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Transcript of 1 Chapter 13 Carboxylic Acids, Esters, Amines, and Amides 13.1 Carboxylic Acids Copyright © 2005 by...
![Page 1: 1 Chapter 13 Carboxylic Acids, Esters, Amines, and Amides 13.1 Carboxylic Acids Copyright © 2005 by Pearson Education, Inc. Publishing as Benjamin Cummings.](https://reader035.fdocuments.net/reader035/viewer/2022062516/56649dc55503460f94ab856e/html5/thumbnails/1.jpg)
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Chapter 13 Carboxylic Acids, Esters, Amines, and Amides
13.1 Carboxylic Acids
Copyright © 2005 by Pearson Education, Inc.Publishing as Benjamin Cummings
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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
Carboxylic Acids
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Models of Carboxylic Acids
The three-dimensional models show the geometry of atoms in carboxylic acid molecules.
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The IUPAC names of carboxylic acids:
• Replace the -e in the alkane name with -oic acid.
CH4 methane HCOOH methanoic acid
CH3—CH3 ethane CH3—COOH ethanoic acid
• Number substituents from the carboxyl carbon 1.
CH3 O | ║
CH3—CH—CH2—C—OH 4 3 2 1
3-methylbutanoic acid
IUPAC Names
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Names and Sources of Some Carboxylic Acids
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Common Carboxylic Acids
Methanoic acid (formic acid)
O
║
H─C─OH
ethanoic acid (acetic acid)
O
║
CH3─C─OH
![Page 7: 1 Chapter 13 Carboxylic Acids, Esters, Amines, and Amides 13.1 Carboxylic Acids Copyright © 2005 by Pearson Education, Inc. Publishing as Benjamin Cummings.](https://reader035.fdocuments.net/reader035/viewer/2022062516/56649dc55503460f94ab856e/html5/thumbnails/7.jpg)
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Aromatic Carboxylic Acids
Benzoic acid• is the aromatic
carboxylic acid.
• locates substituents by numbering the ring from carbon 1 in the carboxyl group.
OHC
O
OHC
O
OHC
O
ClNH2
3-chlorobenzoic acid 4-aminobenzoic acid
benzoic acid
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Learning Check
Give the IUPAC names of each compound. A. CH3─CH2─COOH
CH3
|
B. CH3─CH─CH2─COOHC.
OHC
O
Br
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Solution
A. CH3─CH2─COOH propanoic acid
CH3
|
B. CH3─CH─CH2─COOH 3-methylbutanoic acid
C. 3-bromobenzoic acid OHC
O
Br
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13.2 Properties of Carboxylic Acids
Chapter 13 Carboxylic Acids, Esters, Amines and Amides
Copyright © 2005 by Pearson Education, Inc.Publishing as Benjamin Cummings
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Polarity of Carboxylic Acids
Carboxylic acids
• are strongly polar.
• have two polar groups: hydroxyl (−OH) and carbonyl (C=O).
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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.
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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
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Solubility in Water
Carboxylic acids: • form hydrogen bonds
with many water molecules.
• with 1-4 carbon atoms are very soluble in water.
Water molecules
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Boiling Points and Solubility
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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+
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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.
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Learning Check
Write the equation for the reaction of propanoic acid with
A. water
B. KOH
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Solution
Write the equation for the reaction of propanoic acid with
A. waterCH3—CH2—COOH + H2O CH3—CH2—COO– + H3O+
B. KOH CH3—CH2—COOH + KOH CH3—CH2—COO– K+ + H2O
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Chapter 13 Carboxylic Acids, Esters, Amines, and Amides
13.3 Esters
Copyright © 2005 by Pearson Education, Inc.Publishing as Benjamin Cummings
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Esters
In an ester, the H in the carboxyl group is replacedwith an alkyl group.
O
CH3 — C—O —CH3
ester group
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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)
Esterification
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Write the equation for the reaction of propanoic acid and methanol in the presence of an acid catalyst.
Learning Check
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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
Solution
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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.
CH3
O
CO
OH
O
C
OH
CH3O
O
C
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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
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Esters in Plants
Esters give flowers and fruits their pleasant fragrances and flavors.
Copyright © 2005 by Pearson Education, Inc.Publishing as Benjamin Cummings
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Learning Check
Give the IUPAC and common names of the following compound, which is responsible for the flavor and odor of pears.
O
CH3 — C—O—CH2—CH2—CH3
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29
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)
Solution
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Draw the structure of the following compounds.
A. 3-bromobutanoic acid
B. ethyl propionoate
Learning Check
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Solution
A. 3-bromobutanoic acid
Br
|
CH3—CH—CH2—COOH
B. ethyl propionoate O CH3—CH2 —C—O—CH2—CH3
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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
Acid Hydrolysis of Esters
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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
Base Hydrolysis (Saponification)
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Base Hydrolysis of Fatty Acids Produces Soaps
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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.
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Write the organic products when methyl acetate reacts withA. water and an acid catalyst.
B. KOH.
Learning Check
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Write the organic products when methyl acetate reacts withA. water and an acid catalyst.
O CH3—C—OH + HO—CH3
B. KOH. O
CH3—C—O– K+ + HO—CH3
Solution
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Chapter 13 Carboxylic Acids, Ester, Amines, and Amides
13.4 Amines
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Amines
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—CH3
NH2
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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°
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Models of Amines
The three-dimensional models show the shapes of amine molecules with one or more alkyl groups bonded to the nitrogen atom.
Copyright © 2005 by Pearson Education, Inc.Publishing as Benjamin Cummings
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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
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Give the common name and classify asprimary, secondary, or tertiary.
A. CH3—CH2—CH2—NH2
CH3
|B. CH3—CH2—N—CH3
Learning Check
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A. CH3—CH2—CH2—NH2
propylamine, 1°
CH3 |B. CH3—CH2—N—CH3
ethyldimethylamine, 3°
Solution
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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
NH2
Cl
NH2 CH3NH
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Learning Check
Give the common name of each compound.
A. CH3—NH—CH2—CH3
CH3
|
B. CH3—CH2—N—CH2—CH3
C.NH2
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Solution
A. CH3—NH—CH2—CH3 ethylmethylamine
CH3
|B. CH3—CH2—N—CH2—CH3
diethylmethylamine
C.
aniline
NH2
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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.
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Solubility in Water
Amines• with 1-5 carbon atoms are soluble in water.• form hydrogen bonds with the polar O-H bond in water.
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50
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?
B. Which compound is soluble in water?
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Solution
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
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Like ammonia, amines are weak bases in water.
NH3 + H2O NH4+ + OH–
ammonium hydroxide
CH3—NH2 + H2O CH3—NH3+ + OH–
methylammonium hydroxide
Amines React as Bases
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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
Neutralization forms Amine Salts
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Properties of Amine Salts
Amine salts are• solids at room temperature.• soluble in water and body fluids.• the form used for drugs.
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Alkaloids
Alkaloids are• physiologically active
nitrogen-containing compounds.
• obtained from plants.• used as anesthetics,
antidepressants, and in stimulants such as caffeine.
• often addictive.
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Cocaine
Cocaine is• sold illegally as the amine salt.• reacted with NaOH to produce the free amine form
known as “crack.”
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Caffeine• is a stimulant of the
central nervous system. • is found in coffee beans,
tea, chocolate, and soft drinks.
Caffeine
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Nicotine
Nicotine• increases the adrenaline level in the blood.• causes addiction to tobacco.
N
CH3
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Morphine and Codeine
Morphine and codeine are• alkaloids.• obtained from the
oriental poppy plant.• used as painkillers. • modified to make heroin.
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Learning Check
Write the structural formula for
A methylpropylamine
B. 2-chloroaniline
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Solution
A. methylpropylamine CH3–CH2–CH2–NH–CH3
B. 2-chloroaniline
NH2
Cl
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13.5 Amides
Chapter 13 Carboxylic Acids, Esters, Amines, and Amides
Copyright © 2005 by Pearson Education, Inc.Publishing as Benjamin Cummings
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In amides,• an amino group(–NH2) replaces the –OH group of
carboxylic acids. O O || ||
CH3—C—OH CH3—C—NH2
Amides
Copyright © 2005 by Pearson Education, Inc.Publishing as Benjamin Cummings
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Aromatic Amide
The aromatic amine is benzamide.
benzamide
O
CNH2
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Preparation of Amides
Amides are produced• by reacting a carboxylic acid with ammonia
or an amine (1° or 2°).• using heat. O O Heat CH3—C—OH + NH3 CH3—C—NH2 + H2O
O O Heat CH3—C—OH + CH3—NH2 CH3—C—NH—CH3 + H2O
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Amides are named as alkanamides.• IUPAC replaces –oic acid ending with –amide.• Common names replace -ic acid ending with –amide. O Methanamide (IUPAC) H—C—NH2 Formamide (common)
O Propanamide (IUPAC) CH3—CH2—C—NH2 Propionamide (common)
Naming Amides
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An alkyl group bonded to the N atom is named as N-alkyl in front of the amide name. O H │ CH3 —C—N—CH3 N-methylethanamide (IUPAC)
N-methylacetamide (common) O H │ CH3—CH2 —C—N—CH2—CH3
N-ethylpropanamide (IUPAC)N-ethylpropionamide (common)
Naming Amides with N Groups
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Learning Check
Give the IUPAC and common names for the following.
O A. CH3–CH2–CH2–C–NH2
O H │B. CH3–C–N–CH2–CH3
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Solution
O A. CH3–CH2–CH2–C–NH2
butanamide; butryamide
O H │B. CH3–C–N–CH2–CH3
N-ethylethanamide; N-ethylacetamide
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Learning Check
Draw the structures of
A. pentanamide.
B. N-methylbutyramide.
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Solution
A. pentanamide O
CH3–CH2–CH2–CH2–C–NH2
B. N-methylbutyramide O
CH3–CH2–CH2–C–NH–CH3
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Some Amides in Health and Medicine
• Urea is the end product of protein metabolism.
• Saccharin is an artificial sweetener.
• Some amides such as phenobarbital, Nembutal and Seconal are barbiturates.
• Acetaminophen is used to reduce fever and pain.
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Some Amides in Health and Medicine
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Physical Properties of Amides
Amides• that are primary (−NH2) or secondary (−NH−) form
hydrogen bonds.• that are primary have higher melting points than
secondary.• that are tertiary (no H on N) do not form hydrogen bonds
and have lower melting points.• all form hydrogen bonds with water.• with 1-5 carbon atoms are soluble in water.
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Hydrogen Bonding of Amides
O || CH3—C—N—H | H Hydrogen bonding occurs
between primary amides. O ||
CH3—C—N—H |
H
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Amides undergo• Acid hydrolysis to produce a carboxylic acid and
an ammonium salt.
• Base hydrolysis to produce the salt of a carboxylic acid and an amine or ammonia.
Hydrolysis of Amides
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acid hydrolysis O
|| O CH3—C—OH + NH4
+Cl–
|| HCl + H2O CH3—C—NH2
NaOH O ||
CH3—C—O– Na+ + NH3
base hydrolysis
Hydrolysis Reactions
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Write the products of the hydrolysis of
N-ethylpropanamide with NaOH.
Learning Check
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Write the products of the hydrolysis of
N-ethylpropanamide with NaOH.
O CH3—CH2—C—O– Na+ + CH3—CH2—NH2
Solution