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

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**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.
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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