CHAPTER 17 Carboxylic Acids, Esters, & Amides General, Organic, & Biological Chemistry
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CHAPTER 17 Carboxylic Acids, Esters, & Amides General, Organic, & Biological Chemistry Janice Gorzynski Smith Smith, Janice Gorzynski. General, Organic, & Biological Chemistry 2nd Ed. 1 CHAPTER 17 Carboxylic Acids, Esters, & Amides Learning Objectives: Nomenclature for carboxylic acids, esters, & amides Identify and describe structure of carboxylic acids, esters & amides Acid-base chemistry of carboxylic acids (think soap!) Substitution reactions of carboxylic acids Formation of esters Formation of amides Hydrolysis of acyl compounds Ester hydrolysis Amide hydrolysis Structure & formation of polyamides & polyesters CH 17 Homework: End of Chapter problems: 38, 40, 42, 48, 50, 52, 56, 58, 62, 68, 70, 72, 74, 78, 79, 80, 81, 82, 86, 90, 92, 97, 105 Smith, Janice Gorzynski. General, Organic, & Biological Chemistry 2nd Ed. 2 Examples Carboxylic Acids, Esters, Amides Reactivity Carboxylic Acids, Ester, Amides Structure Carboxylic Acids Smith, Janice Gorzynski. General, Organic, & Biological Chemistry 2nd Ed. 5 Carboxylic Acids Nomenclature O 4 5 2 3 1 OH prefix + parent + Suffix ane ene yne ol halide thiol (SH) aldehyde ketone Prefix alkyl alkenyl alkynyl hydroxy alkoxy fluoro, chloro, bromo, iodo mercapto formyl oxo amide carbamoyl amide suffix prefix First give location and type of substituents. parent How many carbons in longest chain? Carboxylic acid @ C1 suffix What is the functional group? How many? Carboxylic acid: “-oic acid” 2,4-dimethyl Functional Group alkane alkene alkyne alcohol (OH) ether petan oic acid thiol al one oic acid carboxylic carboxylic acid carboxy acid ester oxycarbonyl oate * Note: when we have more then 1 functional group the parent name has an “a” added on: hexa instead of hex Smith. General Organic & Biolocial Chemistry 2nd Ed. 6 Intermolecular Forces Carboxylic Acids Reactivity Carboxylic Acids Reactivity Carboxylic Acids Reactivity Carboxylic Acids Structure Esters Smith, Janice Gorzynski. General, Organic, & Biological Chemistry 2nd Ed. 11 Esters Nomenclature Functional Group alkane alkene alkyne alcohol (OH) ether O 3 4 prefix + 1 2 parent + O Suffix ane ene yne ol halide thiol (SH) aldehyde ketone Prefix alkyl alkenyl alkynyl hydroxy alkoxy fluoro, chloro, bromo, iodo mercapto formyl oxo amide carbamoyl amide suffix prefix First give location and type of substituents. Then give the name of the alky group bonded to the ester functional group parent How many carbons in longest chain? Carbonyl carbon @ C1 suffix What is the functional group? How many? Ester: “-oate” methyl butan oate thiol al one oic acid carboxylic carboxylic acid carboxy acid ester oxycarbonyl oate * Note: when we have more then 1 functional group the parent name has an “a” added on: hexa instead of hex 12 Smith. General Organic & Biolocial Chemistry 2nd Ed. Structure Amides Smith, Janice Gorzynski. General, Organic, & Biological Chemistry 2nd Ed. 13 Amide Nomenclature O 3 4 1 2 N H H prefix + prefix parent + Suffix ane ene yne ol halide thiol (SH) aldehyde ketone Prefix alkyl alkenyl alkynyl hydroxy alkoxy fluoro, chloro, bromo, iodo mercapto formyl oxo amide carbamoyl amide suffix First give location and type of substituents. parent How many carbons in longest chain? Carbonyl carbon @ C1 suffix What is the functional group? How many? Amide: “-amide” 3-methyl butan Functional Group alkane alkene alkyne alcohol (OH) ether amide thiol al one oic acid carboxylic carboxylic acid carboxy acid ester oxycarbonyl oate * Note: when we have more then 1 functional group the parent name has an “a” added on: hexa instead of hex 14 Smith. General Organic & Biolocial Chemistry 2nd Ed. Amide Nomenclature Functional Group alkane alkene alkyne alcohol (OH) ether O 3 4 1 2 prefix + prefix parent + N parent How many carbons in longest chain? Carbonyl carbon @ C1 suffix What is the functional group? How many? Amide: “-amide” butan amide carbamoyl amide suffix Use “N” to indicate naming amide R groups NN-dimethyl Suffix ane ene yne ol halide thiol (SH) aldehyde ketone Prefix alkyl alkenyl alkynyl hydroxy alkoxy fluoro, chloro, bromo, iodo mercapto formyl oxo amide thiol al one oic acid carboxylic carboxylic acid carboxy acid ester oxycarbonyl oate * Note: when we have more then 1 functional group the parent name has an “a” added on: hexa instead of hex 15 Smith. General Organic & Biolocial Chemistry 2nd Ed. Structure Amides Reactivity Substitution Reactivity Substitution Reactivity Substitution Reactivity Substitution Reactivity Substitution Reactivity Hydrolysis Reactivity Hydrolysis Reactivity Hydrolysis Reactivity Polyamides Reactivity Polyamides Reactivity Polyesters Reactivity Polyesters
