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Draw the major organic product for the reaction shown. Br2 (excess) FeBr3

Draw the major organic product for the reaction shown. Br2 (excess) FeBr3

Pushing Electrons
Pushing Electrons
4th Edition
ISBN:9781133951889
Author:Weeks, Daniel P.
Publisher:Weeks, Daniel P.
Chapter3: Mechanisms
Section: Chapter Questions
Problem 28EQ
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**Title:** Drawing the Major Organic Product for the Bromination Reaction **Description:** In the given reaction, we are tasked with drawing the major organic product. The starting material is acetophenone, which is a phenyl group (benzene ring) attached to a carbonyl group (C=O). The reagents specified are: - **Br₂ (excess):** Molecular bromine, used in excess. - **FeBr₃:** Iron(III) bromide, which acts as a catalyst. **Reaction Overview:** This setup indicates a bromination reaction of an aromatic compound. Typically, in such reactions, the aromatic ring undergoes electrophilic aromatic substitution. The presence of a carbonyl group (C=O) in acetophenone directs the bromination to the meta position relative to the carbonyl group. **Expected Product:** Based on the reaction conditions: - The major product will be a brominated acetophenone. - Bromine (Br) will substitute a hydrogen atom present at the meta position on the benzene ring due to the deactivating influence of the carbonyl group. By employing this reaction framework, we predict the product to be meta-bromoacetophenone. The excess of Br₂ ensures complete bromination at this preferred position. **Conclusion:** This exercise emphasizes understanding electrophilic aromatic substitution and the directing effects of substituents on a benzene ring. The FeBr₃ acts as a Lewis acid, enhancing the electrophilicity of Br₂, facilitating the reaction. This content forms part of an educational series on organic reaction mechanisms, providing foundational knowledge for chemistry students.
Transcribed Image Text:**Title:** Drawing the Major Organic Product for the Bromination Reaction **Description:** In the given reaction, we are tasked with drawing the major organic product. The starting material is acetophenone, which is a phenyl group (benzene ring) attached to a carbonyl group (C=O). The reagents specified are: - **Br₂ (excess):** Molecular bromine, used in excess. - **FeBr₃:** Iron(III) bromide, which acts as a catalyst. **Reaction Overview:** This setup indicates a bromination reaction of an aromatic compound. Typically, in such reactions, the aromatic ring undergoes electrophilic aromatic substitution. The presence of a carbonyl group (C=O) in acetophenone directs the bromination to the meta position relative to the carbonyl group. **Expected Product:** Based on the reaction conditions: - The major product will be a brominated acetophenone. - Bromine (Br) will substitute a hydrogen atom present at the meta position on the benzene ring due to the deactivating influence of the carbonyl group. By employing this reaction framework, we predict the product to be meta-bromoacetophenone. The excess of Br₂ ensures complete bromination at this preferred position. **Conclusion:** This exercise emphasizes understanding electrophilic aromatic substitution and the directing effects of substituents on a benzene ring. The FeBr₃ acts as a Lewis acid, enhancing the electrophilicity of Br₂, facilitating the reaction. This content forms part of an educational series on organic reaction mechanisms, providing foundational knowledge for chemistry students.
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