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Esters Reaction with Amines The Aminolysis Mechanism Ester Reactions Summary and Practice Problems Preparation of Acyl (Acid) Chlorides (ROCl) Reactions of Acid Chlorides (ROCl) with Nucleophiles R 2 CuLi Organocuprates Gilman Reagent Reaction of Acyl Chlorides with Grignard and Gilman (Organocuprate) Reagents Reduction of Acyl Chlorides by LiAlH 4 , NaBH4, and LiAl(OtBu) 3 H Preparation and Reaction Mechanism of Carboxylic Anhydrides Amides Structure and Reactivity Naming Amides Amide Dehydration Mechanism by SOCl 2 , POCl 3 , and P 2 O 5 Amide Reduction Mechanism by LiAlH 4 Reduction of Amides to Amines and Aldehydes Amides Preparation and Reactions Summary Amides from Carboxylic Acids-DCC and EDC Coupling The Mechanism of Nitrile Hydrolysis To Carboxylic Acid Nitrile Reduction Mechanism with LiAlH4 and DIBAL to Amine or Aldehyde The Mechanism of Grignard and Organolithium Reactions with Nitriles The Reactions of Nitriles Converting Nitriles to Amides Carboxylic Acids to Ketones Esters to Ketones Carboxylic Acids and Their Derivatives Practice Problems Carboxylic Acids and Their Derivatives Quiz Reactions Map of Carboxylic Acid Derivatives