Friday Session-2-solution - Chem 3580 Spring 2010 Friday...

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Chem 3580 Spring 2010 Friday Session 2 – Solutions 1. Retrosynthesis NH 2 CN Br Br O Gilman Friedel-Crafts Acylation Reduction Free radical bromination S N 2 Reduction Proposed forward synthesis Br Peroxide Br CN NH 2 Br 2 FeCl 3 NBS NaCN H 2 Pt 1. CuLi 2 2. H 2 O Retrosynthesis + Friedel-Crafts Acylation Cl Cl O Reduction O Chlorination Cl O Proposed forward synthesis Cl O AlCl 3 , 2. H 2 O 1. O 1. Cl 2 , FeCl 3 2. H 3 O + Cl O H 2 , Pd/C Cl ———————————————————————————————————————————— Retrosynthesis H 2 N O 2 N O 2 N Br O 2 N Proposed forward synthesis: Note use of sec vinyl Gilman reagent. Last step is a selective reduction of NO 2 . HNO 3 H 2 SO 4 O 2 N Br 2 , FeBr 3 O 2 N Br CuI 2 O 2 N H 2 N (NH 4 ) 2 S
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Retrosynthesis CO 2 H NO 2 CO 2 H Forward synthesis CO 2 H CO 2 H NO 2 Cl FeCl 3 Excess 1. KMnO 4 HO 2. H 3 O + H 2 SO 4 HNO 3 Retrosynthesis: t-Butyl cation can come from any source. O
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Friday Session-2-solution - Chem 3580 Spring 2010 Friday...

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