CH_20_Review - Chem 118C Workshop Doug Kent Jim Hollister...

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Chem. 118C Workshop Doug Kent & Jim Hollister LSC Ch.20 Review Sheet (Vollhardt & Schore, 5E) 1. TABLE: Reactions Of Carboxylic Acids and Carboxylic Acid Derivatives (CAD's) CAD Hydrolysis (add H 2 O) Alcoholysis (add R'OH) Ammonolysis (add NH 3 )/Amino- lysis (add R'NH 2 or R' 2 NH) Alkylation (add R' - from R'Li, R'MgX or R' 2 CuLi) 1 Hydride Reduction (add H - from LiAlH 4 ) 1 Acid Halide (RCOX) (X=Cl or Br) RCO 2 H (carb. acid) 11 + HX (g) 2 RCO 2 R' (ester) + HX (g) 2 RCONH 2 , RCONHR', or RCONR' 2 (amides) 3 1. with 2 mols R'Li or R'MgX: get RC(OH)R' 2 2. with R' 2 CuLi: RCOR' (ketone) RCH 2 OH (1 o alcohol) 4 Acid Anhydride (RCO) 2 O 2 RCO 2 H (carb. acid) RCO 2 R' (ester) + RCO 2 H (carb. acid) RCONH 2 , RCONHR', or RCONR ' 2 (amides) 3 Dr. Nasiri covers though not it text. ********** Dr. Nasiri covers? ********** Carboxylic Acid (Ch.19 Rxns) (RCO 2 H) ********** RCO 2 R' + H 2 O 12 RCONH 2 , RCONHR' or RCONR' 2 (amides) 5 (+ H 2 O) ********** RCH 2 OH (1 o alcohol) Ester (RCO 2 R'') RCO 2 H (carb. acid) + R"OH 6 RCO 2 R' (ester) + R"OH (transesterifica- tion) 13 RCONH 2 , RCONHR', or RCONR' 2 (amides) + R"OH (no catalyst necessary but need heat) RC(OH)R' 2 (3 o
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