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CHAPTER 8 Edited

The document summarizes key information about amines: - Amines are organic compounds derived from ammonia, with alkyl or aryl groups bonded to the nitrogen atom. They can be aliphatic or aromatic. - There are primary, secondary, tertiary and quaternary amines depending on the number of carbon groups attached to nitrogen. - Amines are named using IUPAC nomenclature similarly to alcohols. They have higher boiling points than similar alkanes due to hydrogen bonding. - Amines can be prepared through reduction of nitriles or amides. They react with acids, acyl chlorides, acid anhydrides and esters. Primary and secondary

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74 views

CHAPTER 8 Edited

The document summarizes key information about amines: - Amines are organic compounds derived from ammonia, with alkyl or aryl groups bonded to the nitrogen atom. They can be aliphatic or aromatic. - There are primary, secondary, tertiary and quaternary amines depending on the number of carbon groups attached to nitrogen. - Amines are named using IUPAC nomenclature similarly to alcohols. They have higher boiling points than similar alkanes due to hydrogen bonding. - Amines can be prepared through reduction of nitriles or amides. They react with acids, acyl chlorides, acid anhydrides and esters. Primary and secondary

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Syafiqah Suhaimi
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CHAPTER 9 AMINES

9.1 Introduction to Amines


9.2 Naming of Amines (IUPAC)
9.3 Physical Properties of Amines
9.4 Preparation of Amines
9.5 Reactions of Amines
9.1 Introduction to Amines
 Amines are organic compounds and
derivatives of ammonia (NH3) with one or
more alkyl or aryl groups bonded to the
nitrogen atom
 There are 2 types of amines; aliphatic and
aromatic
 Aromatic
CH3 amines haveO the amino functional CH3
group
CH3 N directlyCHbonded
2 NH2 HO to
C the benzene
NH2 ringN
H H
Aliphatic Aliphatic Aromatic Aromatic

 There Hare 3 classes


R' ofR' amines which are
1º 3º
primary
R N (1º), secondary
2º
R N R N(2º) and tertiary (3º)
H H R''
R or R' or R'' represents carbon chain
 Below are examples of primary, secondary
and tertiary amines
CH3

H CH3 N
H
CH3CH2 N N H-N(CH2CH3)2
H CH3
1º AMINE 3º AMINE 2º AMINE 2º AMINE

 Amine can also exist as quaternary (4º)


ammonium salt in which nitrogen atom is
bonded to 4 alkyl or aryl groups and has a
positiveCH
charge
3
+
CH3 N CH3 +
N
Br -
CH3 H3CH2CH2CH2C
tetramethyl ammonium ion N-butylpyridinium bromide
9.2 Naming of Amines (IUPAC)
 The IUPAC nomenclature of amines is similar to alcohol
 The longest continuous chain of carbon atoms determine
the root names
 The –e ending in the alkane name is changed to –amine
 Other substituents on the carbon chain are given numbers
and the prefix N- is used for each sunstituent on Nitrogen
 Primary amines (aliphatic)
 Primary aromatic amine (refer to naming of
arenes including priority groups)
 Aromatic and heterocyclic amines are known by
historical name
 Phenylamine is called ANILINE, for example, and
its derivatives are named as derivatives of aniline
 Secondary amine (Aliphatic and Aromatic)
 Tertiary amine (Aliphatic and Aromatic)
9.3 Physical Properties of Amines
 Primary and secondary amines have N-H
bonds, allowing them to form hydrogen bond
 Tertiary amines cannot form hydrogen
bonding because they do not have N-H bond.
They can, however, accept hydrogen bonds
from molecule having O-H or N-H bonds.
δ+
H
δ+ δ-
H :N R
δ -

R N: H
δ+
δ+H
 Amines are polar molecules; amines 1°, 2°
and 3° are soluble in water because they
form hydrogen bond with water
 Amines have higher boiling point than
alkane, alkenes, haloalkanes and carbonyl
compounds of similar relative molecular
mass. This is because amines can form
stronger hydrogen bond between
δ+ molecules
H
δ+ δ-
H N
δ- .. R
R .N. Hδ+
δ +
H
 Amines have lower boiling point than
alcohols of similar relative molecular mass
because of weaker hydrogen bond between
molecules due to nitrogen atom being less
electronegative than oxygen atom
Carboxylic acid > alcohols > amines > haloalkanes >
alkanes
Boiling point
decreasing

 For isomeric amines, the order of boiling


point is: 1°amine > 2°amine > 3°amine
Basicity
 Like ammonia (NH3), all amines are weak bases,
and aqueous solutions of amines are basic
 The following acid-base reaction between an
amine and water is written using curved arows to
emphasize that, in these proton transfer
reactions, the unshared pair of electrons on
nitrogen forms a new covalent bond with
hydrogen and displaces hydroxide ion
H H
.. + -: ..
H3C N: + H O
..
H H3C N H O-H
..
H H
Methylamine Methylammonium hydroxide
9.4 Preparation of Amines
1) Reduction of Nitriles and Amides (1°, 2°, 3°)
 Reducing agents that are suitable are LiAlH4 in
ether and H3O+, NaBH4 in H3O+, and Ni/Pt catalyst
with hydrogen gas at 170°C
9.4 Reaction of Amines
1) Reaction with acid (Neutralisation)
 Amines react with acids to form salt by donating
its electron pair on the nitrogen atom and accepts
a proton, H+ ion
+ -

methylamine Methylammonium
chloride

aniline Aniliniammonium
nitrate
2) Reaction with Acyl Chloride
(Refer to Chapter 8: Reaction of Acyl Chloride )
 Primary (1°) and secondary (2°) amines react with
acyl chloride to form 2° amide and 3° amide
 3° amines do not react with acyl chloride because it
does not have hydrogen atom directly bonded to
nitrogen atom
3) Reaction with Acid Anhydride
(Refer to Chapter 8: Reaction of Acid Anhydride)
 Primary amine react with acid anhydride to form
secondary amide whereas secondary amine react
to form tertiary amide
4) Reaction with Esters
(Refer to Chapter 8: Reaction of Ester )

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