PhOCH,C -NH Organic Chemistry,6th Edition COOH L.G.Wade,Jr. acylated. inactive Chapter 21 Carboxylic Acid Derivatives Jo Blackburn Richland College,Dallas,TX Dallas County Community College District ©2006，Prentice Hall
Chapter 21 Carboxylic Acid Derivatives Jo Blackburn Richland College, Dallas, TX Dallas County Community College District © 2006, Prentice Hall Organic Chemistry, 6th Edition L. G. Wade, Jr
0 PhOCH,C- NH CH CH COOH Acid Derivatives acylated. mnactive enzyme All can be converted to the carboxylic acid by acidic or basic hydrolysis. Esters and amides common in nature. -0-R C一NH R一C=N acid halide anhydride ester amide nitrile Condensed structure:RCOX (RCO).O RCO,R' RCONH, RCN Copyright2005 Pearson Prentice Hall,Inc. Chapter 21 2
Chapter 21 2 Acid Derivatives • All can be converted to the carboxylic acid by acidic or basic hydrolysis. • Esters and amides common in nature. =>
PhOCH,C. Naming Esters COOH inactive enzyme Esters are named as alkyl carboxylates. Alky/from the alcohol,carboxylate from the carboxylic acid precursor. CH3CH2-OH+HO一 CHgCH2-O-C-CH3 H2O ethanol ethanoic acid ethyl ethanoate ethyl alcohol acetic acid ethyl acetate => Chapter 21 3
Chapter 21 3 Naming Esters • Esters are named as alkyl carboxylates. • Alkyl from the alcohol, carboxylate from the carboxylic acid precursor. CH3CH2 OH HO C O CH3 H + + CH3CH2 O C + H2O O CH3 ethanol ethyl alcohol ethanoic acid acetic acid ethyl ethanoate ethyl acetate =>
0 PhOCH C NH CH CH COOH Name These acylated. inactive enzyme CH3 0 9 CH:CHCH2OCCH3 HCOCH2 isobutyl acetate benzyl formate 2-methylpropyl ethanoate benzyl methanoate Chapter 21 4
Chapter 21 4 Name These CH3CHCH2OCCH3 CH3 O HCOCH2 O isobutyl acetate 2-methylpropyl ethanoate benzyl formate benzyl methanoate =>
PhOCH.C Cyclic Esters COOH inactive enzyme Reaction of-OH and-COOH on same molecule produces a cyclic ester,lactone. To name,add word lactone to the IUPAC acid name or replace the -ic acid of common name with -olactone. 4-hydroxy-2-methylpentanoic acid lactone a-methyl-y-valerolactone CH; 三> Chapter 21 5
Chapter 21 5 Cyclic Esters • Reaction of -OH and -COOH on same molecule produces a cyclic ester, lactone. • To name, add word lactone to the IUPAC acid name or replace the -ic acid of common name with -olactone. O O H3 C CH3 4-hydroxy-2-methylpentanoic acid lactone -methyl--valerolactone =>