1. Chemeketa Community College
Chapter 14:
Carboxylic Acids,
Esters, Amines & Amides
Larry Emme
Chemeketa Community College

2. Chapter Outline Carboxylic Acids Properties of Acids Esters Amines
Amides

3. A poem by Ogden Nash The ant has made himself illustrious
Through constant industry industrious
So what?
Would you be calm and placid
If you were full of formic acid?

4. 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.
hydroxyl group or CH3COOH
carbonyl group

5. CH3—CH3 Ethane CH3—COOH Ethanoic acid
IUPAC Names
In the IUPAC names of carboxylic acids
the -e in the alkane name is replaced with -oic acid.
CH Methane HCOOH Methanoic acid
CH3—CH3 Ethane CH3—COOH Ethanoic acid
substituents are numbered from the carboxyl carbon 1.
3-methylbutanoic acid

6. Names and Sources of Some Carboxylic Acids

7. Common Names for Acids HCOOH Formic Formica (ant)
CH3COOH Acetic Acetum (sour)
CH3CH2COOH Propionic Pro (first) + Pion (fat)
CH3(CH2)2COOH Butyric Butyrum (butter)
CH3(CH2)3COOH Valeric Valere (strong)
CH3(CH2)4COOH Caproic Caper (goat)
CH3(CH2)5COOH Enanthic Vine (wine)
CH3(CH2)6COOH Caprylic Caper (goat)

8. Common Carboxylic Acids
methanoic acid (formic acid)
ethanoic acid (acetic acid)

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10. Aromatic Carboxylic Acids
Benzoic acid
is the aromatic carboxylic acid.
locates substituents by numbering the ring from carbon 1 in the carboxyl group.
3,4-Dichlorobenzoic Acid
Benzoic Acid
Para-Aminobenzoic Acid

11. Properties of Carboxylic Acids11 11

12. Polarity of Carboxylic Acids
are strongly polar.
have two polar groups:
hydroxyl (−OH) and
carbonyl (C=O). 12 12

13. Comparison of Boiling Points
Compound Molar Mass Boiling Point °C °C °C 13 13

14. Solubility in Water Carboxylic acids:
form hydrogen bonds with many water molecules.
with 1-4 carbon atoms are very soluble in water.
Water molecules 14 14

15. Acidity of Carboxylic Acids
are weak acids.
ionize in water to produce carboxylate ions
and hydronium ions. 15 15

16. 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 16

17. Monosodium glutamate (MSG, also known as sodium glutamate)

18. Esters 18 18

19. Esters In an ester, the H in the carboxyl group is replaced
with an alkyl group.
ester group 19 19

20. Esterification Esterification is the reaction of
a carboxylic acid and alcohol in the presence of an acid catalyst to produce an ester.
Ethyl acetate (an ester) 20 20

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. 21 21

22. Naming Esters -optional
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)
IUPAC: methyl ethanoate
common: methyl acetate 22 22

23. Esters in Plants
Esters give pleasant fragrances and flavors to many fruits and flowers. 23 23

24. 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—CH NaOH
 CH3—C—O– Na+ + HO—CH2—CH3
salt of carboxylic acid alcohol 24 24

25. Base Hydrolysis of Fatty Acids Produces Soaps25 25

26. 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. 26 26

27. Amines 27 27

28. Amines Amines are derivatives of ammonia, NH3.
contain N attached to one or more alkyl or aromatic groups. N H 2 28

29. 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 29 29

30. Aromatic Amines The amine of benzene is named aniline.
Alkyl groups on the N use the prefix N- with alkyl name.
aniline chloroaniline N-methylaniline
meta-chloroaniline 30 30

31. 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. 31 31

32. Solubility in Water Amines with 1-6 carbon atoms are soluble in water.
form hydrogen bonds with the polar O-H bond in water.
Copyright © by Pearson Education, Inc. 32 32

33. Amines React as Bases Like ammonia, amines are weak bases in water.
NH H2O NH OH–
ammonium hydroxide
CH3—NH H2O CH3—NH OH–
methylammonium hydroxide 33 33

34. 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 34 34

35. Properties of Amine Salts
Amine salts are
solids at room temperature.
soluble in water and body fluids.
the form used for drugs.
Ephedrine hydrochloride
Ephedrine HCl
Sudafed
Diphenhydramine hydrochloride
Diphenhydramine HCl
Benadryl 35 35

36. Alkaloids Alkaloids are
physiologically active nitrogen-containing compounds.
obtained from plants.
used as anesthetics, antidepressants, and in stimulants such as caffeine.
often addictive. 36 36

37. Cocaine Cocaine (from coca leaves ) is
sold illegally as the amine salt.
reacted with NaOH to produce the free amine form known as “crack.”
Cocaine hydrochloride
Cocaine (free base) 37 37

38. Caffeine Caffeine is a stimulant of the central nervous system.
is found in coffee beans, tea, chocolate, and soft drinks.
Caffeine 38 38

39. Nicotine Nicotine increases the adrenaline level in the blood.
causes addiction to tobacco. N C H 3 39

40. Morphine and Codeine Morphine and codeine are alkaloids.
obtained from the oriental poppy plant.
used as painkillers.
modified to make heroin.
Morphine
Codeine 40 40

41. Amides 41 41

42. Amides
In amides,
an amino group(–NH2) replaces the –OH group of carboxylic acids. 42 42

43. Aromatic Amide
The aromatic amine is benzamide.
Benzamide 43 43

44. Some Amides in Health and Medicine
Urea is the end product of protein metabolism.
Saccharin is an artificial sweetener.
Some amides such as phenobarbital, NembutalTM and SeconalTM are barbiturates.
Acetaminophen is used to reduce fever and pain. 44 44

45. Some Amides in Health and Medicine45 45

46. Physical Properties of 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. 46 46

47. Hydrogen Bonding of Amides||
CH3—C—N—H |
H Hydrogen bonding occurs
between primary amides. H 47 47

48. The End

49. End of Chapter Learning Checks Try these after you have reviewed the chapter

50. Learning Check
What primary alcohol can be oxidized to form pentanoic acid? 50

51. Learning Check Answers
What primary alcohol can be oxidized to form pentanoic acid?
1-Pentanol is a primary alcohol that oxidizes to pentanoic acid. 51

52. Learning Check
Write formulas for 3-chloro-4-methylhexanoic acid and α-aminobutyric acid. 52

53. Learning Check Answers
Write formulas for 3-chloro-4-methylhexanoic acid and α-aminobutyric acid. 53

54. Learning Check Show the organic product for the following reaction. 54

55. Learning Check Answers
Show the organic product for the following reaction.
Esterification reaction to form an ester. 55 55

56. Learning Check Give IUPAC and common names for the following esters.56 56

57. Learning Check Answers
Give IUPAC and common names for the following esters. 57 57

58. Learning Check
Classify the following amines as 1o, 2o or 3o. 58 58

59. Learning Check Answers
Classify the following amines as 1o, 2o or 3o. 59 59

60. Learning Check
Give the common name for the following amine. 60 60

61. Learning Check Answers
Give the common name for the following amine. 61 61