Chemistry
Chemistry
10th Edition
ISBN: 9781305957404
Author: Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher: Cengage Learning
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Aldehydes and Ketones
Aldehydes and ketones are organic compounds that have a carbonyl group, C = O, as their functional group. They both differ in the placement of this carbonyl group in their structures.
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**Reaction Mechanism Explanation:** **Question:** 2. Provide a detailed mechanism for the following reaction: **Reaction Description:** - **Reactant:** The structure on the left is an alkylbenzene, specifically ethylbenzene, consisting of a benzene ring attached to an ethyl group (C₂H₅). - **Reagent:** NBS (N-Bromosuccinimide) is used as the brominating agent. - **Conditions:** The reaction takes place under the influence of light, indicating a radical bromination mechanism. - **Product:** The structure on the right shows bromination at the benzylic position, resulting in the formation of (1-bromoethyl)benzene. **Mechanism Overview:** 1. **Initiation:** - Light provides energy to homolytically cleave the bromine bond in NBS, generating bromine radicals. 2. **Propagation:** - A bromine radical abstracts a hydrogen atom from the benzylic (methyl) position of ethylbenzene, forming a benzylic radical. - The benzylic radical reacts with a bromine molecule (Br₂), formed from NBS, to form the brominated product and regenerate a bromine radical. 3. **Termination:** - Two bromine radicals may combine to form Br₂, or other possible radical combinations may terminate the reaction. This sequence illustrates the radical chain mechanism typical in NBS-mediated bromination, emphasizing the selectivity for the allylic or benzylic positions due to radical stability.
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Transcribed Image Text:**Reaction Mechanism Explanation:** **Question:** 2. Provide a detailed mechanism for the following reaction: **Reaction Description:** - **Reactant:** The structure on the left is an alkylbenzene, specifically ethylbenzene, consisting of a benzene ring attached to an ethyl group (C₂H₅). - **Reagent:** NBS (N-Bromosuccinimide) is used as the brominating agent. - **Conditions:** The reaction takes place under the influence of light, indicating a radical bromination mechanism. - **Product:** The structure on the right shows bromination at the benzylic position, resulting in the formation of (1-bromoethyl)benzene. **Mechanism Overview:** 1. **Initiation:** - Light provides energy to homolytically cleave the bromine bond in NBS, generating bromine radicals. 2. **Propagation:** - A bromine radical abstracts a hydrogen atom from the benzylic (methyl) position of ethylbenzene, forming a benzylic radical. - The benzylic radical reacts with a bromine molecule (Br₂), formed from NBS, to form the brominated product and regenerate a bromine radical. 3. **Termination:** - Two bromine radicals may combine to form Br₂, or other possible radical combinations may terminate the reaction. This sequence illustrates the radical chain mechanism typical in NBS-mediated bromination, emphasizing the selectivity for the allylic or benzylic positions due to radical stability.
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