Amines.ppt CLASS XII part 1

CHEMISTRY CLASS XII
UNIT 13
ORGANIC COMPOUNDS CONTAINING NITROGEN
PART- I AMINES
Prepared by
OUTLINE
 Introduction
Structure of amine
Classification of amine
Nomenclature of amine
Method of Preparation of amines
Physical Properties of amines
Chemical properties of amines
Amines
Amines are the derivatives of ammonia,

obtained by replacement of one, two or all the
three hydrogen atoms of ammonia by alkyl
and/or aryl groups.
Structure of Amines
 Nitrogen atom in amine is trivalent and carries
an unshared pair of electrons.
 Nitrogen orbitals in amines are sp3hybridised.

Classification of amines
Amines
Primary 1°, Tertiary 3°

Secondary 2°
Classification of
amines……..
 Aliphatic amine: An amine in which nitrogen
is bonded only to alkyl groups.
CH3NH2 C2H5NH2
 Aromatic amine: An amine in which nitrogen

is bonded to one or more aryl groups.
CH3 CH3
:
NH2 N-H CH2 -N-CH3

:
:
Aniline N-Methylaniline Benzyldimethylamine
(a 1° aromatic amine)
(a 2° aromatic amine)
(a 3° aliphatic amine
Aromatic Amines
 Amino group is bonded to a benzene ring. Parent
compound is called aniline.
NH2
NH2
H3C
CH3 aniline
N
CH3
4-methylaniline
N,N-dimethylaniline
Nomenclature of amines
 Common names
 Name the alkyl or aryl groups bonded to
nitrogen, then add suffix -amine.
CH3NH2 C 2 H5NH2
Methylamine Ethylamine
NH
(CH3CH2)2NCH3
Diethylmetylamine Diphenylamine
Nomenclature
 In IUPAC system, amines are named as

alkanamines
 Aliphatic amines: replace the suffix -e of the
parent alkane by -amine.
CH3NH2 C 2 H5NH2
Methnamine Ethanamine
Common &IUPAC name of some alkylamines and
arylamines
Methods of Preparation of Amines
 By reduction of nitro compound
 By ammonolysis of alkyl halides
 By reduction of nitriles
 By reduction of amides
 By gabriel Phthalimide synthesis
 By hoffmann brommide degradation reaction
Methods of Preparation of Amines…..
 By reduction of nitro compound
 By ammonolysis of alkyl halides
Ammonium salt
 By reduction of nitriles
 By reduction of amides
 By gabriel phthalimide synthesis
 It only produces 1° amines. This method is not

suitable for 1° arylamine because aryl halide does
not give nucleophilic substitution reaction.
 Hoffmann bromamide degradation reaction
In Hofmann degradation reaction, the amine

formed has one carbon less than the parent
amide.
Physical Properties of Amines
 The lower aliphatic amines are gases with
fishy smell
 Amines with fewer than five carbons are
water-soluble
 Primary and secondary amines form hydrogen
bonds,but not tertiary amines
 Therefore order of boiling points of isomeric amines

is as follows: primary > secondary > tertiary
Chemical Reactions of Amines
Basicity of amines
Lone pair of electrons on nitrogen can accept a
proton from an acid.
Alkyl amines are usually stronger bases than
ammonia.
 Increasing the number of alkyl groups decreases
solvation of ion, but increases the availability of lone
pair on nitrogen atom.
Basicity of Amines…….
 Amines basic in nature react with acids to
form salts.
.
Basicity of Amines………
 Basic character of amines can be better understood
in terms of their Kb and pKb values
 Larger the value of Kb or smaller the value of pKb,

stronger is the base.
(a) Alkanamines verses ammonia
 Due to the electron releasing nature of alkyl

group, it (R) pushes electrons towards nitrogen
and thus makes the unshared electron pair more
available for sharing with the proton of the acid.
b) Arylamines verses ammonia
Arylamines such as aniline is weaker bases than ammonia. It
is because in aniline or other arylamines due to resonance the
lone pair of electrons are less available for protonation
On the other hand, anilinium ion obtained by accepting a

proton can have only two resonating structures
Greater the number of resonating structures, greater is the

stability hence it is less basic than ammonia
(ii) Alkylation
 All the three types of amines react with alkyl halides
to form quaternary ammonium salt as the final
product provided alkyl halide is present in excess .
Aromatic amines also undergo alkylation as given

below.
(iii)Acylation
 Aliphatic and aromatic primary and secondary
amines reacts with acid chlorides, anhydrides and
esters by nucleophilic substitution reaction .
(iv) Carbylamine Reaction
 This reaction is given only by primary
aliphatic or primary aromatic amines
C2H5NH2 + CHCl3 + 3KOH → C2H5NC + 3KCl + 3H2O

C6H5 NH2 + CHCl3 + 3KOH → C6H5NC + 3KCl + 3H2O
Reaction with nitrous acid
 Secondary and tertiary amines react with nitrous

acid in different manner. Methyl amine give
dimethyl ether with HNO2.
(vi)Reaction with benzensulphonyl chloride
[Hinsberg reagent]
 The reaction of benzenesulphonyl chloride with
primary amine yield N-ethyl benzenesulphonyl
amide.
Tertiary amines does not react with benzenesulphonyl

chloride.
(vii)Electrophilic substitution reactions
 Aniline is ortho and para directing towards
electrophilic substitution reactions
Bromination:
 Amines react with bromine water and form
yellow precipitate of 2,4,6 -tri bromoaniline
Bromination……
Nitration :
 Nitration of aniline is not possible as it is
susceptible to oxidation, thus amino group is
first protected by acetylation.
Sulphonation :
 On sulphonation, aniline gives sulphanilic acid
Summary
 Structure
 Classification
 Nomenclature
 Methods of preparation of amines
 Physical and chemical properties of
amines.
R O PUNE
HOME WORK
1.Writes short notes on the following
(i) Carbylamine reaction
(ii) Hoffman bromamide reaction
(iii) Gabriel phthalimide synthesis.
2. Aniline is less basic than ammonia.Why?
3. How will you convert aniline in to p-bromo aniline
Thanks

Amines.ppt CLASS XII part 1

Uploaded by

Copyright:

Available Formats

Amines.ppt CLASS XII part 1

Uploaded by

Document Information

Copyright

Available Formats

Share this document

Share or Embed Document

Sharing Options

Did you find this document useful?

Is this content inappropriate?

Copyright:

Available Formats

Amines.ppt CLASS XII part 1

Uploaded by

Copyright:

Available Formats

CHEMISTRY CLASS XII

Amines are the derivatives of ammonia,

 Nitrogen orbitals in amines are sp3hybridised.

Primary 1°, Tertiary 3°

 Aromatic amine: An amine in which nitrogen

NH2 N-H CH2 -N-CH3

 In IUPAC system, amines are named as

 It only produces 1° amines. This method is not

 Hoffmann bromamide degradation reaction

In Hofmann degradation reaction, the amine

 Therefore order of boiling points of isomeric amines

 Larger the value of Kb or smaller the value of pKb,

 Due to the electron releasing nature of alkyl

On the other hand, anilinium ion obtained by accepting a

Greater the number of resonating structures, greater is the

Aromatic amines also undergo alkylation as given

C2H5NH2 + CHCl3 + 3KOH → C2H5NC + 3KCl + 3H2O

 Secondary and tertiary amines react with nitrous

Tertiary amines does not react with benzenesulphonyl

You might also like