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Chapter 13 Carboxylic Acids, Esters, Amines, and Amides

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Chapter 13 Carboxylic Acids, Esters, Amines, and Amides Chapter 13 Carboxylic Acids, Esters, Amines, and Amides 13.1 Carboxylic Acids Copyright © 2005 by Pearson Education, Inc. Publishing as Benjamin Cummings 1 Carboxylic Acids A carboxylic acid contains a carboxyl group, which • is a carbonyl group (C=O) attached to a hydroxyl group (—OH). • is found on carbon 1 in carboxylic acids. O CH3 — C—OH hydroxyl group or CH3COOH carbonyl group 2 Models of Carboxylic Acids The three-dimensional models show the geometry of atoms in carboxylic acid molecules. 3 IUPAC Names The IUPAC names of carboxylic acids: • Replace the -e in the alkane name with -oic acid. CH4 methane HCOOH methanoic acid CH —CH ethane CH —COOH ethanoic acid 3 3 3 • Number substituents from the carboxyl carbon 1. CH3 O | ║ CH3—CH—CH2—C—OH 4 3 2 1 3-methylbutanoic acid 4 Names and Sources of Some Carboxylic Acids 5 Common Carboxylic Acids Methanoic acid (formic acid) O ║ H─C─OH ethanoic acid (acetic acid) O ║ CH3─C─OH 6 Aromatic Carboxylic Acids O Benzoic acid • is the aromatic C OH carboxylic acid. benzoic acid O O • locates substituents C OH C OH by numbering the ring from carbon 1 in the carboxyl group. Cl NH2 3-chlorobenzoic acid 4-aminobenzoic acid 7 Learning Check Give the IUPAC names of each compound. A. CH3─CH2─COOH propanoic acid CH3 | B. CH3─CH─CH2─COOH 3-methylbutanoic acid C. O C OH 3-bromobenzoic acid Br 8 Chapter 13 Carboxylic Acids, Esters, Amines and Amides 13.2 Properties of Carboxylic Acids Copyright © 2005 by Pearson Education, Inc. Publishing as Benjamin Cummings 9 Polarity of Carboxylic Acids Carboxylic acids • are strongly polar. • have two polar groups: hydroxyl (−OH) and carbonyl (C=O). 10 Polarity of Carboxylic Acids Carboxylic acids • form dimers in which hydrogen bonds form between two carboxyl groups. O H—O || | CH3—C C—CH3 | || O—H O A dimer of acetic acid • have higher boiling points than alcohols, ketones, and aldehydes of similar mass. 11 Comparison of Boiling Points Compound Molar Mass Boiling Point O ║ CH3−CH2−C−H 58 49 C CH3−CH2−CH2−OH 60 97 C O ║ CH3−C−OH 60 118 C 12 Solubility in Water Carboxylic acids: Water molecules • form hydrogen bonds with many water molecules. • with 1-4 carbon atoms are very soluble in water. 13 Boiling Points and Solubility 14 Acidity of Carboxylic Acids Carboxylic acids • are weak acids. • ionize in water to produce carboxylate ions and hydronium ions. O O ║ ║ – + CH3−C−OH + H2O CH3−C−O + H3O 15 Neutralization of Carboxylic Acids Carboxylic acid salts • are a product of the neutralization of a carboxylic acid with a strong base. – + CH3—COOH + NaOH CH3—COO Na + H2O acetic acid sodium acetate (carboxylic acid salt) • are used as preservatives and flavor enhancers. 16 Learning Check Write the equation for the reaction of propanoic acid with: A. water – + CH3—CH2—COOH + H2O CH3—CH2—COO + H3O B. KOH – + CH3—CH2—COOH + KOH CH3—CH2—COO K + H2O 17 Chapter 13 Carboxylic Acids, Esters, Amines, and Amides 13.3 Esters Copyright © 2005 by Pearson Education, Inc. Publishing as Benjamin Cummings 18 Esters In an ester, the H in the carboxyl group is replaced with an alkyl group. O CH3 — C—O —CH3 ester group 19 Esterification Esterification is the reaction of a carboxylic acid and alcohol in the presence of an acid catalyst to produce an ester. O H+ CH3—C—OH + H—O—CH2—CH3 O CH3—C—O—CH2—CH3 + H2O ethyl acetate (an ester) 20 Learning Check Write the equation for the reaction of propanoic acid and methanol in the presence of an acid catalyst. O H+ CH3—CH2—C—OH + H—O—CH3 propanoic acid methanol O CH3—CH2—C—O—CH3 + H2O 21 Ester Products Aspirin • 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. 22 Naming Esters The name of an ester contains the names of • the alkyl group from the alcohol. • the carbon chain from the acid with –ate ending. methyl ethanoate (acetate) O CH3— O—C —CH3 IUPAC: methyl ethanoate common: methyl acetate 23 Esters in Plants Esters give flowers and fruits their pleasant fragrances and flavors. Copyright © 2005 by Pearson Education, Inc. Publishing as Benjamin Cummings 24 Learning Check Give the IUPAC and common names of the following compound, which is responsible for the flavor and odor of pears. from 1-propanol O CH3—C—O—CH2—CH2—CH3 Propyl ethanoate (IUPAC) Propyl acetate (common) 25 Learning Check Draw the structure of the following compounds. A. 3-bromobutanoic acid Br | CH3—CH—CH2—COOH B. ethyl propionoate O CH3—CH2 —C—O—CH2—CH3 26 Acid Hydrolysis of Esters In acid hydrolysis • an ester reacts with water to produce a carboxylic acid and an alcohol. • an acid catalyst is required. O H+ H—C—O—CH2—CH3 + H2O O H—C—OH + H—O—CH2—CH3 27 Base Hydrolysis (Saponification) Base hydrolysis or saponification, • is the reaction of an ester with a strong base. • produces the salt of the carboxylic acid and an alcohol. O || CH3—C—O—CH2—CH3 + NaOH O – + CH3—C—O Na + HO—CH2—CH3 salt of carboxylic acid alcohol 28 Base Hydrolysis of Fatty Acids Produces Soaps 29 Cleaning Action of Soap A soap • contains a nonpolar end that dissolves in nonpolar fats and oils, and a polar end that dissolves in water. • forms groups of soap molecules called micelles that dissolve in water and are washed away. 30 Learning Check Write the organic products when methyl acetate reacts with A. water and an acid catalyst. O CH3—C—OH + HO—CH3 B. KOH. O – + CH3—C—O K + HO—CH3 31 Chapter 13 Carboxylic Acids, Ester, Amines, and Amides 13.4 Amines 32 Amines Amines • are derivatives of ammonia, NH3. • contain N attached to one or more alkyl or aromatic groups. CH CH 3 3 N H 2 CH3—NH2 CH3—NH CH3—N—CH3 33 Classification of Amines Amines 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—CH3 1° 2° 3° 34 Models of Amines The three-dimensional models show the shapes of amine molecules with one or more alkyl groups bonded to the nitrogen atom. 35 Naming Amines Simple amines • are named as alkylamines. • List the names of the alkyl groups bonded to the N atom in alphabetical order in front of amine. CH3—CH2—NH2 ethylamine CH3—NH—CH3 dimethylamine CH3 | CH3—N—CH2—CH3 ethyldimethylamine 36 Learning Check Give the common name and classify as primary, secondary, or tertiary. A. CH3—CH2—CH2—NH2 propylamine, 1° CH3 | B. CH3—CH2—N—CH3 ethyldimethylamine, 3° 37 Aromatic Amines • The amine of benzene is named aniline. • Alkyl groups on the N use the prefix N- with alkyl name. aniline 3-chloroaniline N-methylaniline 38 Learning Check Give the common name of each compound. A. CH3—NH—CH2—CH3 ethylmethylamine CH3 | B. CH3—CH2—N—CH2—CH3 diethylmethylamine C. NH2 aniline 39 Hydrogen Bonding for Amines The N−H bond • provides hydrogen bonding in 1°and 2° amines, but not in 3° amines. • is not as polar as the O-H bonds in alcohols. 40 Solubility in Water Amines • with 1-5 carbon atoms are soluble in water. • form hydrogen bonds with the polar O-H bond in water. 41 Learning Check Consider the following compounds: 1) CH3—CH2—CH2—NH2 2) CH3—CH2—NH—CH3 3) CH3—CH2—CH2—CH3 A. Which compound has the highest boiling point? 1) CH3—CH2—CH2—NH2 B. Which compound is soluble in water? 1) CH3—CH2—CH2—NH2 2) CH3—CH2—NH—CH3 42 Amines React as Bases Like ammonia, amines are weak bases in water. + – NH3 + H2O NH4 + OH ammonium hydroxide + – CH3—NH2 + H2O CH3—NH3 + OH methylammonium hydroxide 43 Neutralization forms Amine Salts An amine salt • forms when an amine is neutralized by acid. • is named by replacing the amine part of the name with ammonium followed by the name of the negative ion. + – CH3—NH2 + HCl CH3—NH3 Cl methylamine methylammonium chloride 44 Properties of Amine Salts Amine salts are • solids at room temperature. • soluble in water and body fluids. • the form used for drugs. 45 Alkaloids Alkaloids are • physiologically active nitrogen-containing compounds. • obtained from plants. • used as anesthetics, antidepressants, and in stimulants such as caffeine. • often addictive. 46 Cocaine Cocaine is • sold illegally as the amine salt. • reacted with NaOH to produce the free amine form known as “crack.” 47 Caffeine Caffeine • is a stimulant of the central nervous system. • is found in coffee beans, tea, chocolate, and soft drinks. 48 Nicotine Nicotine • increases the adrenaline level in the blood. • causes addiction to tobacco. N C H 3 49 Morphine and Codeine Morphine and codeine are • alkaloids. • obtained from the oriental poppy plant. • used as painkillers. • modified to make heroin. 50 Learning Check Write the structural formula for A methylpropylamine CH3–CH2–CH2–NH–CH3 B. 2-chloroaniline NH 2 Cl 51 Chapter 13 Carboxylic Acids, Esters, Amines, and Amides 13.5 Amides Copyright © 2005 by Pearson Education, Inc. Publishing as Benjamin Cummings 52 Amides In amides, • an amino group(–NH2) replaces the –OH group of carboxylic acids.
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