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07 - Chem 212 Aldehyde and ketone problems 2 ANSWERS H OH H...

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H H OH H H O O O O H HO O Br O O O O O Cl H Cl Cl O O O HO OH O O H Br Br O O O NH 2 O O O OH O NHNH 2 NO 2 O 2 N O H N CHO CH 2 OH OH H OH H O H Br Br O O HO OH HS SH H H O N N O O OH O OMe OH HO O O racemic racemic Cl H Cl Cl HO OH H + catalyst diastereomers O OH CrO 3 , H 2 SO 4 CH 3 CH 2 CH 2 NH 2 pH = 4.5 H 2 , Pd/C OH S S MeOH H + 1) PPh 3 2) nBuLi 3) acetone NH 2 NH 2 , KOH NaBH 4 EtOH H + , H 2 O H + , H 2 O OH Br Br O H + , H 2 O H H 1) LiAlH 4 2) H + , H 2 O 1) EtMgBr 2) H 3 O + HN 1) pH 4.5 2) NaBH 4 , MeOH NOH NH 2 OH, H + O HCN, cat. NaOH N CrO 3 , pyridine Me 2 NH, H 2 O pH 4.5 benzaldehyde pH 4.5 H N NO 2 O 2 N + N OH , ZnCl 2 CrO 3 H 2 SO 4 H H OH pH 4.5 O O H + Ph 3 PCH 2 Ph KOH 1) Ph 3 P 2) nBuLi 3) propenal 1) Mg, ether
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