Chap 15 16 practice answers %28synthesis%29 (1)

Chap 15 16 practice answers %28synthesis%29 (1) - 3 NO 2 Br...

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11. Multistep synthesis. Choose three of the following five compounds and show how you could prepare each one from benzene plus any other necessary reagents. (24 pts.) You may choose a fourth molecule to use a bonus (4 pts.) OH O Br Br O Br O O Br OH O SO 3 H OH 1 2 3 4 5 1 1. CH 3 Cl, AlCl 3 2. H 2 O CH 3 Na 2 Cr 2 O 7 , H + OH O Br 2 , FeBr 3 OH O Br Br 2 , FeBr 3 OH O Br Br OH O Br Br 2 O Br 1. CH 3 Cl, AlCl 3 2. H 2 O CH 3 Na 2 Cr 2 O 7 , H + OH O PBr 3 , Δ 3 HNO 3 , H 2 SO 4 NO 2 H 2 , Pd/C NH 2 NaNO 2 , H + 0 deg. C N N OH H + , H 2 O, Δ same as H 3 O + , Δ Br 2 , FeBr
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Unformatted text preview: 3 NO 2 Br Br Br Br O O Br Cl O 4 OH O 1. CH 3 Cl, AlCl 3 2. H 2 O CH 3 NBS, Br NaCN DMSO or acetone S N 2 solvents optional C N H 2 O, HCl, 5 SO 3 H OH 1. AlCl 3 , 2. H 2 O Cl H 2 SO 4 , SO 3 H major product is para product HNO 3 , H 2 SO 4 SO 3 H NO 2 H 2 , Pd/C SO 3 H NH 2 NaNO 2 , H + 0 deg. C SO 3 H N N H + , H 2 O, same as H 3 O + ,...
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Chap 15 16 practice answers %28synthesis%29 (1) - 3 NO 2 Br...

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