Hydrocarbon Derivatives

1
Hydrocarbon Derivatives

• Amines, Amides, Amino Acids

2
Functional Group 8
Amines
3
Amines

• Contain a N
• General Format R?NH2
• -NH2 amino group (Remember, N has a bonding
  capacity of 3.)
• Since molecules can contain H bonded to N,
  hydrogen bonding occurs, but it is weaker than
  hydrogen bonding in alcohols and carboxylic
  acids.
• Amines smell really, really bad.

4
Table R
R
?

• Shows format R?N?R This is a 3? amine.
• 1? amines R?N?H
• 2? amines R?N?R

H
?
H
?
5
Naming Amines

• Find name of base hydrocarbon.
• Drop final e.
• Add -amine.
• If necessary, use a in front of name to give
  location of amino group.

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H H H H?C?C?N?H H H
?
Ethanamine
?
?
?
?
H H H H H?C?C?C?N?H H H H
?
?
?
?
1-propanamine
?
?
?
7
H H
H N H H?C?C?C?H H H H
lt
?
?
?
2-propanamine
?
?
?
CH2CH2CH2
1,3-propanediamine
?
?
NH2
NH2
8
NH2 ?
NH2 ?
CHCH2CH2CH
1,1,4,4-butanetetraamine
? NH2
? NH2
9
Examples of amines

• PABA
• Caffeine
• Novacain
• B-vitamins
• Preparation of dyes

10
Functional Group 9
Amides
11
Amides

• Contain a carbonyl group, gtCO, an amino group,
  ?NH2 group.
• The amino group is bonded to the C of the
  carbonyl group.
• Links amino acids together.

12
Table R
O
R
O


?

• General Format R?C?NH2 or R?C?NH
• Its like taking a carboxylic acid, RCOOH, and
  replacing the -OH with NH2.
• RCO-NH2. In this case, no is needed in name.
  Amide group is at end of molecule.

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Naming Amides

• Find the name of the alkane with the same of
  Cs, drop the final e, replace it with amide.

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H ?
O

H?C?C?NH2
Ethanamide
? H
O

Propanamide
CH3CH2CNH2
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Properties of Amides

• Have strong hydrogen bonding, so high boiling
  points.
• Simple amides are solids at room temp.
• Smaller amides are very soluble in water.

16
Functional Group 10
Amino Acids
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Amino Acids

• Have to recognize them.
• Contain a carboxyl group (-COOH).
• Contain an amine group (-NH2).
• Amino group is on the C next to the carboxyl
  group.
• Dont have to name them.

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NH2 ?
Amino Acids alanine
O

CH3?C?C
?
OH
NH2 ?
O
glycine

CH2?C
?
OH