Amines

1
Amines
2
Drawpara-hydroxy-N-methylbenzoamide
3
Amines

• Organic derivatives of ammonia

4
Ammonia

• H
• H-N
• H

5
Ammonium

• H
• H-N-H
• H

1
6
Primary Amine

• R1
• H-N
• H

7
Secondary Amine

• R1
• R2-N
• H

8
Tertiary Amine

• R1
• R2-N
• R3

9
Quaternary Amine

• R1
• R2-N-R4
• R3

1
10
Naming Amines
11
Alkyl amine

• R1
• H-N
• H

12
Methylamine

• CH3
• H-N
• H

13
Methylethylamine

• CH3
• CH3-CH2-N
• H

14
Trimethylamine

• CH3
• CH3-N
• CH3

15
Tetramethylammonium

• CH3 1
• CH3-N-CH3
• CH3

16
Trimethylammonium

• CH3 1
• CH3-N-H
• CH3

17
Common Amines
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Phenylamine or Aminobenzene
NH2
Aniline
19
N-Methylaniline
H
N-CH3
20
Diphenylamine
H N
21
Para-aminomethylbenzenepara-aminotoluenepara-met
hylanilinepara-toluidine
CH3
H2N
22
Para-aminobenzoic acid
O
NH2
C
HO
23
1,4-butyldiaminePutrescine

• H2N CH2 CH2
• CH2 CH2 NH2

24
1,5-pentyldiamineCadaverine

• H2N-(CH2)5-NH2

25
Draw N-Cyanoformamide
26
Heterocyclic Amines
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Pyrrolidine
H N
28
Pyrrole
H N
29
Piperidine
N-H
30
Pyridine
N
31
Indole
N
H
32
Purine
N
N
N H
N
33
Pyrimidine
N
N
34
Amino Acids
35
Common Amino Acid

• H
• R-C-COOH
• NH2

36
Glycine

• H
• H-C-COOH
• NH2

37
Alanine

• H
• H3C-C-COOH
• NH2

38
Phenylalanine

• H
• -CH2-C-COOH
• NH2

39
MakingAmines
40
Making Amines

• H3N X-R R-NH3 X-
• ammonia alkyl halide --gt alkylammonium
• R-NH3 X- MOH
• R-NH2 MX HOH

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Net Results

• H3N X-R MOH
• ammonia alkyl halide base--gt
• R-NH2 MX HOH
• alkyl amine salt water

42
Making Amines

• NH3 I-CH2-CH2-CH3
• KOH
• ammonia propyliodide potassium hydroxide

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Products

• H2N-CH2-CH2-CH3
• KI H2O
• propyl amine potassium iodide water

44
Polysubstituted Amines
base

• H3N X-R R-NH2
• R2
• H2NR X-R R-NH
• R2
• HNR2 X-R R-N-R3

base
base