Give a mechanism that accounts for the organic products of this reaction. Your mechanism must include a transition state that accounts for the stereochemistry of the product and/or reactant. Redraw the reagents as needed. CI ОН NaOH, DMSO + NaCl
Give a mechanism that accounts for the organic products of this reaction. Your mechanism must include a transition state that accounts for the stereochemistry of the product and/or reactant. Redraw the reagents as needed. CI ОН NaOH, DMSO + NaCl
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
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Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
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
Transcribed Image Text:**Title: Understanding Stereochemistry in Organic Reaction Mechanisms**
**Question:**
Give a mechanism that accounts for the organic products of this reaction. Your mechanism must include a transition state that accounts for the stereochemistry of the product and/or reactant. Redraw the reagents as needed.
**Reaction Details:**
- **Reactant:** A molecule with a chlorine atom (Cl) attached to a chiral carbon center, depicted as a wedge indicating its stereochemical orientation.
- **Reagents:** Sodium hydroxide (NaOH) and dimethyl sulfoxide (DMSO).
- **Product:** A molecule where the chlorine is replaced by a hydroxyl group (OH), with an inverted stereochemical orientation, depicted with a dashed wedge.
- **Byproduct:** Sodium chloride (NaCl).
**Explanation:**
This reaction illustrates a nucleophilic substitution mechanism, specifically an \( S_N2 \) reaction.
1. **Leaving Group:** The chlorine atom, which is part of the organic substrate, serves as the leaving group.
2. **Nucleophile:** The hydroxide ion (OH⁻) acts as the nucleophile, attacking the carbon bonded to the chlorine.
3. **Mechanism Overview:**
- The OH⁻ approaches the chiral carbon from the side opposite to the chlorine.
- A transition state is formed, where the nucleophile and leaving group are both partially bonded to the carbon simultaneously.
- As the OH⁻ forms a bond with the carbon, the Cl⁻ departs, resulting in the inversion of configuration at the chiral center, changing the stereochemistry.
4. **Final Product:** The chlorine is replaced by an OH group, demonstrating the stereochemical inversion characteristic of \( S_N2 \) reactions, resulting in the depicted alcohol with inverted orientation.
Understanding this type of stereochemical change is crucial for predicting the outcomes of reactions involving chiral centers.
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