Orgo 225 Lecture 13 21.12 Preparation and Reactions of Amides Preparation of amides  Amides can be prepared from any of the carboxylic acid derivatives  Most efficiently prepared from acid chlorides Reactions Acid Catalyzed Hydrolysis of Amides Amides can be hydrolyzed to give carboxylic acids Base catalyzed Hydrolysis of Amides Amides can also be hydrolyzed when heated in basic aqueous conditions (this process is very slow) Reduction of Amides When treated with LAH, amides are converted to amides  The carbonyl group is completely removed 21.13 Preparation and Reactions of Nitriles Preparation of nitriles via SN2 reaction Nitriles can be prepared by treating an alkyl halide with a cyanide ion Preparation of nitriles from amides  Nitriles can be prepared via dehydration of an amide Hydrolysis of nitriles Occurs in aqueous acid conditions Nitriles are hydrolyzed to amides then further hydrolyzed to carboxylic acids Reactions between nitriles and Grignard reagents A ketone is obtained when a nitrile is treated with a Grignard reagent Grignard attacks the nitrile – the resulting anion is treated with aqueous acid to give an imine then hydrolyzed to a ketone Reduction of nitriles Nitriles are reduced to amines when treated with LAH 21.14 Synthesis Strategies C-C bond forming reactions c-c bond forming reactions in which the F.G remain