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Show the product most likely to arise from the following reaction (3 minutes) Me Me Br Br Br Me Br2 Me FeBr3 Me A C

Show the product most likely to arise from the following reaction (3 minutes) Me Me Br Br Br Me Br2 Me FeBr3 Me A C

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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**Question:** Determine the product most likely to arise from the following reaction. Time allowed: 3 minutes. **Reaction:** Starting material: Acetophenone (a phenyl group attached to a carbonyl group, which is bonded to a methyl group) Reagents: Br₂, FeBr₃ **Possible Products:** - **A:** 4-Bromoacetophenone (with bromine at the para position to the carbonyl group) - **B:** 3-Bromoacetophenone (with bromine at the meta position to the carbonyl group) - **C:** 1-(3-Bromophenyl)propan-1-one (bromine at the meta position to the carbonyl, elongated carbon chain) - **D:** Acetophenone (no reaction) - **E:** Phenacyl bromide (bromine at the alpha position of the carbonyl) - **F:** Acetone Phenone (unaltered substrate structure) **Explanation:** This is an electrophilic aromatic substitution reaction. The presence of FeBr₃ suggests a Lewis acid-catalyzed bromination. The carbonyl group in acetophenone is a meta-directing group, which directs the bromine to the meta position relative to itself. Therefore, **option B** (3-Bromoacetophenone) is the most likely product. Be sure to verify your selection based on reaction conditions and directing effects of substituents during electrophilic aromatic substitution.
Transcribed Image Text:**Question:** Determine the product most likely to arise from the following reaction. Time allowed: 3 minutes. **Reaction:** Starting material: Acetophenone (a phenyl group attached to a carbonyl group, which is bonded to a methyl group) Reagents: Br₂, FeBr₃ **Possible Products:** - **A:** 4-Bromoacetophenone (with bromine at the para position to the carbonyl group) - **B:** 3-Bromoacetophenone (with bromine at the meta position to the carbonyl group) - **C:** 1-(3-Bromophenyl)propan-1-one (bromine at the meta position to the carbonyl, elongated carbon chain) - **D:** Acetophenone (no reaction) - **E:** Phenacyl bromide (bromine at the alpha position of the carbonyl) - **F:** Acetone Phenone (unaltered substrate structure) **Explanation:** This is an electrophilic aromatic substitution reaction. The presence of FeBr₃ suggests a Lewis acid-catalyzed bromination. The carbonyl group in acetophenone is a meta-directing group, which directs the bromine to the meta position relative to itself. Therefore, **option B** (3-Bromoacetophenone) is the most likely product. Be sure to verify your selection based on reaction conditions and directing effects of substituents during electrophilic aromatic substitution.
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