Carboxylic Acid and Aldehyde-Ketone Silos

Carboxylic Acid and Aldehyde-Ketone Silos - DIBAL Aldehyde...

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Carboxylic Acid and Aldehyde/Ketone Silos OH O H O O Ketone Aldehyde Carboxylic Acid H 2 O/ H R(H) HO OH Hydrate ROH/H R(H) RO OR HCN R(H) HO CN Cyanohydrin Acetal RNH 2 /H N H R(H) N RNH 2 NaBH 3 CN Reductive Amination Enamine R(H) N R Imine R(H) NH R Amine K 2 Cr 2 O 7 1. NH 3 , HCN 2.H 2 O/H H 2 N OH O Strecker ! -amino acid With Aldehydes SOCl 2 or C 2 O 2 Cl 2 H 2 O Cl O Acid Cholride 1. Br 2. PPh 3 3. BuLi Wittig OH O O O O RSH SR O OR O ROH/ H Anhydride Thioester Ester N H O R Amide RNH 2 / H NH 2 O PCl 3 + * * Dehydration (-H 2 O) of an amide yields a nitrile OH O H 2 O N H 2 O/H or H 2 O/OH LAH NH 2 DIBAL H O R MgCl RCO 3 H Baeyer-Villiger Aldehyde Amine LAH NHR Amine R O Ketone P/Br 2 OH O Br NH 3 OH O H 2 N Hell ! -amino acid Ag NaOH Br 2 Br + CO 2 Hunsdiecker R OH O O " R O + CO 2 Special Case # -keto acid decarbonylation Carboxylic Acid Derivatives
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Unformatted text preview: DIBAL Aldehyde and Ketone Derivatives Reduction Oxidation HS SH S S H 1.BuLi 2. Br S S BF 3 HgCl 2 /HgO /H 2 O Dithio-acetal With Aldehydes AlCl 3 O Friedel-Crafts NH 2 NH 2 /OH or Hg/Zn/H 2 O Wolff-Kishner Clemmensen H MgCl-78C Fine print: These reactions should be viewed as general and specific exceptions will exist (as will additional arrows with addition reagents connecting the chemical species). A good faith effort was made to keep it as accurate as possible....
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This note was uploaded on 09/25/2009 for the course CH 223 taught by Professor Brown during the Spring '08 term at N.C. State.

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