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Amides and Amines Chapter 25
Larry Emme
Chemeketa Community College
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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

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Amides Nomenclature and Physical Properties
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• 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

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• IUPAC Rules for Naming Amides

1. The IUPAC name is based on the longest carbon
   chain that includes the amide group.
2. Drop the oic acid ending from the corresponding
   IUPAC acid name.
3. Add the suffix amide.

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Naming Amides
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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

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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.

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

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Chemical Properties of Amides
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Hydrolysis of Amides
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Amines Nomenclature and Physical Properties
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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

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

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Common Names of Amines
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Do You
?
N
Know
What
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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.

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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

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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.
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Preparation of Amines
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Preparation of Amines

1. Alkylation of ammonia and amines
2. Reduction of amides and nitriles
3. Reduction of aromatic nitro compounds

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Alkylation of Ammonia and Amines

• The substitution of alkyl groups for hydrogen
  atoms of ammonia can be done by reacting ammonia
  with alkyl halides.

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Reduction of Amides
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Reduction of Aromatic Nitro Compounds
Nitrobenzene is reduced to aniline which is a
common aromatic amine.
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Chemical Properties of Amines
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Chemical Properties of Amines

• Alkaline properties of amines
• Salt formation
• Formation of amides

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Alkaline Properties of Amines
Amines are bases and produce OH ions in water.
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Salt Formation

• An amine reacts with a strong acid to form a salt.

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Formation of Amides
Amides are produced when primary and secondary
amines react with acid chlorides.
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Sources and Uses of Selected Amines
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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.
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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).
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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.
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Barbiturates are a class of compounds that
depress the central nervous system. These
sedatives contain amide groups. An example is
pentobarbital.
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Other examples of drugs containing the
amine/amide functional groups include
tranquilizers like Valium and antidepressants
like Prozac.
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The End