Part 4 Carboxylic Acids Esters Amides Amines

Carboxylic Acids,
Esters, Amides,
Amines
1
Copyright © McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education.
17.1 Structure and Bonding (1)
Carboxylic acids are organic compounds containing
a COOH (carboxyl) group.
General structure: Example:
Carboxylic
• acids are abbreviated as RCOOH or .
2
Esters are carbonyl compounds that contain an

OR’ (alkoxy) group bonded to the carbonyl C atom.
General structure: Example:
Esters
• are abbreviated as RCOOR′ or ′.
3
Amides are carbonyl compounds that contain a

N atom bonded to the carbonyl C.
General structure:
4
Amides are classified based on the number of C

atoms bonded to the N atom
A
• primary
() amide contains 1 C
—N bond.
It
• is abbreviated as .
5
A
• secondary
() amide
contains two C—N bonds,
and is abbreviated RCONHR′.
A
• tertiary
() amide contains
three C—N bonds, and is
abbreviated .
6
A cyclic ester is called a lactone:
A cyclic amide is called a lactam:
7
Carboxylic acids, esters, and amides all contain

an acyl (RCO) group bonded to a N or O atom.
8
•The
carbonyl carbon is trigonal planar, so all
bond angles are .
O is more electronegative than C, so the

carbonyl group is polar.
•The
carbonyl O is rich and the carbonyl C is
poor .
9
17.2 Nomenclature (1)
A. Naming a Carboxylic Acid (RCOOH)
To name a carboxylic acid using the IUPAC system:
• Find the longest chain containing the COOH group.
• Change the “-e” ending of the parent alkane

to ”-oic acid”.
• Number the chain to put the COOH group at C1,
but omit “1” from the name.
• Apply all other nomenclature rules.
10
Sample Problem 17.1
Write the IUPAC name of the following carboxylic acid
11
Sample Problem 17.1
Find and name the longest chain containing

COOH.
hexane • hexanoic acid

(6C’s)
12
Sample Problem 17.1
Number and name the substituents, making sure

the COOH group is at C1.
4,5-Dimethylhexanoic acid
13
Many simple carboxylic acids are referred to by
their common names:
formic acid acetic acid benzoic acid
14
The
• carbon adjacent to the COOH is called the
(alpha) carbon.
The carbon bonded to the carbon is the (beta)

carbon.
15
B. Naming an Ester (RCOOR′)
HOW TO Name an Ester Using the IUPAC System
Example Give a IUPAC name for the ester:
Step [1] Name the R’ group bonded to the O atom as

an alkyl group.
16
HOW TO Name an Ester Using the IUPAC System
Step [2] Name the acyl group (RCO-) by:

•changing the “-ic acid” ending of the parent
carboxylic acid to “-ate”.
•this becomes the second part of the name
Answer:
ethyl acetate
acetic acid • acetate 17

Practice
1. 2.
18
C. Naming an Amide
All
• amides are named by replacing the “-oic
acid”ending of the parent carboxylic acid with “-
amide”.
19
C. Naming an Amide
HOW

•HOW TO
TO Name
Name anan
2 o
or Amide
3 o
Amide
Example Give a systematic name for each amide.
a.
20
C. Naming an Amide
HOW

•HOW TO
TO Name
Name anan
2 o or Amide
3 o
Amide
Step [1] Name the alkyl groups bonded to the N

atom.
Use the prefix “N-” preceding the name.
a.
21
C.Naming an Amide
HOW
•HOW
TO
TO Name
Name anan
2 o
or 3Amide
o
Amide
Step [2] Name the acyl group with the suffix “-amide”.
a. b.
Propanoic acid  propanamide
Answer: Answer:
N,N-Dimethylbenzamide
22
17.3 Physical Properties (1)
Carboxylic acids, esters, and amides are all polar

compounds.
•Only
carboxylic acids and and amides can
undergo intermolecular hydrogen bonding.
23
Carboxylic acids have higher boiling points than

similar alcohols because there are more hydrogen
bonding interactions possible than alcohols.
CH
• 3 CH 2 CH 2 OH

•1-propanol

bpC
more hydrogen-bonding interactions possible
higher boiling point
24
Carboxylic acids also have higher boiling points

than esters because esters are incapable of
intermolecular hydrogen bonding.
stronger intermolecular
forces higher boiling point
25
•and
amides have higher boiling points than
amides and esters because of intermolecular
hydrogen bonding.
26
17.4 Interesting Carboxylic Acids (1)
Simple
• carboxylic acids have foul or biting odors.
Formic acid is responsible for the sting of some

types of ants.
Acetic acid is the sour-tasting component of

vinegar; it can be made by air oxidation of
ethanol when wine “goes bad”.
Hexanoic acid has the foul odor of dirty socks

and locker rooms.
27
A. Skin Care Products
Several
• skin care products purported to smooth
fine lines contain -hydroxy acids.
These acids work by removing the outer, older

layer of skin cells, revealing the healthier looking,
new cells underneath. 28
B. Focus on Health & Medicine
Three common pain relievers that are also anti-
inflammatory agents contain a carboxyl group:
aspirin ibuprofen
naproxen
29
B. Focus on Health & Medicine
Pain relievers work because they block the
synthesis of prostaglandins, compounds
responsible for pain responses in the body.
Sune K. Bergström, Bengt I.

Samuelsson and John R. Vane were
awarded the Nobel Prize in
Physiology or Medicine of 1982 for
their discoveries concerning
prostaglandins, thus showing how
aspirin works. 30
17.5 Interesting Esters and Amides (1)
Many low molecular weight esters have pleasant odors:
mangoes: © CD16/Author’s Image RF; apricots: © Jupiterimages/ImageSource RF;

wintergreen plant from the genus Gaultheria: © Westend61 GmbH/Alamy
31
The amide melatonin is synthesized in brain’s pineal

gland, thought to induce sleep because it’s
production is increased by the body during the
evening.
32
The ester benzocaine is the active ingredient in

topical anesthetics.
The amide acetaminophen is a pain reliever in

Tylenol.
benzocaine acetaminophen
33
17.7 Focus on Health & Medicine (1)
In 1889, Felix
Hoffmann developed
acetylsalicylic acid.
His work was
motivated by
personal reason ; his
father suffered from
rheumatoid arthritis
was not able to
tolerate the
sweetness of sodium
salicylate.
Salicylic acid irritates mucous

membranes of the mouth and
stomach while sodium salicylate is
too sweet for some patients
34
willow tree: © National Geographic/Getty Images; meadowsweet: © Biopix. dkhttp://www.biopix.dk
35
17.8 The Conversion of Carboxylic Acids
to Esters and Amides (1)
All acyl compounds undergo a common reaction
type—substitution.
36
17.8 The Conversion of Carboxylic Acids
to Esters and Amides (2)
Carboxylic acids react with alcohols to form esters.
The OR′ group replaces the OH group.
37
17.8 The Conversion of Carboxylic Acids (1)
A. Ester Formation
Formation of an ester from carboxylic acid and alcohol is

called Fisher esterification:
38
A. Ester Formation
The Fisher esterification is an equilibrium process.

According to Le Châtelier’s principle, the reaction
is driven to the right by:
• using excess alcohol
• removing the water as it is formed
39
B. Amide Formation
•
Heating a carboxylic acid with ammonia or an
amine (or ) forms an amide.
40
B. Amide Formation
The identity of the N-compound determines the
type of amide formed.
•• Reaction
with forms a amide .
41
B. Amide Formation
•
Reaction with forms a amide (RCONHR′).
•
Reaction with forms a amide .
42
17.9 Hydrolysis of Esters and Amides (1)
A. Ester Hydrolysis
An ester reacts with water to form a carboxylic acid and
an alcohol; this is a hydrolysis reaction.
The OH group replaces the OR′ group.
43
A. Ester Hydrolysis
An example of ester hydrolysis using an acid
catalyst:
The equilibrium is driven to the right by using a

large amount of water.
44
A. Ester Hydrolysis
An example of ester hydrolysis using an aqueous
base, called saponification:
This basic hydrolysis forms the carboxylate anion

rather than the carboxylic acid product.
45
B. Amide Hydrolysis
Treatment of an amide with water in the
presence of an acid catalyst (HCl) forms a
carboxylic acid and an amine salt.
46
B. Amide Hydrolysis
Amides are also hydrolyzed in aqueous base to
form carboxylate anions and amines.
47
17.11 Focus on Health & Medicine
Penicillin
• antibiotic properties of penicillinwere first
The
discovered in 1928 by Sir Alexander Fleming.
Penicillin interfereswith the enzyme that
synthesizes bacterial cell walls, killing the
bacterium.
All penicillins contain a :
48
Common Penicillins Used Today
49
Amines
Prepared by
Harpreet Malhotra
Florida State College at Jacksonville
50
Copyright © McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education.
Amines are organic nitrogen compounds, which
are classified by the number of alkyl groups
bonded to the N atom.
• primary
A amine has 1 C • secondary
A amine has 2 C—N
—N bond, and has the bonds, and has the general
general structure . structure .
51
51
Amines are organic nitrogen compounds, which are
classified by the number of alkyl groups bonded to the
N atom.
• tertiary
A amine has 3 C—N
bond, and has the general
structure .
52
52
• , , and amine N atom has a lone pair of ,which is

The
omitted in condensed structures.
The quarternaryamine has no lone pair and bears a

positive charge.
53
53
The amine N atom can also be part of a ring in a
heterocycle.
54
54
pepper plant: © Maximillian Weinzierl/Alamy; hemlock: © D. Hurst/Alamy RF
• amine N has a trigonal pyramidal shape, with bond angles

The
of approximately .
55
55
A. Primary Amines
•amines
are named with either systematicor
common names.
To find the systematic name:

• find the longest carbon chain bonded to the amine N
atom
• change the “-e” ending of the parent alkane to “-amine”
• number and name substituents using usual rules of

nomenclature
56
56
A. Primary Amines
For the common name, name the alkyl group bonded
to the N atom with the suffix “-amine.”
CH 3 NH 2
•
Common name: Methylamine
Systematic name: Methanamine
Common name: Butylamine

Systematic name: Butan-1-amine
57
57
B. Secondary and Tertiary Amines
•and amines with identical alkyl groups are named using
the prefix “di-” or “tri-”:
58
58
• HOW
HOWTO
TOName
Nameand Amines
2o and with Different
3o Amines Alkyl
with Different
Groups
Alkyl Groups
Exampl Name
• the following
Example
e amine:
59
59
• HOW
HOWTO
TOName
Name and Amines
2o and withwith
3o Amines Different Alkyl
Different
Groups
Alkyl Groups
Step Name the longest alkyl chain bonded to

Step [1]
[1] the N atom as the parent amine.
• The longest chain has 3 C’s, so it is

named propanamine.
• The N is on C2, so it is named

propan-2-amine.
60
60
• HOW
HOWTO
TOName
Name2oand
and Amines with
3o Amines Different
with Different
Alkyl
Alkyl Groups
Groups
Step Name the other groups on the N as “N-”

Step [2]
[2] alkyl groups.
Answer:
N-Methylpropan-2-amine
61
61
C. Aromatic Amines
Amines with the N directly bonded to a benzene ring
are named as derivatives of aniline:
62
62
D. Miscellaneous Nomenclature Facts
• group is called an amino group when named as a

An
substituent.
Below are come of the common amine hetero-cycles:
63
63
• amines have very foul odors like rotting fish, urine,

Many
and bad breath.
Amines are polar molecules, containing either polar C—N
or polar H—N bonds.
and amines can have intermolecular hydrogen bonding:
64
64
•and amines have higher boiling points than compounds
that do not have intermolecular hydrogen bonding.
CH 3 CH 2 OCH 2 CH 3 CH 3 CH 2 CH 2 CH 2 NH 2 CH 3 CH 2 CH 2 CH 2 OH
•
D iethyl ether
•
𝐵utan −1 −amine
• B utan− 1− ol
bp=38 ° C bp=78 ° C bp=118 ° C
• • •
• amines have lower boiling points than alcohols, as

and
alcohols have stronger intermolecular hydrogen bonds.
65
65
•amines
have lower boiling points than or amines because
they have no N—H bonds.
66
66
Caffeine and Nicotine
Caffeine and nicotine are widely used stimulants of the
central nervous system that contain amine heterocycles.
They are naturally occurring plant alkaloids.
67
67
A. Caffeine
Caffeine is a bitter tasting amine found in coffee, tea, soft
drinks, and chocolate.
It is a mild stimulant, increasing the heart rate and
signaling for glucose production so a person feels
energetic.
The effects are temporary, so people must consume more
to maintain the same “high.”
In moderation, caffeine poses no health risks, but
pregnant and nursing women should limit their intake to
reduce exposure to the baby.
Caffeine is somewhat addicting.
68
68
A. Caffeine
Table 18.1 Average Caffeine Content in Common Foods and Drugs
Product Serving Size Caffeine (mg)

Coffee, brewed 8 oz 133
Coffee, instant 16 oz 47
Coffee, decaffeinated 8 oz 5
Tea, brewed 8 oz 53
Coca-Cola Classic 12 oz 35
Diet Coke 12 oz 47
Hershey’s Chocolate Bar 1.55 oz 9
Hershey’s Special Dark Chocolate 1.45 oz 31
Anacin 2 tablets 64
NoDoz 1 tablet 200
69
69
B. Nicotine
Nicotine is a highly toxic amine isolated from tobacco,
which acts as a stimulant in small doses.
It is the addictive compound present in inhaled tobacco
smoke.
Cigarette smoking causes lung and heart disease, cancer,
etc., and is known to be a major health risk.
Because of the powerful addictiveness of nicotine, trying to
quit smoking is very difficult.
One quitting method is a nicotine patch placed on the skin,
providing the nicotine at ever-decreasing doses until the
addiction is overcome. 70
70
B. Nicotine
71
71
tobacco plant: © Flora Torrance/Life File RF; cigarrett smoke: © Nancy R. Cohen/Getty Images RF; dried tobacco leaves: © Wayne Hutchinson/Alamy
18.8 Neurotransmitters (1)
A neurotransmitter is a chemical messenger that transmits

nerve impulses from one neuron to another.
The space between the two neurons is called a synapse.
The presynaptic neuron releases the neuro-transmitter.
The postsynaptic neuron contains the receptors that bind

the neurotransmitter.
72
72
Once the neurotransmitter is bound to the receptor, the

chemical message is delivered.
The transmitter is then degraded or returned to the

presynaptic neuron to begin the process again.
Some drugs are used to prevent the release of a

neurotransmitter or to block its binding to a receptor.
Other drugs increase the amount of neuro-transmitter

released.
73
73
74
74
A. Norepinephrine and Dopamine
75
75
These two are structurally related as they are both
synthesized from the amino acid tyrosine.
When norepinephrine levels increase, a person feels elated,

and then manic if levels go too high.
Norepinephrine is converted into adrenaline when a person

experiences fear or stress.
Dopamine affects the brain processes that control

movement, emotions, and pleasure.
Patients with Parkinson’s disease have decreased levels of

dopamine in the body.
76
76
Injecting dopamine is not a treatment for Parkinson’s
because it cannot cross the blood- brain barrier.
L-Dopa, a precursor, can be used because it does cross the

barrier into the brain where it is converted into dopamine.
Overly high levels of dopamine are unhealthy and are

associated with schizophrenia.
77
77
78
78
Dopamine plays an important role in addiction.
Drugs such as heroin, cocaine, and alcohol increase

dopamine levels and give a sensation of pleasure.
When dopamine receptors are over-stimulated, they

decrease in number and sensitivity.
The person needs to take more of the pleasure-inducing

drug to reach the same “high” sensation as before.
79
79
B. Serotonin
Serotonin is synthesized from the amino acid
tryptophan.
80
80
B. Serotonin
Serotonin is important in mood, sleep, perception,
and temperature regulation.
A deficiency of serotonin causes depression, so many

antidepressant drugs are selective serotonin reuptake
inhibitors (SSRIs).
The drugs inhibit the reuptake of serotonin by the

presynaptic neuron, effectively increasing its
concentration.
81
81
B. Serotonin
Examples of antidepressant drugs are shown below:
82
82
B. Serotonin
Improper levels of serotonin can also cause migraine
headaches.
These combine pain, nausea, and sensitivity to light
and are being combated with medicines like the ones
shown below:
83
83
B. Serotonin
Compounds bufotenin and psilocin are very similar in
structure to serotonin, and they both cause intense
hallucinations.
bufo toad: © Daniel C. Smith; mushroom: © IT Stock/age fotostock RF
84
84
C. Acetylcholine and Nicotine Addiction
Acetylcholine is a quaternary ammonium ion that serves
as a neurotransmitter between neurons and muscle cells.
85
85
C. Acetylcholine and Nicotine Addiction
At low concentrations, nicotine binds to acetyl-choline
receptors, resulting in feelings of wellbeing and alertness.
This triggers other nerve cells to release dopamine, which

increases the pleasure sensation.
A person becomes addicted to the pleasure sensation

gained from taking in nicotine.
As the dopamine receptors deplete over time, a person will

crave more nicotine to reproduce the “high” feelings.
86
86
18.9 Focus on the Human Body
Epinephrine and Related Compounds (1)
A hormone is a compound produced by an endocrine
gland, which travels through the bloodstream to a target
tissue or organ.
Epinephrine (adrenaline) is a hormone made from
norepinephrine, the neurotransmitter.
87
87
Danger or emotional stress causes the formation of
epinephrine.
The body will metabolize stored carbohydrates to form

glucose, which is further metabolized to provide an
energy boost.
The heart rate increases and lung passages are dilated.
This effect is known as a “rush of adrenaline” or “fight or

flight” response.
88
88
89
89
18.9 Focus on the Human Body (1)
A. Derivatives of 2-Phenylethylamine
A large number of physiologically active compounds are

derived from 2-phenylethylamine:
90
90
Amphetamine and methamphetamine are examples

which are powerful stimulants of the central nervous
system.
While these drugs are useful as treatment for Attention

Deficit Hyperactivity Disorder (ADHD), they are also highly
addictive and widely abused.
91
91
Pseudoephedrine, sold over the counter as Sudafed,

can be readily converted to methamphetamine.
This ingredient is being replaced by

phenylephedrine which does not undergo a similar
conversion.
92
92
B. Drugs to Treat Asthma
Drugs that are structurally similar to epinephrine are used
as bronchodilators.
They do not stimulate the heart, but they do dilate lung

tissue which helps patients with asthma breath normally.
93
93
18.10 Focus on the Health & Medicine Histamine
and Antihistamines (1)
Histamine is a biologically active amine formed in many
tissues.
Histamine is a neurotransmitter with two different receptors

(H1 and H2) with a wide range of effects on the body.
94
94
Histamine and Antihistamines (2)
Histamine dilates capillaries (vasodilator), causes the
symptoms of allergies, and stimulates the secretion of
stomach acid.
Common antihistamines block histamine uptake by binding

to the H1 receptor.
This prevents vasodilation, easing cold and allergy

symptoms, but it causes drowsiness when H1 receptors in
the brain are also blocked.
Newer antihistamines cannot cross the blood-brain barrier,

leaving brain H1 receptors open, and preventing
drowsiness.
95
95
Some common drowsiness-inducing antihistamines:
96
96
A newer antihistamine which does not cause
drowsiness (sold as Allegra):
97
97
Drugs that bind to the H2 receptor product a different
effect.
For example, cimetidine, which is sold as Tagamet,

reduces stomach acid secretion, and is therefore an anti-
ulcer medication.
98
98

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Carboxylic Acids,

General structure: Example:

Esters are carbonyl compounds that contain an

General structure: Example:

Amides are carbonyl compounds that contain a

Amides are classified based on the number of C

A cyclic ester is called a lactone:

A cyclic amide is called a lactam:

Carboxylic acids, esters, and amides all contain

O is more electronegative than C, so the

• Change the “-e” ending of the parent alkane

Sample Problem 17.1

Write the IUPAC name of the following carboxylic acid

Sample Problem 17.1

Find and name the longest chain containing

hexane • hexanoic acid

Sample Problem 17.1

Number and name the substituents, making sure

formic acid acetic acid benzoic acid

The carbon bonded to the carbon is the (beta)

Example Give a IUPAC name for the ester:

Step [1] Name the R’ group bonded to the O atom as

Step [2] Name the acyl group (RCO-) by:

acetic acid • acetate 17

Example Give a systematic name for each amide.

Step [1] Name the alkyl groups bonded to the N

Propanoic acid  propanamide

Carboxylic acids, esters, and amides are all polar

Carboxylic acids have higher boiling points than

Carboxylic acids also have higher boiling points

Formic acid is responsible for the sting of some

Acetic acid is the sour-tasting component of

Hexanoic acid has the foul odor of dirty socks

These acids work by removing the outer, older

Sune K. Bergström, Bengt I.

mangoes: © CD16/Author’s Image RF; apricots: © Jupiterimages/ImageSource RF;

The amide melatonin is synthesized in brain’s pineal

The ester benzocaine is the active ingredient in

The amide acetaminophen is a pain reliever in

Salicylic acid irritates mucous

Carboxylic acids react with alcohols to form esters.

The OR′ group replaces the OH group.

Formation of an ester from carboxylic acid and alcohol is

The Fisher esterification is an equilibrium process.

• removing the water as it is formed

The OH group replaces the OR′ group.

The equilibrium is driven to the right by using a

This basic hydrolysis forms the carboxylate anion

• , , and amine N atom has a lone pair of ,which is

The quarternaryamine has no lone pair and bears a

• amine N has a trigonal pyramidal shape, with bond angles

To find the systematic name:

• number and name substituents using usual rules of

Common name: Butylamine

Step Name the longest alkyl chain bonded to

• The longest chain has 3 C’s, so it is

• The N is on C2, so it is named

Step Name the other groups on the N as “N-”

• group is called an amino group when named as a

• amines have very foul odors like rotting fish, urine,

• amines have lower boiling points than alcohols, as

Table 18.1 Average Caffeine Content in Common Foods and Drugs

Product Serving Size Caffeine (mg)

A neurotransmitter is a chemical messenger that transmits