8. Provide a complete arrow-pushing mechanism for the following reaction. Be sure to illustrate the stereochemistry of any reactive intermediate(s) and the final product, if applicable. Br₂ CH₂Cl2

Organic Chemistry: A Guided Inquiry
2nd Edition
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Andrei Straumanis
Chapter14: Elimination
Section: Chapter Questions
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**Question 8: Mechanism and Stereochemistry**

Provide a **complete arrow-pushing mechanism** for the following reaction. Be sure to illustrate the stereochemistry of any reactive intermediate(s) and the final product, if applicable.

**Reaction:**
- A benzene ring depicted with a double bond is shown as the reactant.
- The reactant is treated with Br₂ in the presence of CH₂Cl₂.

**Explanation:**

In this reaction, it is implied that:

1. The benzene ring will undergo a bromination reaction with Br₂.
2. CH₂Cl₂ (dichloromethane) is used as the solvent.
3. The mechanism involves the formation of a bromonium ion intermediate, with subsequent attack by a bromide ion.
4. The stereochemistry of the reaction should be considered, particularly if any chiral centers are formed during the reaction.
5. The final product should be illustrated, showing the addition of bromine atoms and any key stereochemical features.

**Arrow-Pushing Guide:**

1. **Initiation Step:**
   - Show the formation of a bromonium ion.
   - Use curved arrows to illustrate the movement of electrons. Electrons from the π bond of the benzene attack Br₂, leading to the displacement of one bromine atom and forming a bromonium ion.

2. **Nucleophilic Attack:**
   - Illustrate how the bromide ion attacks the more substituted carbon atom, opening the bromonium ring.
   - Show the stereochemical outcome; often anti-addition occurs.

3. **Final Product:**
   - Depict the final product, clearly indicating the position and stereochemistry of the bromine atoms on the ring.

Note: The precise details of the stereochemical outcome will depend on the reaction conditions and the specific structure of the diketone substrate in question.
Transcribed Image Text:**Question 8: Mechanism and Stereochemistry** Provide a **complete arrow-pushing mechanism** for the following reaction. Be sure to illustrate the stereochemistry of any reactive intermediate(s) and the final product, if applicable. **Reaction:** - A benzene ring depicted with a double bond is shown as the reactant. - The reactant is treated with Br₂ in the presence of CH₂Cl₂. **Explanation:** In this reaction, it is implied that: 1. The benzene ring will undergo a bromination reaction with Br₂. 2. CH₂Cl₂ (dichloromethane) is used as the solvent. 3. The mechanism involves the formation of a bromonium ion intermediate, with subsequent attack by a bromide ion. 4. The stereochemistry of the reaction should be considered, particularly if any chiral centers are formed during the reaction. 5. The final product should be illustrated, showing the addition of bromine atoms and any key stereochemical features. **Arrow-Pushing Guide:** 1. **Initiation Step:** - Show the formation of a bromonium ion. - Use curved arrows to illustrate the movement of electrons. Electrons from the π bond of the benzene attack Br₂, leading to the displacement of one bromine atom and forming a bromonium ion. 2. **Nucleophilic Attack:** - Illustrate how the bromide ion attacks the more substituted carbon atom, opening the bromonium ring. - Show the stereochemical outcome; often anti-addition occurs. 3. **Final Product:** - Depict the final product, clearly indicating the position and stereochemistry of the bromine atoms on the ring. Note: The precise details of the stereochemical outcome will depend on the reaction conditions and the specific structure of the diketone substrate in question.
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