Organic Chemistry
8th Edition
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Chapter8: Haloalkanes, Halogenation, And Radical Reactions
Section: Chapter Questions
Problem 8.28P
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Question
Part B.)
What is the best description of the product(s) that form?
single enantiomer, achiral product, pair of enantiomers OR pair of diastereomers

Transcribed Image Text:**Title: Understanding the S<sub>N</sub>2 Reaction Mechanism**
**Introduction:**
This section will guide you through drawing the reaction product for a typical S<sub>N</sub>2 reaction. S<sub>N</sub>2 reactions are a type of nucleophilic substitution where the nucleophile attacks an electrophilic center, leading to the displacement of a leaving group.
**Reaction Details:**
- **Reactant:**
- Structure: A primary alkyl chloride
- Formula: CH<sub>3</sub>CH<sub>2</sub>CH<sub>2</sub>CH<sub>2</sub>Cl
- **Reagent:**
- Sodium hydroxide (NaOH)
**Mechanism:**
The image depicts an S<sub>N</sub>2 mechanism, characterized by its single-step process where the nucleophile, OH<sup>-</sup> (from NaOH), attacks the carbon that is bonded to the chlorine atom. Simultaneously, the chlorine atom leaves, resulting in an inversion of configuration at that carbon center.
**Expected Product:**
- The chlorine (Cl) atom is replaced by a hydroxyl group (OH), resulting in the formation of butanol.
- Structure of Product: CH<sub>3</sub>CH<sub>2</sub>CH<sub>2</sub>CH<sub>2</sub>OH
**Conclusion:**
This reaction exemplifies the classic S<sub>N</sub>2 mechanism where a nucleophile replaces a leaving group in a concerted, one-step process. The product is an alcohol derived from the original alkyl halide. Understanding these reactions is crucial in organic synthesis for forming new carbon-oxygen bonds.
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