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
Section: Chapter Questions
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:**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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