Chapter 13 Carboxylic Acids, Esters, Amines, and Amides

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Acidity of Carboxylic AcidsCarboxylic acids• are weak acids.• ionize in water to produce carboxylate ionsand hydronium ions.Neutralization of Carboxylic AcidsCarboxylic acid salts• are a product of the neutralization of a carboxylic acid with a strong base.CH3—COOH + NaOH CH3—COO – Na + + H2Oacetic acidsodium acetate(carboxylic acid salt)• are used as preservatives and flavor enhancers.EstersIn an ester, the H in the carboxyl group is replacedwith an alkyl group.CH3 — C—O —CH3ester groupEsterification is the reaction of a carboxylic acid and alcohol in the presence of an acidcatalyst to produce an ester.O|| H +CH3—C—OH + H—O—CH2—CH3 _______________________>O||CH3—C—O—CH2—CH3 + H2Oethyl acetate (an ester)Ester ProductsAspirin• is used to relieve pain and reduce inflammation.• is an ester of salicylic acid and acetic acid.Oil of wintergreen• is used to soothe sore muscles.• is an ester of salicylic acid and methanol.Naming EstersThe name of an ester contains the names of• the alkyl group from the alcohol.• the carbon chain from the acid with –ate ending.methylethanoate (acetate)O||CH3— O—C —CH3IUPAC: methyl ethanoate
Esters in PlantsEsters give flowers and fruits their pleasant fragrances and flavors.Base hydrolysis or saponification,• is the reaction of an ester with a strong base.• produces the salt of the carboxylic acid and an alcohol.Cleaning Action of Soap• contains a nonpolar end that dissolves in nonpolar fats and oils, and a polar end thatdissolves in water.• forms groups of soap molecules called micelles that dissolve in water and are washedaway.Amines• are derivatives of ammonia, NH3.• contain N attached to one or more alkyl or aromatic groups.CH3⏐CH3⏐CH3—NH2 CH3—NH CH3—N—CH3Classification of AminesAmines are classified as primary, secondary, or tertiary.• In a primary (1°) amine, one carbon group is bonded to the nitrogen atom.• A secondary (2°) amine has two carbon groups bonded to the nitrogen atom.• A tertiary (3°) amine has three carbon groups bonded to the nitrogen atom.H CH3 CH3| | |CH3—N—H CH3—N—H CH3—N—CH31° 2° 3°Models of AminesThe three‐dimensional models show the shapes of amine molecules with one or morealkyl groups bonded to the nitrogen atom.Naming AminesSimple amines• are named as alkylamines.• List the names of the alkyl groups bonded to the N atom in alphabetical order in frontof amine.CH3—CH2—NH2 ethylamineCH3—NH—CH3 dimethylamineCH3|CH3—N—CH2—CH3ethyldimethylamine
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Page 5 and 6: Caffeine• is a stimulant of the c

Chapter 13 Carboxylic Acids, Esters, Amines, and Amides

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