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Br A Br B 1. AICI 3, 2. Zn(Hg), HCI 3. Br2, FeBr3 Br ? D Br E Br

Br A Br B 1. AICI 3, 2. Zn(Hg), HCI 3. Br2, FeBr3 Br ? D Br E Br

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 is the most likely product from the following sequence?
**Title: Synthesis of Bromo-Substituted Compounds through Electrophilic Aromatic Substitution and Side-Chain Reduction** **Description:** This diagram illustrates the multi-step synthesis of a bromo-substituted aromatic compound. The starting material is benzene, and the transformations involve an acylation reaction, reduction of the carbonyl group, and subsequent bromination. The final product needs to be identified among several possibilities. **Reagents and Conditions:** 1. **AlCl₃ (Friedel-Crafts Acylation Catalyst):** Utilized for the introduction of an acyl group to the benzene ring. 2. **Zn(Hg), HCl (Clemmensen Reduction):** Utilized for the reduction of the carbonyl group to a methylene group. 3. **Br₂, FeBr₃ (Bromination Catalysts):** Utilized for the electrophilic bromination of the aromatic ring. **Steps:** 1. **Friedel-Crafts Acylation:** - **Reaction:** Benzene is reacted with 2-chloropropanone (a compound with a ketone group) in the presence of aluminum chloride (AlCl₃) as a catalyst. - **Product:** The ketone group is introduced to the benzene ring, forming an acylated benzene. 2. **Clemmensen Reduction:** - **Reaction:** The acylated benzene is treated with zinc amalgam (Zn(Hg)) in the presence of hydrochloric acid (HCl). - **Product:** The carbonyl group (C=O) of the acylated benzene is reduced to a CH₂ group, resulting in an alkylbenzene (isopropylbenzene). 3. **Bromination:** - **Reaction:** The resulting alkylbenzene is treated with bromine (Br₂) in the presence of iron(III) bromide (FeBr₃) as a catalyst. - **Product:** A bromine atom is introduced to the benzene ring in the ortho, meta, or para position relative to the isopropyl group. **Identifying the Final Product:** Given the options A, B, C, D, and E: - Option A: 1-bromo-2-(1-methylethyl)benzene (ortho product) - Option B:
Transcribed Image Text:**Title: Synthesis of Bromo-Substituted Compounds through Electrophilic Aromatic Substitution and Side-Chain Reduction** **Description:** This diagram illustrates the multi-step synthesis of a bromo-substituted aromatic compound. The starting material is benzene, and the transformations involve an acylation reaction, reduction of the carbonyl group, and subsequent bromination. The final product needs to be identified among several possibilities. **Reagents and Conditions:** 1. **AlCl₃ (Friedel-Crafts Acylation Catalyst):** Utilized for the introduction of an acyl group to the benzene ring. 2. **Zn(Hg), HCl (Clemmensen Reduction):** Utilized for the reduction of the carbonyl group to a methylene group. 3. **Br₂, FeBr₃ (Bromination Catalysts):** Utilized for the electrophilic bromination of the aromatic ring. **Steps:** 1. **Friedel-Crafts Acylation:** - **Reaction:** Benzene is reacted with 2-chloropropanone (a compound with a ketone group) in the presence of aluminum chloride (AlCl₃) as a catalyst. - **Product:** The ketone group is introduced to the benzene ring, forming an acylated benzene. 2. **Clemmensen Reduction:** - **Reaction:** The acylated benzene is treated with zinc amalgam (Zn(Hg)) in the presence of hydrochloric acid (HCl). - **Product:** The carbonyl group (C=O) of the acylated benzene is reduced to a CH₂ group, resulting in an alkylbenzene (isopropylbenzene). 3. **Bromination:** - **Reaction:** The resulting alkylbenzene is treated with bromine (Br₂) in the presence of iron(III) bromide (FeBr₃) as a catalyst. - **Product:** A bromine atom is introduced to the benzene ring in the ortho, meta, or para position relative to the isopropyl group. **Identifying the Final Product:** Given the options A, B, C, D, and E: - Option A: 1-bromo-2-(1-methylethyl)benzene (ortho product) - Option B:
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