Synthesis of Hexyl Acetate via an Sn2 Reaction. DMF Br Heat

Chemistry
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ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
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write a detailed arrow pushing mechanism for the synthesis of n- Hexyl acetate reaction?

**Synthesis of Hexyl Acetate via an SN2 Reaction**

In the provided diagram, we are given a step-by-step depiction of the synthesis of hexyl acetate, a typical ester, through an SN2 (bimolecular nucleophilic substitution) reaction.

### Reactants:

1. **Acetate Ion (AcO^-)**:
   - Depicted as having a negative charge on the oxygen, connected to a methyl group.
   - The counterion is potassium (K^+).

2. **1-Bromohexane**:
   - The structure includes a six-carbon chain (hexyl) with a terminal bromine (Br) atom.

### Solvent and Conditions:

- **Dimethylformamide (DMF)** and **Heat**:
  - DMF is a polar aprotic solvent that supports SN2 reactions by dissolving the reactants and not interacting with them significantly.

### Reaction Pathway:

- The acetate ion acts as a nucleophile, attacking the electrophilic carbon atom that is bonded to the bromine in 1-bromohexane. 
- The bromine, being a good leaving group, departs with an electron pair.
- The result of this nucleophilic substitution is the formation of hexyl acetate, where the acetate group (CH3COO) is now bonded to the hexyl chain (C6H13).

### Product:

- **Hexyl Acetate**:
  - An ester with the formula CH3COOC6H13.
  - Exhibits characteristic ester properties such as a pleasant fruity smell.

This reaction exemplifies the SN2 mechanism, highlighting the role of a strong nucleophile and the displacement of a leaving group.
Transcribed Image Text:**Synthesis of Hexyl Acetate via an SN2 Reaction** In the provided diagram, we are given a step-by-step depiction of the synthesis of hexyl acetate, a typical ester, through an SN2 (bimolecular nucleophilic substitution) reaction. ### Reactants: 1. **Acetate Ion (AcO^-)**: - Depicted as having a negative charge on the oxygen, connected to a methyl group. - The counterion is potassium (K^+). 2. **1-Bromohexane**: - The structure includes a six-carbon chain (hexyl) with a terminal bromine (Br) atom. ### Solvent and Conditions: - **Dimethylformamide (DMF)** and **Heat**: - DMF is a polar aprotic solvent that supports SN2 reactions by dissolving the reactants and not interacting with them significantly. ### Reaction Pathway: - The acetate ion acts as a nucleophile, attacking the electrophilic carbon atom that is bonded to the bromine in 1-bromohexane. - The bromine, being a good leaving group, departs with an electron pair. - The result of this nucleophilic substitution is the formation of hexyl acetate, where the acetate group (CH3COO) is now bonded to the hexyl chain (C6H13). ### Product: - **Hexyl Acetate**: - An ester with the formula CH3COOC6H13. - Exhibits characteristic ester properties such as a pleasant fruity smell. This reaction exemplifies the SN2 mechanism, highlighting the role of a strong nucleophile and the displacement of a leaving group.
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