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Addition of HBr to the diene below forms four different products. Show the mechanism that accounts for the formation of all four products.

Addition of HBr to the diene below forms four different products. Show the mechanism that accounts for the formation of all four products.

Chemistry
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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**Title: Mechanism for the Addition of HBr to a Diene** **Description:** The image illustrates the chemical reaction where hydrogen bromide (HBr) is added to a cyclic diene, resulting in the formation of four different products. The diene structure consists of a six-membered ring with two double bonds, characteristic of a conjugated system. **Mechanism Explanation:** 1. **Initial Step: Protonation** - The reaction begins with the protonation of one of the double bonds in the diene by HBr. This step generates a carbocation and a bromide ion (Br⁻). 2. **Carbocation Formation and Resonance:** - The generated carbocation is stabilized through resonance. The positive charge can shift between the carbon atoms involved in the conjugated system, creating multiple resonance structures. 3. **Br⁻ Attack:** - The bromide ion can then attack at different positions of the carbocation. This results in different products depending on which carbon atom the bromide ion attaches to. 4. **Product Formation:** - The reaction yields four distinct products based on where exactly the Br⁻ ion adds across the conjugated double bond system. This illustrates the regioselectivity and stability provided by the resonance-stabilized carbocation intermediate. **Conclusion:** Understanding the mechanism of this reaction helps in comprehending how conjugated systems can produce various products due to their stability and the ability of intermediate structures to delocalize charge through resonance.
Transcribed Image Text:**Title: Mechanism for the Addition of HBr to a Diene** **Description:** The image illustrates the chemical reaction where hydrogen bromide (HBr) is added to a cyclic diene, resulting in the formation of four different products. The diene structure consists of a six-membered ring with two double bonds, characteristic of a conjugated system. **Mechanism Explanation:** 1. **Initial Step: Protonation** - The reaction begins with the protonation of one of the double bonds in the diene by HBr. This step generates a carbocation and a bromide ion (Br⁻). 2. **Carbocation Formation and Resonance:** - The generated carbocation is stabilized through resonance. The positive charge can shift between the carbon atoms involved in the conjugated system, creating multiple resonance structures. 3. **Br⁻ Attack:** - The bromide ion can then attack at different positions of the carbocation. This results in different products depending on which carbon atom the bromide ion attaches to. 4. **Product Formation:** - The reaction yields four distinct products based on where exactly the Br⁻ ion adds across the conjugated double bond system. This illustrates the regioselectivity and stability provided by the resonance-stabilized carbocation intermediate. **Conclusion:** Understanding the mechanism of this reaction helps in comprehending how conjugated systems can produce various products due to their stability and the ability of intermediate structures to delocalize charge through resonance.
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Step 1

Given : structure of reactant.

Tip :1-2 addition product and 1- 4 addition product will form.

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