1. Chemeketa Community College
Amides and Amines
Chapter 25
Larry Emme
Chemeketa Community College

2. Nitrogen-Containing Compounds
The amines and amides are the two major classes of nitrogen-containing compounds.
Amines isolated from plants form a group of compounds called alkaloids.
Quinine, caffeine
Amides are nitrogen derivatives of carboxylic acids.
Nylon, proteins

3. Amides: Nomenclature and Physical Properties

4. Carboxylic acids react with ammonia to form ammonium salts.
When heated, ammonium salts of carboxylic acids lose a molecule of water and are converted to amides:

5. IUPAC Rules for Naming Amides
The IUPAC name is based on the longest carbon chain that includes the amide group.
Drop the –oic acid ending from the corresponding IUPAC acid name.
Add the suffix –amide.

6. Naming Amides

7. Naming Amides
When the nitrogen of an amide is connected to an alkyl or aryl group, the group is named as a prefix preceded by the letter N:
N,N-dimethylethanamide

9. Physical Properties of Amides
Except for formamide (methanamide), a liquid, all other unsubstituted amides are solids at room temperature.
Many are odorless and colorless.
Low molar-mass amides are soluble in water, but solubility decreases quickly as molar-mass increases.

10. The amide functional group is polar, and nitrogen is capable of hydrogen bonding.

11. Chemical Properties of Amides

12. Hydrolysis of Amides

13. Amines: Nomenclature and Physical Properties

15. IUPAC System for Naming Amines
The IUPAC system names simple amines by using the name of the alkane (omitting the final –e) and adding the ending –amine.
CH3CH2NH2 ethanamine
CH3CH2CH2NH2 1-propanamine

16. Secondary and tertiary amines are named as N-substituted primary amines by using the longest carbon chain as the parent name.

17. Common Names of Amines

18. Heterocyclic Compounds
Ring compounds in which the atoms in the ring are not all alike are known as heterocyclic compounds.
The most common heteroatoms are oxygen, nitrogen, and sulfur.

19. Physical Properties of Amines
Amines are capable of hydrogen bonding with water.
They have odors:
Methylamine and ethylamine = strong ammoniacal odor
Trimethyamine = ‘fishy’ odor
High molar-mass amines = obnoxious odors

20. Amines are responsible for the strong odors of decaying flesh which
are produced by bacterial decomposition. Two of these compounds
are actually diamines as shown here. 20 20

21. Preparation of Amines

22. Preparation of Amines Alkylation of ammonia and amines
Reduction of amides and nitriles
Reduction of aromatic nitro compounds

23. Alkylation of Ammonia and Amines
The substitution of alkyl groups for hydrogen atoms of ammonia can be done by reacting ammonia with alkyl halides.

24. Reduction of Amides

25. Reduction of Aromatic Nitro Compounds
Nitrobenzene is reduced to aniline which is a common aromatic
amine. 25 25

26. Chemical Properties of Amines

27. Chemical Properties of Amines
Alkaline properties of amines
Salt formation
Formation of amides

28. Alkaline Properties of Amines
Amines are bases and produce OH– ions in water.

29. Salt Formation
An amine reacts with a strong acid to form a salt.

30. Formation of Amides
Amides are produced when primary and secondary amines react with acid chlorides. 30 30

31. Sources and Uses of Selected Amines

32. Many antibacterial agents include nitrogen containing compounds
such as those shown here.
Amines and amides are found in the B-complex vitamins B1 and B3. 32 32

33. Alkaloids are a class of compounds derived from plants that show
biological activity. Procaine is an example of a local anesthetic.
An alkaloid like nicotine stimulates the nervous system while the
opium alkaloids like methadone and cocaine have morphine-like
activity ( i.e. sleep inducing and analgesic properties). 33 33

34. Amphetamines are a class of compounds that stimulate the central
nervous system. Amphetamines like methamphetamine mimics the
action of epinephrine which produces a feeling of well-being and
increased alertness. 34 34

35. Barbiturates are a class of compounds that depress the central
nervous system. These sedatives contain amide groups. An example
is pentobarbital. 35 35

36. Other examples of drugs containing the amine/amide functional groups
include tranquilizers like Valium and antidepressants like Prozac. 36 36

37. The End