Chapter_20_21_Lecture_08

Chapter_20_21_Lecture_08 - Organic Chemistry, 5th Edition...

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Chapter 20 and 21 Carboxylic Acids and Derivatives Adapted from:Jo Blackburn, Richland College, Dallas, TX Dallas County Community College District Organic Chemistry , 5 th Edition L. G. Wade, Jr. Acetic acid: vinegar and other foods, used industrially as solvent, catalyst, and reagent for synthesis. Fatty acids: fats and oils. Benzoic acid: in drugs and foods as a preservative. Adipic acid: used to make nylon 66. Phthalic acid: used to make polyesters.
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Chapter 20 2 Introduction The functional group of carboxylic acids consists of a C=O with -OH bonded to the same carbon. Aliphatic acids: R-COOH. Aromatic acids: Ph-COOH (aryl group). Fatty acids: long-chain aliphatic acids.
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Chapter 20 3 IUPAC Names Remove - e from alkane, add - oic acid . Number from the carbon of the carboxyl group. CH 3 CH 2 CHC Cl OH O 2-chlorobutanoic acid Ph C H C H COOH trans -3-phenylprop-2-enoic acid
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Chapter 20 4 Naming Cyclic Acids Cycloalkanes bonded to -COOH are named as cycloalkanecarboxylic acids. Aromatic acids are named as benzoic acids. COOH CH(CH 3 ) 2 2- isopropylcyclopentane carboxylic acid COOH OH o - hydroxybenzoic acid (salicylic acid) Naming cyclic acids will not be on the exam.
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Chapter 20 5 Dicarboxylic Acids For IUPAC name, number the chain from the end closest to a substituent. Two carboxyl groups on a benzene ring indicate a phthalic acid. HOOCCH 2 CHCH 2 CH 2 COOH Br 3-bromohexanedioic acid Pthalic acid O O O OH
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Chapter 20 6 Acid Derivatives All can be converted to the carboxylic acid by acidic or basic hydrolysis. Esters and amides common in nature. R C O X R C O O C O R' R C O O R R C O NH 2 R C N RCOX (RCO) 2 O RCOOR RCONH 2 RCN Acid Chloride Anhydride Ester Amide Nitrile
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Chapter 20 7 Naming Esters Esters are named as alkyl carboxylates. Alkyl from the alcohol, carboxylate from the carboxylic acid precursor. 2-methylpropyl ethanoate CH 3 CHCH 2 OCCH 3 CH 3 O C H 3 O O C H 3 O H methyl 4-hydroxy-3- methyl butan oate alcohol carboxylate
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Chapter 20 8 Cyclic Esters- Lactones For IUPAC name, add word lactone to the IUPAC acid name For common name or replace the - ic acid of common name with - olactone . O O H 3 C CH 3 4-hydroxy-2-methylpentanoic acid lactone Naming lactones will not be on the exam.
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Chapter 20 9 Naming Amides For 1 ° amide, drop - ic or - oic acid from the carboxylic acid name, add - amide . For 2
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Chapter_20_21_Lecture_08 - Organic Chemistry, 5th Edition...

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