Ans Rev22 - 2 O heat H 2 O OH heat CH 3 CH 2 OH H 2 SO 4 O OH HO O O-HO O OCH 3 HO O NHCH 3 HO OH HO OH HO OH O O-O NH COCl CO 2 Et NHCH 3 NH 3 O

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Review of Chapter 20/22 Reactions of Carboxylic Acid Derivatives O Cl H 2 O NaOH, H 2 O CH 3 OH NH 2 NaOAc (or AcO - ) 1. LiAlH 4 2. H 2 O 1. CH 3 MgCl 2. H 2 O 1. (CH 3 ) 2 CuLi O OO H 2 O CH 3 OH NH 2 1. LiAlH 4 2. H 2 O O O O and / or O O H + , H 2 O heat H 2 O, OH - heat CH 3 OH, H + H 3 CN H 2 1. LiAlH 4 2. H 2 O 1. CH 3 MgCl 2. H 2 O 2. H 2 O 1. LiAlH[OCMe 3 ] 3 or DIBAL-H 2. H 2 O 1. LiAlH[OCMe 3 ] 3 or DIBAL-H 2. H 2 O O OH O ONa O OCH 3 O N H O O OH OH O O CH 3 OH O 2 OCH 3 O HO O + HO H N O O HO OH reduction O OH O HO + O - O HO + OCH 3 O NHCH 3 O OH HO + OH saponification trans- esterification reduction CHO
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Which of the above rxns are Fischer esterification, saponification, trans-esterification, and reduction ? HN O H + , H 2 O heat H 2 O, OH - heat CH 3 OH, H + H 3 CN H 2 1. LiAlH 4 2. H 2 O 1. CH 3 MgCl 2. H 2 O O O H + , H 2 O heat H 2 O, OH - heat 1. LiAlH 4 2. H 2 O NH O and / or CO 2 H SOCl 2 CH 3 CH 2 OH, H 2 SO 4 CN H +
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Unformatted text preview: 2 O heat H 2 O, OH- heat CH 3 CH 2 OH, H 2 SO 4 O OH HO O O-HO O OCH 3 HO O NHCH 3 HO OH HO OH HO OH O O-O NH COCl CO 2 Et NHCH 3 NH 3 O OH NH 2 O O-Fischer esterification saponification trans-esterification reduction reduction CO 2 H CO 2-CO 2 Et 1 R 2 R OH 3 R 1 R 2 R O 1 R 2 R OH 2 R 1 R Cl O OH COOH COOH COOH How do you carry out the following: R 2 CuLi 3 R MgX 2 R MgX CrO 3 , H + 1. PBr 3 2. Mg 3. CO 2 1. PBr 3 2. Mg 3. O 4. CrO 3 or 1. PBr 3 2. the malonic ester synthesis in Ch. 23...
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This note was uploaded on 06/11/2010 for the course CEM CEM252 taught by Professor ? during the Summer '10 term at Michigan State University.

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Ans Rev22 - 2 O heat H 2 O OH heat CH 3 CH 2 OH H 2 SO 4 O OH HO O O-HO O OCH 3 HO O NHCH 3 HO OH HO OH HO OH O O-O NH COCl CO 2 Et NHCH 3 NH 3 O

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