Chemistry
Chemistry
10th Edition
ISBN: 9781305957404
Author: Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher: Cengage Learning
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**Question**: The following chemical transformations involve multistep mechanisms. Please write a reasonable mechanism for each transformation and label each elementary step.
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Transcribed Image Text:**Question**: The following chemical transformations involve multistep mechanisms. Please write a reasonable mechanism for each transformation and label each elementary step.
**Transcription of Reaction Mechanism**

**Chemical Reaction:**

Starting Material:
- 2-butanone (C<sub>4</sub>H<sub>8</sub>O)

Reagents:
- 1. Strong base "B"
- 2. Bromoethane (C<sub>2</sub>H<sub>5</sub>Br)

Product:
- 4-heptanone (C<sub>7</sub>H<sub>14</sub>O)

Byproducts:
- HB
- Br<sup>-</sup>

**Mechanism Explanation:**

1. **Deprotonation Step:**
   - The strong base "B" abstracts a hydrogen ion from the methyl group at position 2 of butanone, generating an enolate ion.

2. **Alkylation Step:**
   - The enolate ion acts as a nucleophile and attacks the electrophilic carbon in bromoethane, leading to the substitution and formation of a new C-C bond. This produces 4-heptanone as the main product while generating hydrogen bromide (HB) and bromide ion (Br<sup>-</sup>) as byproducts.

This reaction illustrates a typical alkylation of enolates using a strong base to form ketones from smaller ketones and alkyl halides.
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Transcribed Image Text:**Transcription of Reaction Mechanism** **Chemical Reaction:** Starting Material: - 2-butanone (C<sub>4</sub>H<sub>8</sub>O) Reagents: - 1. Strong base "B" - 2. Bromoethane (C<sub>2</sub>H<sub>5</sub>Br) Product: - 4-heptanone (C<sub>7</sub>H<sub>14</sub>O) Byproducts: - HB - Br<sup>-</sup> **Mechanism Explanation:** 1. **Deprotonation Step:** - The strong base "B" abstracts a hydrogen ion from the methyl group at position 2 of butanone, generating an enolate ion. 2. **Alkylation Step:** - The enolate ion acts as a nucleophile and attacks the electrophilic carbon in bromoethane, leading to the substitution and formation of a new C-C bond. This produces 4-heptanone as the main product while generating hydrogen bromide (HB) and bromide ion (Br<sup>-</sup>) as byproducts. This reaction illustrates a typical alkylation of enolates using a strong base to form ketones from smaller ketones and alkyl halides.
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