Problem Set 3-solutions

Problem Set 3-solutions - Chem 3580 Spring 2009 Problem...

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Chem 3580 - Spring 2009 Problem Set #3 - Solutions There is more than one way of doing the synthesis. I encourage you to try alternative methods and perform critical assessment of each one. 1. (a) Retrosynthesis. Here it is possible to perform the dichlorination in one step because the sulfonate group will direct both into the meta positions. However, this approach will not work if the halogens were different. See an example below. You may also make the m-dichlorobenzene using combination of chlorination, nitration and Sandmeyer reaction. Cl Cl SO 3 H Cl Cl Cl Cl SO 3 H SO 3 H Forward synthesis Cl 2 (2 equiv) SO 3 SO 3 H Cl Cl SO 3 H Cl Cl Cl Cl SO 3 H SO 3 H 2 SO 4 FeCl 3 H 3 O + ! H 2 SO 4 Example for 2-bromo-4-chlorobenzenesulfonic acid NO 2 Cl NO 2 Cl NH 2 Cl N 2 Cl Br Cl Br SO 3 H HNO 3 H 2 SO 4 FeCl 3 H 2 Pd/C NaNO 2 , HCl O°C CuBr H 2 SO 4 Cl Cl 2 SO 3 (b) Retrosynthesis CH 3 NO 2 Br CH 3 NO 2 CH 3 Excess Forward synthesis AlCl 3 CH 3 Br Excess CH 3 CH 3 NO 2 CH 3 NO 2 Br HNO 3 H 2 SO 4 Br 2 , FeBr 3 !
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(c) Retrosynthesis NO 2 HOOC COOH
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Problem Set 3-solutions - Chem 3580 Spring 2009 Problem...

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