chm2211ps7sol - Organic Chemistry II Problem Set 7...

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C O Cl H 3 C NH 2 Br N O OC CH 3 CH 3 CH 3 CO OH N O O Organic Chemistry II Problem Set 7 Solutions Synthesis The answers are just one of several possible for each question. Show the steps you would use to synthesize the compounds below using toluene, benzene, any straight chain carboxylic acid, and alkyl halide with 4 or fewer carbons, and any common reagents you might need. Your solutions should show all structures. 1. a. chlorinate toluene using Cl 2 and FeCl 3 b. convert acetic acid to acetyl chloride using SOCl 2 c. use F.C. acylation reaction to add acetyl group to chlorobenzene (purify product to remove ortho) 2. a. make nitrobenzene from benzene using HNO 3 b. add Br at meta position using Br 2 and FeBr 3 c. reduce the –NO 2 to –NH 2 using Sn in HCl 3. a. add t-butyl group to benzene using F.C. alkylation b. add a nitro group using HNO 3 in H 2 SO 4 c. purify to remove ortho products (not much) 4. a. oxidize toluene to benzoic acid using MnO 4 1- b. add a nitro group using HNO 3 in H 2 SO 4
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CH CH CH 3
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chm2211ps7sol - Organic Chemistry II Problem Set 7...

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