118C_Ch19_Review

118C_Ch19_Review - Chem. 118C Workshop Doug Kent/Jim...

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Chem. 118C Workshop Doug Kent/Jim Hollister LSC Major Reactions Of Carboxylic Acids (from Ch. 19, Vollhardt & Schore, 5th Ed) * Nucleophilic Substitution by Addition-Elimination PREPARATIONS OF CARBOXYLIC ACIDS OR THEIR DERIVATIVES Name Reaction Type Reagents, Solvents, Catalysts, etc. Products Comments 1. Oxidation of 1 o Alcohols or Aldehydes (ROH) Oxidation CrO 3 /H 2 SO 4 /H 2 O or KMnO 4 or HNO 3 Carboxylic Acid May use Na 2 Cr 2 O 7 or K 2 Cr 2 O 7 instead of CrO 3 2. Grignard Reagent + CO 2 Nucleophilic Addition to a Carbonyl Group 1) R ' MgX + CO 2 ; 2) H + /H 2 O Carboxylic Acid (Or can use alkyl lithium reagent, R ' Li); adds one C to R ' of Grignard or R ' Li Reagent (R ' =1 o , 2 o , 3 o , etc) 3. Nitrile Hydrolysis Hydrolysis 1) - OH/H 2 O/ ! 2) H + /H 2 O or H + /H 2 O/ ! Carboxylic Acid + NH 3 or NH 4 + make nitrile (1 o or 2 o ) via S N 2 rxn with NaCN + RX; adds one C to R group of RX. Partial hydolysis of nitrile
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This note was uploaded on 02/05/2012 for the course CHEM CHEM 118C taught by Professor Nambia during the Spring '09 term at UC Davis.

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