AMINES AND

AMIDES
GROUP 1:
Gurang, Jenelyn
Miguel, Hanny Mae
Caya, Mari Andrea
Eltagonde, Charmainne
Delos Amantes, Jan Myonne
Geolina, Harianne
Cagud, Ashley
Servano, Ken Louie
Sion, Lorenz
 INTRODUCTION
Amines and amides can undergo various types of reactions depending on
the conditions and the nature of the reagents involved. For example, they can
undergo acid-base reactions, nucleophilic substitution, oxidation, reduction, and
many more. In some cases, the reactions of amines and amides can lead to the
formation of new carbon-nitrogen bonds, while in other cases, they can result in
the cleavage of existing carbon-nitrogen bonds.
Understanding the reactions of amines and amides is crucial for the design
and synthesis of new organic compounds with specific properties and functions.
Furthermore, these reactions have numerous applications in fields such as
medicine, materials science, and agriculture. In this context, the study of the
reactions of amines and amides is an important topic in organic chemistry that is
of great interest to chemists, biochemists, and researchers in related fields.
AMINES
Amines are organic compounds that contain at
least one nitrogen atom bonded to a carbon atom.
They can be classified as primary, secondary, or
tertiary, depending on the number of carbon atoms
bonded to the nitrogen atom. Amines are polar
molecules and can act as bases by accepting a
proton to form an ammonium ion. They have
diverse applications in fields such as
pharmaceuticals, agrochemicals, dyes, and
polymers, and are also important components of
biological molecules such as amino acids,
peptides, and neurotransmitters.
Physical Properties:
Amines have higher boiling
points and melting points compared
to hydrocarbons due to their ability
to
form hydrogen bonds.
They have a fishy odor, especially
the lower molecular weight amines.
Amines are soluble in water to
varying degrees, depending on their
size and polarity.
Nomenclature:
suffix -amide, prefix carboxamido-
Classification:
• Primary amines have one alkyl or aryl
• group attached to the nitrogen atom.
• Secondary amines have two alkyl or aryl
groups attached to the nitrogen atom.
• Tertiary amines have three alkyl or aryl
groups attached to the nitrogen atom.
Amines can also be classified as aliphatic or
aromatic based on the nature of the attached
alkyl or aryl groups. Aliphatic amines have
alkyl groups, while aromatic amines have aryl
groups attached to the nitrogen atom.
 AMINE
STRUCTURE
 REACTIONS
Amines can participate in a variety of reactions due to the
presence of the nitrogen atom and the lone pair of electrons
on it. Some important reactions of amines are:
GABRIEL SYNTHESIS
Primary amines can be synthesized by the Gabriel synthesis,
which involves the reaction of potassium phthalimide with an
alkyl halide followed by hydrolysis. In this reaction, the
nitrogen atom of the phthalimide is substituted by the alkyl
group, and the resulting phthalimide derivative is hydrolyzed to
form the primary amine.
 REACTIONS
ACID – BASE REACTION
Amines act as bases and can react with acids to form
ammonium salts. In this reaction, the nitrogen atom of the
amine accepts a proton (H+) from the acid to form an
ammonium ion.

NUCLEOPHILIC SUBSTITUTION REACTION

Amines can act as nucleophiles and can react with alkyl
halides to form alkylated amines. In this reaction, the nitrogen
atom of the amine attacks the electrophilic carbon atom of the
alkyl halide, displacing the halogen atom and forming a new
carbon-nitrogen bond.
 REACTIONS
REDUCTIVE AMINATION
Amines can be synthesized by the reaction of a carbonyl
compound (aldehyde or ketone) with an amine and a reducing
agent such as sodium cyanoborohydride. In this reaction, the
carbonyl group is reduced to a primary alcohol, and the amine
is converted to an amine functional group.
HOFMANN ELIMINATION
Tertiary amines can undergo a Hofmann elimination reaction
in the presence of excess halogen and base. In this reaction, the
nitrogen atom loses a methyl group to form an isocyanate
intermediate, which then decomposes to form a carbonyl
compound and a primary amine.
 AMIDES
Amides are organic compounds that contain a
nitrogen atom bonded to a carbonyl carbon atom
within the same molecule. They can be classified
as primary, secondary, or tertiary depending on
the number of carbon atoms bonded to the nitrogen
atom. Amides are polar molecules with higher
boiling points compared to similar-sized
hydrocarbons due to the presence of hydrogen
bonding between the amide functional groups. They
have diverse applications as solvents, plasticizers,
and intermediates in the production of
pharmaceuticals, agrochemicals, and other
chemicals
Physical Properties:
Amides are polar molecules due to the
presence of nitrogen and oxygen atoms,
and they have higher boiling points
compared to similar-sized hydrocarbons
due to hydrogen bonding between the
amide functional groups.
Amides are generally insoluble in
water, but some low-molecular-weight
amides, such as formamide and
acetamide, are soluble in water.
Amides have a characteristic odor and
are generally colorless.
Nomenclature:
suffix -amide, prefix carboxamido-
Classification:
• In primary amides, the nitrogen atom is
bonded to one carbon atom and two
hydrogen atoms. Examples of primary
amides include formamide and acetamide.
• In secondary amides, the nitrogen atom is
bonded to two carbon atoms. Examples of
secondary amides include N,N-
dimethylacetamide and N-
ethylpropanamide.
• In tertiary amides, the nitrogen atom is
bonded to three carbon atoms. Examples of
tertiary amides include N,N-
dimethylformamide and N,N-
dimethylpropionamide.
 AMIDE
STRUCTURE
 REACTIONS
Amides can undergo a variety of reactions, depending on
the nature of the reactant and the conditions of the reaction.
Some common reactions of amides includes:
HOFMANN REARRANGEMENT
Primary amides can be converted to primary amines by
treatment with chlorine or bromine in the presence of a strong
base such as sodium or potassium hydroxide. The reaction
involves a rearrangement of the amide functional group and
produces an amine with one fewer carbon atom than the
starting amide.
 REACTIONS
HYDROLYSIS
Amides can be hydrolyzed to form carboxylic acids and
amines by treatment with water or aqueous acid. The reaction
typically requires heating under reflux conditions, and primary
amides hydrolyze more readily than secondary or tertiary
amides.
REDUCTION
Amides can be reduced to primary amines by treatment with
reducing agents such as lithium aluminum hydride (LiAlH4) or
borane (BH3). The reaction typically requires an acidic workup
to protonate the amine product.
 REACTIONS
NUCLEOPHILIC SUBSTITUTION
Amides can undergo nucleophilic substitution reactions with
various nucleophiles, such as amines, alcohols, and thiols, to
form new amides or esters. The reaction is typically catalyzed
by an acid or base and can be carried out under mild
conditions.
AMIDE BOND FORMATION
Amides can be synthesized by reacting carboxylic acids or
their derivatives (such as acid chlorides or anhydrides) with
amines or ammonia. The reaction typically requires a
condensation agent such as DCC (dicyclohexylcarbodiimide)
to activate the carboxylic acid derivative and promote amide
bond formation.
REFERENCE 20.6: Reactions of Amines - Chemistry LibreTexts

S
https://www.youtube.com/watch?v=g6CNKW6GyD0
https://www.youtube.com/watch?v=NaM_1XvuyLo
What are the reactions for amines and amides? + Example (so
cratic.org)
https://www.bing.com/search?pglt=41&q=
what+are+the+reactions+of+amines+and+amides&cvid
=5900ae6405e34b2bad13a2749fa91e2a&aqs=edge..69i57j0l8
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