Amines and Amides

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Amines and Amides
Classified as 1, 2, 3
Primary
Primary
3-pentanamine
2-methyl-1-butylamine
Primary
3-methyl-3-pentanamine
Naming 1 amines Find longest C chain Replace
e with amine
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Amines and Amides contd

• Fig. 17.1
• Classification of amines is related to the
  number of R groups attached to the nitrogen atom.

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Secondary and Tertiary Amines
N-Methyl-1-ethanamine
N,N-Dimethyl-1-ethanamine

• Naming 2 and 3 amines
• Identify longest alkyl chain containing N
• Name substituents of N, preceded by N

• Amines have LOW priority
• When other functional groups are present, name as
  amino substituent

4-aminohexanoic acid
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Polyamines and Aromatic Amines
1,4-butanediamine (putrescine)
1,5-pentanediamine (cadaverine)
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Physical Properties of Amines

• More polar than hydrocarbons
• Less polar than alcohols
• Because N is less polar than O, solubility and
  boiling points are lower than corresponding
  alcohols
• H-bonds are formed, but LESS than in OH

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• Fig. 17.7
• Ammonium ion has a tetrahedral structure, as
  does the quaternary ammonium ion.

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Chemical Properties of Amines

• Amines act as WEAK BASES in water and ionize,
  making solution BASIC according to
• CH3NH2 H2O ? CH3NH3 OH-
• Amines react with acids to produce amine salts
• CH3NH2 HCl ? CH3NH3 Cl-

NOTE 4 (quaternary) amines are positively
charged DO NOT ACT AS BASES
Choline
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Medicinal Amine Salts
Cocaine HCl
Cocaine (Free base)
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Important Aromatic Amines
Purine (Adenine, Guanine) A, G
Pyrimidine (Cytosine, Thymine) C, T
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Amines and Amides contd

• Fig. 17.12
• Primary, secondary, and tertiary amines and
  amides and the H v. R relationship.

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Amides

• Amines Carboxylic Acids
• Amidation
• Amides can be 1, 2, 3

1
3
2
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Amines and Amides contd

• Fig. 17.15
• The high boiling point of amides are related to
  the numerous amide-amide hydrogen bonding
  possibilities that exist.

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Physical Properties of Amides

• Primary amides can hydrogen bond
• High Melting Points
• Secondary form less H-Bonds
• Tertiary form NONE

Hydrolysis of Amides
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Amines and Amides contd

• CAG 17.1