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NBS, A peroxide

NBS, A peroxide

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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What are the major products (include stereoisomers) of the following reaction? The peroxide works as light, hν. So, read “NBS/hν.”

 

 

**Title: Radical Bromination using N-Bromosuccinimide (NBS)** **Overview:** The following image depicts a chemical reaction involving N-Bromosuccinimide (NBS) used for the radical bromination of an alkene. This transformation occurs under the conditions of heat (denoted by the delta symbol, ∆) and the presence of a peroxide initiator. **Diagram Explanation:** - **Starting Material:** The structure on the left side of the reaction arrow represents a hydrocarbon chain with a benzene ring. The molecule can be described as a phenyl group attached to a carbon chain that contains a terminal double bond (alkene). - **Reagents and Conditions:** The arrow pointing to the right indicates the reaction direction and the necessary reagents/conditions: - **NBS (N-Bromosuccinimide):** Commonly used for selective bromination. - **∆ (Heat):** Indicates that the reaction requires heating. - **Peroxide:** Acts as a radical initiator to start the bromination process. **Reaction Mechanism:** 1. **Initiation:** The peroxide decomposes under heat to form radicals. 2. **Propagation:** - The bromine radical (formed from NBS) abstracts a hydrogen atom from the allylic position (position adjacent to the double bond), forming an allylic radical. - The allylic radical reacts with molecular bromine (formed by NBS decomposition) to form the brominated product. 3. **Termination:** Bromine radicals recombine to terminate the reaction. **Key Points:** - The procedure is highly selective for allylic bromination (bromination at the carbon adjacent to the double bond). - The use of peroxide as a radical initiator is crucial for the generation of bromine radicals. - Heating (∆) is required to decompose the peroxide and generate the necessary radicals. This method is widely used in organic synthesis for modifying carbon frameworks and introducing bromine atoms in a controlled manner.
Transcribed Image Text:**Title: Radical Bromination using N-Bromosuccinimide (NBS)** **Overview:** The following image depicts a chemical reaction involving N-Bromosuccinimide (NBS) used for the radical bromination of an alkene. This transformation occurs under the conditions of heat (denoted by the delta symbol, ∆) and the presence of a peroxide initiator. **Diagram Explanation:** - **Starting Material:** The structure on the left side of the reaction arrow represents a hydrocarbon chain with a benzene ring. The molecule can be described as a phenyl group attached to a carbon chain that contains a terminal double bond (alkene). - **Reagents and Conditions:** The arrow pointing to the right indicates the reaction direction and the necessary reagents/conditions: - **NBS (N-Bromosuccinimide):** Commonly used for selective bromination. - **∆ (Heat):** Indicates that the reaction requires heating. - **Peroxide:** Acts as a radical initiator to start the bromination process. **Reaction Mechanism:** 1. **Initiation:** The peroxide decomposes under heat to form radicals. 2. **Propagation:** - The bromine radical (formed from NBS) abstracts a hydrogen atom from the allylic position (position adjacent to the double bond), forming an allylic radical. - The allylic radical reacts with molecular bromine (formed by NBS decomposition) to form the brominated product. 3. **Termination:** Bromine radicals recombine to terminate the reaction. **Key Points:** - The procedure is highly selective for allylic bromination (bromination at the carbon adjacent to the double bond). - The use of peroxide as a radical initiator is crucial for the generation of bromine radicals. - Heating (∆) is required to decompose the peroxide and generate the necessary radicals. This method is widely used in organic synthesis for modifying carbon frameworks and introducing bromine atoms in a controlled manner.
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