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

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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What class of the reaction is the "synthesis of hexyI acetate reaction" an example of? What about the starting material suggest that it follows the reaction pathway?

**Synthesis of Hexyl Acetate via an Sn2 Reaction**

This image outlines the process for synthesizing hexyl acetate using an SN2 reaction mechanism. 

**Reactants:**
- On the left, there is a negatively charged acetate ion (OAc⁻), paired with a potassium ion (K⁺).
- A bromohexane molecule (Br–(CH₂)₅–CH₃) is shown next to the acetate ion.

**Reaction Conditions:**
- Dimethylformamide (DMF) is used as the solvent.
- The reaction requires heat to proceed.

**Product:**
- The product of this reaction is hexyl acetate, represented by the structure CH₃COO(CH₂)₅CH₃.

**Mechanism:**
In an SN2 reaction, the nucleophile, here the acetate ion, displaces the bromine atom in bromohexane through a backside attack, forming the ester hexyl acetate. This type of reaction is characterized by a single concerted step leading to inversion of configuration at the carbon center where the nucleophilic attack occurs.
Transcribed Image Text:**Synthesis of Hexyl Acetate via an Sn2 Reaction** This image outlines the process for synthesizing hexyl acetate using an SN2 reaction mechanism. **Reactants:** - On the left, there is a negatively charged acetate ion (OAc⁻), paired with a potassium ion (K⁺). - A bromohexane molecule (Br–(CH₂)₅–CH₃) is shown next to the acetate ion. **Reaction Conditions:** - Dimethylformamide (DMF) is used as the solvent. - The reaction requires heat to proceed. **Product:** - The product of this reaction is hexyl acetate, represented by the structure CH₃COO(CH₂)₅CH₃. **Mechanism:** In an SN2 reaction, the nucleophile, here the acetate ion, displaces the bromine atom in bromohexane through a backside attack, forming the ester hexyl acetate. This type of reaction is characterized by a single concerted step leading to inversion of configuration at the carbon center where the nucleophilic attack occurs.
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