Chapter 14 Carboxylic Acids Esters Amines and Amides

Chapter 14 Carboxylic Acids, Esters, Amines, and Amides 1 14. 1 Carboxylic Acids Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc.

Carboxylic Acids 2 A carboxylic acid contains a carboxyl group, which consists of a hydroxyl group OH attached to the carbon in a carbonyl group. Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc.

IUPAC Names for Carboxylic Acids 3 In the IUPAC names of carboxylic acids, • the -e in the alkane name is replaced with -oic acid CH 4 CH 3—CH 3 • Methane Ethane HCOOH Methanoic acid CH 3—COOH Ethanoic acid substituents are numbered from the carboxyl carbon 1 CH 3 O CH 3—CH—CH 2—C—OH 4 3 2 1 3 -methylbutanoic acid Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc.

Common and IUPAC Names of Some Carboxylic Acids 4 Chemistry: An Introduction to General,

Common Carboxylic Acids 5 Methanoic acid (formic acid) O H C OH Ethanoic acid (acetic acid) O CH 3 C OH Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc.

Naming Carboxylic Acids 6 Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh

Naming Carboxylic Acids 7 Give the IUPAC name for the following carboxylic acid. Step 1 Identify the carbon chain containing the carboxyl group and replace the -e in the alkane name with -oic acid. Pentanoic acid Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc.

Naming Carboxylic Acids 8 Give the IUPAC name for the following carboxylic acid. Step 2 Give the location and name of each substituent on the main chain by counting the carboxyl carbon as 1. 2 -methylpentanoic acid Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc.

Aromatic Carboxylic Acids 9 Benzoic acid • is the simplest aromatic carboxylic acid • locates substituents by numbering the ring from carbon 1 in the carboxyl group Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc.

Alpha Hydroxy Acids (AHAs) 10 Alpha hydroxy acids (AHAs) are naturally occurring carboxylic acids with a hydroxyl group ( OH) on the carbon adjacent to the carboxyl group. Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc.

Alpha Hydroxy Acids (AHAs) 11 Alpha hydroxy acids (AHAs) • are used to remove acne scars and age spots • were used by Cleopatra, Queen of Egypt, who bathed in sour milk, which contains lactic acid, an AHA Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc.

Learning Check 12 Give the IUPAC names of each compound. A. CH 3 CH 2 COOH B. CH 3 | CH 3 CH CH 2 COOH C. Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc.

Solution 13 Give the IUPAC names of each compound. A. CH 3 CH 2 COOH propionoic acid B. CH 3 | CH 3 CH CH 2 COOH 3 -methylbutanoic acid C. 3 -bromobenzoic acid Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc.

Chapter 14 Carboxylic Acids, Esters, Amines, and Amides 14 14. 2 Properties of Carboxylic Acids Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc.

Polarity of Carboxylic Acids 15 Carboxylic acids are strongly polar because they have two polar groups hydroxyl ( OH) and carbonyl (C=O) Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc.

Solubility in Water 16 Carboxylic acids • form hydrogen bonds with many water molecules • with one to four carbon atoms are very soluble in water • as the number of carbons increases, the solubility of the carboxylic acid in water is reduced Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc.

Solubility in Water 17 Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh

Acidity of Carboxylic Acids 18 Carboxylic acids • are weak acids • ionize in water to produce carboxylate ions and hydronium ions • can lose a proton because two oxygen atoms in carboxylate ion stabilize negative charge O O CH 3 C OH + H 2 O CH 3 C O– + H 3 O+ carboxylic acid carboxylate ion Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc.

Learning Check 19 Write the balanced equation for the ionization of butanoic acid in water and identify the carboxylate ion. Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc.

Solution 20 Write the balanced equation for the ionization of butanoic acid in water and identify the carboxylate ion. O O CH 3 CH 2 C OH + H 2 O CH 3 CH 2 C O– + H 3 O+ carboxylic acid carboxylate ion Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc.

Neutralization of Carboxylic Acids 21 Carboxylic acid salts • are a product of the neutralization of a carboxylic acid with a strong base CH 3—COOH + Na. OH acetic acid • CH 3—COO– Na+ + H 2 O sodium acetate (carboxylic acid salt) are used as preservatives and flavor enhancers Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc.

Carboxylic Acid Salts 22 Carboxylic acid salts are used as preservatives and flavor enhancers such as • sodium propionate, which is used in cheese and breads • sodium benzoate, which inhibits growth of mold and bacteria and is added to fruit juices, margarine, relishes, salads, and jams • monosodium glutamate, MSG, which is added to meats, fish, vegetables, and baked goods to enhance flavor Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc.

Carboxylic Acid Salts 23 Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh

Carboxylic Acid Salts 24 Carboxylic acid salts • are ionic compounds with strong attractive forces between ions • are solids at room temperature • have high melting points • are usually soluble in water Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc.

Learning Check 25 Write the equation for the reaction of propanoic acid with A. water B. KOH Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc.

Solution 26 Write the equation for the reaction of propanoic acid with A. water CH 3—CH 2—COOH + H 2 O CH 3—CH 2—COO– + H 3 O+ B. KOH CH 3—CH 2—COOH + KOH CH 3—CH 2—COO– K+ + H 2 O Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc.

Chapter 14 Carboxylic Acids, Esters, Amines, and Amides 27 14. 3 Esters Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc.

Esters 28 Esters are • found in fats and oils • responsible for the aroma and flavor of bananas, oranges, and strawberries O CH 3 —C—O—CH 3 ester group Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc.

Esterification 29 Esterification is the reaction of a carboxylic acid and alcohol in the presence of an acid catalyst to produce an ester. The main chain of an ester comes from the carboxylic acid, while the alkyl group in an ester comes from the alcohol. Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc.

Esterification 30 An example of esterification is the reaction of a ethanoic acid with 1 -propanol to produce an ester called propylethanoate, responsible for the smell of pears. Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc.

Learning Check 31 Write the equation for the reaction of propanoic acid and methanol in the presence of an acid catalyst. Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc.

Solution 32 Write the equation for the reaction of propanoic acid and methanol in the presence of an acid catalyst. O CH 3—CH 2—C—OH + H—O—CH 3 Propanoic acid Methanol H+ O CH 3—CH 2—C—O—CH 3 + H 2 O Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc.

Naming Esters 33 The name of an ester consists of two words derived from the name of the alcohol and the acid in that ester. 1. The first word indicates the alkyl part from the alcohol. 2. The second word is the carboxylate name of the carboxylic acid. Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc.

Naming Esters 34 Esters have IUPAC and common names: Chemistry: An Introduction to General,

Guide to Naming Esters 35 What is the IUPAC name and common name of the following ester? O || CH 3 CH 2 C O CH 2 CH 3 Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc.

Guide to Naming Esters 36 What is the IUPAC name of the following ester? Step 1 Write the name of the carbon chain from the alcohol as an alkyl group. O || CH 3 CH 2 C O CH 2 CH 3 ethyl Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc.

Guide to Naming Esters 37 What is the IUPAC name of the following ester? Step 2 Change the -ic acid of the acid name to -ate. O || CH 3 CH 2 C O CH 2 CH 3 ethyl butanoate Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc.

Learning Check 38 Give the IUPAC and common names of the following compound, which is responsible for the flavor and odor of pears. O CH 3 — C—O—CH 2—CH 3 Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc.

Solution 39 Give the IUPAC and common names of the following compound, which is responsible for the flavor and odor of pears. Step 1 Write the name of the carbon chain from the alcohol as an alkyl group. O CH 3—C—O—CH 2—CH 3 propyl Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc.

Solution 40 Give the IUPAC and common names of the following compound, which is responsible for the flavor and odor of pears. Step 2 Change the -ic acid of the acid name to -ate. O CH 3—C—O—CH 2—CH 3 propyl ethanoate (IUPAC) propyl acetate (common) Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc.

Aspirin and Salicylic Acid 41 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 Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc.

Esters in Fruits 42 Esters give pleasant fragrances and flavors to many fruits and flowers. Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc.

Learning Check 43 Draw the structure of the following compounds. A. 3 -bromobutanoic acid B. ethyl propionoate Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc.

Solution 44 A. 3 -bromobutanoic acid Br O | || CH 3—CH—CH 2—C OH B. ethyl propionoate O CH 3—CH 2 —C—O—CH 2—CH 3 Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc.

Acid Hydrolysis of Esters 45 In acid hydrolysis, • an ester reacts with water to produce a carboxylic acid an alcohol • an acid catalyst is required O H+ H—C—O—CH 2—CH 3 + H 2 O O H—C—OH + carboxylic acid formic acid Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition H—O—CH 2—CH 3 alcohol ethanol Copyright © 2012 by Pearson Education, Inc.

Base Hydrolysis (Saponification) 46 Base hydrolysis, or saponification, • is the reaction of an ester with a strong base • produces the salt of the carboxylic acid an alcohol O || CH 3—C—O—CH 2—CH 3 + Na. OH O CH 3—C—O– Na+ + HO—CH 2—CH 3 salt of carboxylic acid alcohol sodium acetate ethanol Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc.

Base Hydrolysis of Fatty Acids Produces Soaps 47 Chemistry: An Introduction to General, Organic,

Cleaning Action of Soap 48 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 Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc.

Learning Check 49 Write the organic products when methyl acetate reacts with A. water and an acid catalyst B. KOH Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc.

Solution 50 Write the organic products when methyl acetate reacts with A. water and an acid catalyst O H+ CH 3—C—OH + HO—CH 3 B. KOH O O Heat CH 3—C—O–K+ + HO—CH 3 Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc.

Chapter 14 Carboxylic Acids, Esters, Amines, and Amides 51 14. 4 Amines Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc.

Amines 52 Amines • are derivatives of ammonia, NH 3 • contain N attached to one or more alkyl or aromatic groups CH 3—NH 2 CH 3—NH CH 3—N—CH 3 Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc.

Classification of Amines 53 Amines are classified as primary, secondary, or tertiary: • a primary (1 ) amine has one carbon group 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 | CH 3—N—H 1° CH 3 | CH 3—N—H 2° Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition CH 3 | CH 3—N—CH 3 3° Copyright © 2012 by Pearson Education, Inc.

Skeletal Structures of Amines 54 The skeletal structures show the shapes of amine molecules with one or more alkyl groups bonded to the nitrogen atom. Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc.

Naming Amines 55 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 CH 3—CH 2—NH 2 Ethylamine CH 3—NH—CH 3 Dimethylamine CH 3 | CH 3—N—CH 2—CH 3 Ethyldimethylamine Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc.

Learning Check 56 Give the common name and classify as primary, secondary, or tertiary. A. CH 3—CH 2—NH 2 CH 3 | B. CH 3—CH 2—N—CH 3 Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc.

Solution 57 A. CH 3—CH 2—NH 2 propylamine, 1 B. CH 3 | CH 3—CH 2—N—CH 3 ethyldimethylamine, 3 Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc.

Aromatic Amines 58 • • The amine of benzene is named aniline. Alkyl groups on the N use the prefix N− with alkyl name. N-methylaniline Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition 3 -chloroaniline Copyright © 2012 by Pearson Education, Inc.

Learning Check 59 Give the common name of each compound. A. CH 3—NH—CH 2—CH 3 B. CH 3 | CH 3—CH 2—N—CH 2—CH 3 Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition C. Copyright © 2012 by Pearson Education, Inc.

Solution 60 Give the common name of each compound. A. CH 3—NH—CH 2—CH 3 ethylmethylamine B. CH 3 | CH 3—CH 2—N—CH 2—CH 3 diethylmethylamine Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition C. aniline Copyright © 2012 by Pearson Education, Inc.

Properties of Amines 61 1 and 2 amines can form hydrogen bonds with each other and water molecules • can form hydrogen bonds, while amines with less than six carbons are soluble in water because they form hydrogen bonds with water 3 amines can only form hydrogen bonds with water molecules • Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc.

Learning Check 62 Consider the compounds below: 1. Which compound cannot form hydrogen bonds with other amines? 2. Which compound is not soluble in water? A. CH 3—CH 2—NH 2 B. CH 3—CH 2—NH—CH 3 C. CH 3—CH 2—CH 3 Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc.

Solution 63 Consider the compounds below: 1. Which compound cannot form hydrogen bonds with other amines? CH 3—CH 2—CH 3 C is an alkane, which cannot form hydrogen bonds with each other. 2. Which compound is not soluble in water? CH 3—CH 2—CH 3 C is an alkane and therefore not soluble in water. Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc.

Amines React as Bases 64 Like ammonia, amines are weak bases in water. NH 3 + H 2 O NH 4+ + OH– ammonium ion hydroxide ion CH 3—NH 2 + H 2 O CH 3—NH 3+ + methylammonium ion Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition OH– hydroxide ion Copyright © 2012 by Pearson Education, Inc.

Neutralization Forms Amine Salts 65 An amine salt • forms when amines such as those responsible the odor in fish are neutralized by acid such as citric acid in lemons • is named by replacing the amine part of the name with ammonium, followed by the name of the negative ion Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc.

Neutralization Forms Amine Salts 66 Chemistry: An Introduction to General, Organic, and Biological Chemistry,

Properties of Amine Salts 67 Amine salts are • solids at room temperature • soluble in water and body fluids • the form used for drugs Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc.

Alkaloids 68 Alkaloids are • physiologically active nitrogencontaining compounds produced by plants such as cocaine • compounds that are alkali-like or have basic characteristics like amines • used as anesthetics, as antidepressants, and in stimulants such as caffeine, and may be habit forming Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc.

Alkaloids: Cocaine 69 Cocaine is extracted from plants by reacting them with hydrochloric acid and producing cocaine hydrochloride. When cocaine hydrochloride is treated with Na. OH and ether it is called free-basing. This reaction produces “crack cocaine, ” a free amine or free base of the amine. Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc.

Heterocyclic Amines 70 A heterocyclic amine • is a cyclic compound that contains one or more nitrogen atoms in a ring • typically consists of five or six atoms in the ring with one or more nitrogen atoms Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc.

Caffeine 71 Caffeine • is a stimulant of the central nervous system • is found in coffee beans, tea, chocolate, and soft drinks Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc.

Nicotine 72 Nicotine • increases the adrenaline level in the blood • causes addiction to tobacco Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc.

Morphine and Codeine 73 Morphine and codeine are • alkaloids • obtained from the oriental poppy plant • used as painkillers • modified to make heroin Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc.

Learning Check 74 Write the structural formula for A. methylpropylamine B. 2 -chloroaniline Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc.

Solution 75 A. methylpropylamine CH 3–CH 2–NH–CH 3 B. 2 -chloroaniline Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc.

Chapter 14 Carboxylic Acids, Esters, Amines, and Amides 76 14. 5 Amides Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc.

Amides 77 Amides are derivatives of carboxylic acids in which a nitrogen group (–NH 2) replaces the –OH group of carboxylic acids. O || CH 3—C—OH O || CH 3—C—NH 2 Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc.

Preparation of Amides 78 Amides are produced by reacting a carboxylic acid with ammonia or a 1 or 2 amine with heat. Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc.

Naming Amides 79 • • For IUPAC naming, the -oic acid from the carboxylic acid name ending is replaced with -amide For common names, the -ic acid from the carboxylic acid name ending is replaced with -amide O H—C—NH 2 methanamide (IUPAC) formamide (common) O CH 3—CH 2—C—NH 2 propanamide (IUPAC) propionamide (common) Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc.

Naming Amides with N Groups 80 An alkyl group attached to the nitrogen of an amide is named with the prefix N-, followed by the alkyl name. O H │ CH 3 —C—N—CH 3 N-methylethanamide (IUPAC) N-methylacetamide (common) O H │ CH 3—CH 2 —C—N—CH 2—CH 3 N-ethylpropanamide (IUPAC) N-ethylpropionamide (common) Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc.

Aromatic Amide 81 The aromatic amine is benzamide. Benzamide Chemistry: An Introduction to General,

Learning Check 82 Give the IUPAC and common names for the following. A. O CH 3–CH 2–C–NH 2 B. O H │ CH 3–C–N–CH 2–CH 3 Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc.

Solution 83 A. O CH 3–CH 2–C–NH 2 B. O H │ CH 3–C–N–CH 2–CH 3 butanamide (IUPAC) butryamide (common) N-ethylethanamide (IUPAC) N-ethylacetamide (common) Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc.

Learning Check 84 Draw the structures of the following. A. pentanamide B. N-methylbutyramide Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc.

Solution 85 A. pentanamide O CH 3–CH 2–CH 2–C–NH 2 B. N-methylbutyramide O CH 3–CH 2–C–NH–CH 3 Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc.

Some Amides in Health and Medicine 86 • Urea is the end product of protein metabolism. • Saccharin is an artificial sweetener. • • Some amides, such as phenobarbital (Luminal) and pentobarbital (Nembutal), are barbiturates. Acetaminophen is used to reduce fever and pain. Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc.

Some Amides in Health and Medicine 87 Chemistry: An Introduction to General, Organic, and

Solubility of Amides 88 Amides with one to five carbon atoms are soluble in water because they can form hydrogen bonds with water molecules. Hydrogen bonding effects are diminished when molecules have more than five carbon atoms, therefore reducing solubility. Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc.

Hydrolysis of Amides 89 Amides undergo • • acid hydrolysis to produce a carboxylic acid an ammonium salt base hydrolysis to produce the salt of a carboxylic acid an amine or ammonia Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc.

Hydrolysis Reactions 90 Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition

Learning Check 91 Write the products of the hydrolysis of N-ethylpropanamide with Na. OH. Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc.

Solution 92 Write the products of the hydrolysis of N-ethylpropanamide with Na. OH. O CH 3—CH 2—C—NH CH 2—CH 3 + Na. OH O CH 3—CH 2—C—O– Na+ + CH 3—CH 2—NH 2 Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc.