CNGNGE JOHN MCMURRY CHAPTER 16 Carboxylic Acid Derivatives: Nucleophilic Acyl Substitution Reactions EDITION Organic Chemistry with Biological Applications
CHAPTER 16 Carboxylic Acid Derivatives: Nucleophilic Acyl Substitution Reactions
Carboxylic Acid Derivatives Carboxylic acid derivatives Compounds in which acyl group is bonded to an electronegative atom or substituent that can act as a leaving group Converted to parent carboxylic acid by hydrolysis reaction Carboxylic acid Acid halide Acid anhydride Ester (X=CI,Br) 0 R NH2 R -s8 0 (or OR') Amide Thioester Acyl phosphate
Carboxylic acid derivatives ▪ Compounds in which acyl group is bonded to an electronegative atom or substituent that can act as a leaving group ▪ Converted to parent carboxylic acid by hydrolysis reaction Carboxylic Acid Derivatives
Carboxylic Acid Derivatives Chemistry of all carboxylic derivatives is similar All undergo nucleophilic acyl substitution reaction + → Y
Chemistry of all carboxylic derivatives is similar ▪ All undergo nucleophilic acyl substitution reaction Carboxylic Acid Derivatives
16-1 Naming Carboxylic Acid Derivatives Acid Halides,RCOX Identify first the acyl group and then the halide Acyl group identified by replacing the-ic acid ending with-oyl or the -carboxylic acid ending with-carbonyl 0 H3C C-C Acetyl Benzoyl Cyclohexanecarbonyl chloride bromide chloride
Acid Halides, RCOX ▪ Identify first the acyl group and then the halide ▪ Acyl group identified by replacing the –ic acid ending with –oyl or the –carboxylic acid ending with –carbonyl 16-1 Naming Carboxylic Acid Derivatives
Naming Carboxylic Acid Derivatives Acid Anhydrides,RCO2COR' Symmetrical anhydrides of monocarboxylic acids and cyclic anhydrides of dicarboxylic acids named by replacing acid with anhydride H3C CH3 Acetic anhydride Benzoic anhydride Succinic anhydride
Acid Anhydrides, RCO2COR′ ▪ Symmetrical anhydrides of monocarboxylic acids and cyclic anhydrides of dicarboxylic acids named by replacing acid with anhydride Naming Carboxylic Acid Derivatives