Provide the mechanism for the following transformation. D =²H Br D DBr

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**Provide the mechanism for the following transformation. D = ²H**

The image illustrates a chemical reaction where an alkene is converted to a substituted cyclohexane compound through the addition of DBr (deuterium bromide).

**Description of the Reaction:**

1. **Starting Material:** 
   - The starting compound is a bicyclic compound with a double bond, specifically a 6-membered cyclohexene ring with a methyl group.

2. **Reagent:**
   - DBr, where D represents deuterium (²H), a stable isotope of hydrogen.

3. **Product:**
   - The product is a cyclohexane derivative where the double bond has been saturated.
   - The product includes a bromine (Br) atom and a deuterium (D) atom attached to the former double-bonded carbons.

**Explanation of Transformation:**

- **Mechanism Overview:**
  1. **Electrophilic Addition:** The double bond in the cyclohexene reacts with the electrophilic DBr. The π electrons attack the bromine in DBr, forming a carbocation intermediate.
  2. **Carbocation Stabilization:** The most stable carbocation forms, allowing for regioselective addition.
  3. **Nucleophilic Attack:** The bromide ion (Br⁻), from the breaking of the D-Br bond, attacks the carbocation from the opposite side, resulting in anti-addition.
  4. **Deuterium Addition:** Finally, deuterium (²H) is added to complete the formation of the saturated product with a new deuterium and bromine substituent.

This reaction is an example of an electrophilic addition mechanism, crucial in organic synthesis, showcasing regioselectivity and stereochemistry considerations.
Transcribed Image Text:**Provide the mechanism for the following transformation. D = ²H** The image illustrates a chemical reaction where an alkene is converted to a substituted cyclohexane compound through the addition of DBr (deuterium bromide). **Description of the Reaction:** 1. **Starting Material:** - The starting compound is a bicyclic compound with a double bond, specifically a 6-membered cyclohexene ring with a methyl group. 2. **Reagent:** - DBr, where D represents deuterium (²H), a stable isotope of hydrogen. 3. **Product:** - The product is a cyclohexane derivative where the double bond has been saturated. - The product includes a bromine (Br) atom and a deuterium (D) atom attached to the former double-bonded carbons. **Explanation of Transformation:** - **Mechanism Overview:** 1. **Electrophilic Addition:** The double bond in the cyclohexene reacts with the electrophilic DBr. The π electrons attack the bromine in DBr, forming a carbocation intermediate. 2. **Carbocation Stabilization:** The most stable carbocation forms, allowing for regioselective addition. 3. **Nucleophilic Attack:** The bromide ion (Br⁻), from the breaking of the D-Br bond, attacks the carbocation from the opposite side, resulting in anti-addition. 4. **Deuterium Addition:** Finally, deuterium (²H) is added to complete the formation of the saturated product with a new deuterium and bromine substituent. This reaction is an example of an electrophilic addition mechanism, crucial in organic synthesis, showcasing regioselectivity and stereochemistry considerations.
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