation step for accurate mechanism representation.
Transcribed Image Text:**Objective**: Draw a mechanism for the reaction shown. **Reaction**: - **Reactants**: Aniline (C₆H₅NH₂) and acetic anhydride ((CH₃CO)₂O) - **Product**: N-phenylacetamide (C₆H₅NHCOCH₃) **Instructions**: Draw all missing reactants and/or products in the appropriate boxes by placing atoms on the canvas and connecting them with bonds. Add charges where needed. Electron-flow arrows should start on the electron(s) of an atom or bond and should end on an atom, bond, or location where a new bond should be created. **Hints**: - Determine what molecule is available for deprotonation. - The strongest base will accept the proton in the deprotonation step. **Mechanism Diagram**: 1. **Top Left Box**: - Shows the initial step where the nitrogen atom of aniline attacks the carbonyl carbon of acetic anhydride. - Use of curved arrows to indicate electron flow from the lone pair on nitrogen to the carbonyl carbon. 2. **Top Right Box**: - Formation of a tetrahedral intermediate. - Display of charges; the oxygen in the carbonyl group of acetic anhydride is negatively charged while the nitrogen is positively charged. 3. **Bottom Left Box**: - Collapse of the tetrahedral intermediate to form N-phenylacetamide. - Loss of leaving group (acetate ion). 4. **Bottom Right Box**: - Final deprotonation step. - Electron flow indicated by arrows, showing stabilization of the product. **Submission**: - Incorrect; try again. You have 7 attempts remaining. Ensure the strongest base is correctly identified to accept the proton in the deprotonation step for accurate mechanism representation.
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