AMINES AND AMIDES

Learning objectives
at the end of this lesson, you will be able to:
Classify amines and amides as primary, secondary, or tertiary
amines and amides.
Describe the chemical and physical properties of amines and
amides.
Be able to name amines and amides using IUPAC rules or vice versa;
know the common name system for naming simple amines and
amides.
AMINES
What is an amine?
An amine is an organic derivative of ammonia
(NH3) in which one or more alkyl, cycloalkyl, or
aryl groups have replaced ammonia hydrogen
atoms.
General Formula: R-NH2
 Physical properties of amines
Methylamines (mono-, di-, and tri-) and ethylamine are gases at
room temperature and have ammonia-like odors.
Most other amines are liquids, many have odors resembling that of
raw fish.
The simpler amines are irritating to the skin, eyes, and mucous
membranes and are toxic by ingestion.
They are higher than alkane boiling points, because primary and
secondary amines are capable of intermolecular hydrogen bonding,
whereas alkane molecules lack such ability.
 chemical properties of amines
Hydrogen bonding directly impacts the characteristics of primary and secondary amines, as well as
various amine derivatives.
While phosphorus compounds have a lower boiling point than amines, alcohol-containing
compounds have a higher boiling point.
The amines have a high water solubility because of their capacity to create hydrogen bonds.
Ethyl, triethyl, diethyl, and Methyl are gaseous amine compounds.
Higher weight amines have a solid structure, whereas alkyl amines are liquid.
A fishy smell is present in liquid amines, and an ammonia-like scent is present in gaseous ones.
Aqueous mineral acids quickly react with these amines, converting them to salts. They are freed
from their salts when they react with aqueous hydroxides. As a result, amines are more basic than
water, while hydroxide ions are less basic.
Higher-order amines are formed through the reaction of amines with alkyl halides. The nucleophilic
assault process uses the nitrogen atom as a nucleophile to attack the alkyl halide.
  lassification of amines
C

Amines are classified as primary (1°),

secondary (2°), or tertiary (3°) on the basis
of how many hydrocarbon groups have
replaced ammonia hydrogen atoms.
 Classification of amines
A primary amine is an amine in which the nitrogen atom is
bonded to one hydrocarbon group and two hydrogen atoms.
Generalized formula: RNH2
A secondary amine is an amine in which the nitrogen atom is
bonded to two hydrocarbon groups and one hydrogen atom.
Generalized formula: R2NH
A tertiary amine is an amine in which the nitrogen atom is bonded
to three hydrocarbon groups and no hydrogen atoms.
Generalized formula: R3N
 Examples
primary secondary tertiary
The functional group present in a primary amine, the
—NH2 group, is called an amino group.
Secondary and tertiary amines contain substituted
amino groups.
common nomenclature for
AMINES
common Nomenclature for amines
In common system of nomenclature, amines are named by listing
the alkyl group or groups attached to the nitrogen atom in
alphabetical order and adding the suffix -amine; all of this
appears as one word.
Prefixes such as di- and tri- are added when identical groups
are bonded to the nitrogen atom.
iupac nomenclature for
AMINES
 iupac Nomenclature for amines
The IUPAC rules for naming amines are similar to those for
alcohols. Alcohols are named as alkanols and amines are
named as alkanamines.

IUPAC nomenclature for primary amines is similar to that for

alcohols, except that the suffix is -amine rather than -ol. An
—NH2 group, like an —OH group, has priority in
numbering the parent carbon chain.
IUPAC rules for naming primary amines are as follows:

Rule 1: Select as the parent carbon chain the longest chain to

which the nitrogen atom is attached.

Rule 2: Name the parent chain by changing the -e ending of

the corresponding alkane name to -amine.

Rule 3: Number the parent chain from the end nearest the
nitrogen atom.
Rule 4: The position of
attachment of the nitrogen atom
is indicated by a number in front
of the parent chain name.

Rule 5: The identity and

location of any substituents are
appended to the front of the
parent chain name.
In diamines, the final -e of the carbon chain name is
retained for ease of pronunciation. Thus the base name
for a four-carbon chain bearing two amino groups is
butanediamine.
Secondary and tertiary amines are named as N-substituted
primary amines.
The largest carbon group bonded to the nitrogen is used as the
parent amine name.
The names of the other groups attached to the nitrogen are
appended to the front of the base name, and N- or N,N- prefixes
are used to indicate that these groups are attached to the
nitrogen atom rather than to the base carbon chain.
In amines where additional functional groups are present, the
amine group is treated as a substituent. As a substituent, an —NH2
group is called an amino group.

Note: In IUPAC nomenclature, the amino group has a priority just

below alcohol.
The simplest aromatic amine, a benzene ring bearing an amino
group, is called aniline. Other simple aromatic amines are named as
derivatives of aniline, with the carbon atom bearing the amino
group being carbon 1.
In secondary and tertiary aromatic amines, the additional group or
groups attached to the nitrogen atom are located using a capital N-.
Practice
 Practice

N-ethyl-1-pentanamine 4-bromoaniline
(or p-bromoaniline)

1,2-ethanediamine
N,N-dimethylethanamine
AMIdES
WHAT IS AN AMIDE?
An amide is a carboxylic acid derivative in which
the carboxyl —OH group has been replaced
with an amino or a substituted amino group.
General Formula: R-CO-NH-R
 PHYSICAL PROPERTIES OF AMIDEs
Methanamide and its N-methyl and N,N-dimethyl derivatives (the
simplest 1°, 2°, and 3° amides), are all liquids at room temperature.

All unbranched primary amides, except methanamide, are

solids at room temperature.
In many cases, the amide melting point is even higher than that of the
corresponding carboxylic acid. The high melting points result from the
numerous intermolecular hydrogen-bonding possibilities that
exist between amide H atoms and carbonyl O atoms.
Fewer hydrogen-bonding possibilities exist for 2° amides
because the nitrogen atom now has only one hydrogen atom;
hence lower melting points are the rule for such amides.
Still lower melting points are observed for 3° amides

because no hydrogen bonding is possible.

Amides of low molecular mass, up to five or six carbon atoms,
are soluble in water. Again, numerous hydrogen-bonding
possibilities exist between water and the amide. Even
disubstituted amides can participate in such hydrogen
bonding
 chemical PROPERTIES OF AMIDEs
Amides are the least reactive of all the acid derivatives
toward nucleophilic acyl substitution reactions.
Amides are much less basic than amines.

Amides behave both as weak bases as well as weak

acids.
Amides can be hydrolysed by boiling with water, acids
or alkalis.
 Classification of amides
A primary amide is an amide in which two hydrogen atoms are
bonded to the amide nitrogen atom. Such amides are also called
unsubstituted amides.
A secondary amide is an amide in which an alkyl (or aryl) group
and a hydrogen atom are bonded to the amide nitrogen atom,
monosubstituted amide is another name for this type of amide.
A tertiary amide is an amide in which two alkyl (or aryl) groups
and no hydrogen atoms are bonded to the amide nitrogen atom,
also called disubstituted amides.
Classification of amides
common and iupac nomenclature
for amides
 common AND IUPAC Nomenclature for amiDes

Rule 1: The ending of the name of the carboxylic acid is changed

from -ic acid (common) or -oic acid (IUPAC) to -amide. For
example, benzoic acid becomes benzamide.

Rule 2: The names of groups attached to the nitrogen (2° and 3°

amides) are appended to the front of the base name, using an N-
prefix as a locator.
Selected primary amide IUPAC names (with the common name in parentheses):
Nomenclature for secondary and tertiary amides, amides with
substituted amino groups, involves use of the prefix N-, a
practice that was previously encountered with amine
nomenclature.
Molecular models for methanamide and its N-methyl and N,N-
dimethyl derivatives (the simplest 1°, 2°, and 3° amides,
respectively).
The simplest aromatic amide, a benzene ring bearing an
unsubstituted amide group, is called benzamide. Other aromatic
amides are named as benzamide derivatives.
When an amide functional group is attached to a nonaromatic
ring, the suffix carboxamide is used in the name.
Practice
 end.
Thank you.