ORGANIC CHEMISTRY

AMINES

ELNORA LISTIANTO
NABILLA SAVITRI
WULAN SUTARDIMAN
WHAT ARE AMINES?
 WHAT ARE AMINES? SUB-TOPICS

HOW ARE AMINES NAMED?

WHAT ARE THE

CHARACTERISTICS AND
PHYSICAL PROPERTIES OF
AMINES?
WHAT ARE THE ACID-BASE
PROPERTIES OF AMINES?

WHAT ARE THE REACTIONS

OF AMINES WITH ACIDS?

HOW DO AMINES ACT AS

NUCLEOPHILES?
PRIMARY (1°) AMINE SECONDARY (2°)
–R-NH2 AMINE
–R2-NH
Amines are
compounds
derived from
ammonia by
TERTIARY (3°) AMINE replacement of QUATERNARY (4°)
–R3-N one or more H AMINE
atoms -R4N+
 Thre Classifications of Amines
ALIPHATIC HETEROCYCLIC
Nitrogen bonded to only alkyl groups Nitrogen is a member that makes up the ring
  Classified into: aliphatic OR aromatic

AROMATIC
Nitrogen bonded to aryl groups
Question 1:
Can you determine which one is
a heterocyclic aliphatic amine?
Answer:
Neither. Both are heterocyclic
aromatic amines.
Purine and Imidazole.
How Amines
are named?
Alkanamines (Aliphatic Amines)
Replacing suffix -e in parent alkane with -amine

2- Butanamine 1-Phenylethanamine
Aromatic Amines
simplest ; Aniline (C6H5NH2)
derivatives ; named with prefixes ( -o,-m,-p ) or numbers
to locate the substituent + suffix - aniline

Aniline m-chloroaniline 2-chloro-4-iodoamine

Secondary and Tertiary Amines
named N-substituted primary amine
parent amine ; largest group
amine is located using the prefix N-

N -methylbutanamine N , N -dimethyl-butanamine
 AMINES HAS
THE LOWEST
PRIORITY
than alcohol
Priority and
2-AMINOPROPANOL

carboxylic
acid

USE PREFIX
AMINO- AMINOETHANOIC ACID
COMMON NAMES

ALKYLAMINES

TERT-BUTYLAMINE DICYCLOHEXYLNAMINE

AMMONIUM SALT

TETRAMETHYLAMMONIUM CHLORIDE TETRAETHYLAMMONIUM BROMIDE

Question 2
WHAT IS THE IUPAC NAME FOR
THIS COMPOUND?
Question 2
WHAT IS THE IUPAC NAME FOR
THIS COMPOUND?

Answer : p-aminobenzoic acid

WHAT ARE THE..

Characteristics
and Physical
Properties of
Amines ?
 AMINES ARE..

POLAR SOLUBLE IN
COMPOUNDS Presentations are WATER
communication tools
that can be used as
demonstrations.

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 AMINE'S HYDROGEN BOND AND
BOILING POINT

PRIMARY AMINES SECONDARY TERTIARY AMINES

It has the highest boiling AMINES It has the smallest boiling
point and can form It has lower boiling point point and can't form
hydrogen bond. It is also than primary amines and hydrogen bond with
the most soluble amine in can form hydrogen bond. another tertiary amine.
water.
 Question 3
WHICH TYPE OF AMINE THAT HAS THE
SMALLEST BOILING POINT?

PRIMARY SECONDARY TERTIARY NONE OF

THEM
Answer :
TERTIARY AMINES
WHAT ARE THE ACID-

BASE PROPERTIES OF

AMINES?
 All amines = weak
bases.

Aqueous solutions of
amines are basic.

Proton-transfer
reaction happens
(nitrogen is a proton
acceptor).

Kb = base ionization
constant
IN SHORT,

Electron-
ALIPHATIC AROMATIC withdrawing
groups

Same base strength Weaker bases than Decrease basicity of

(pKb 3.0-4.0) & aliphatic amines substitute aromatic
slightly stronger amines by ridding N
bases than ammonia of its electron pair
WHY?
Resonance interaction of
the unshared electron pair
on N with the pi system of
the aromatic ring.

-NO2 reduces the

chances of the electron
pair on N to participate in
a reaction with an acid via
both an inductive effect
and a resonance effect
 Question 4
WHICH AMINE IS A STRONGER BASE?
1 2
 Question 4
WHICH AMINE IS A STRONGER BASE?

1 2
 How do Amines AMINES + STRONG ACIDS
React with Acid? WILL PRODUCE WATER-
SOLUBLE SALT!
 Question 5

WRITE THE PRODUCT OF

THIS REACTION!
 Question 5

WRITE THE PRODUCT OF

THIS REACTION!

Answer :
HOW DO AMINES
ACT AS
NUCLEOPHILES?
amines
are moderate
nucleophiles.
 Step 1
REACTION OF AN
ELECTROPHILE AND A
NUCLEOPHILE

nucleophile electrophile
Step 2
TAKE A PROTON AWAY

unreacted starting
material
Step 3
REACTION OF AN
ELECTROPHILE AND A
NUCLEOPHILE

unreacted starting
material
 Q U E S T I O N 6

AMINE IS
CHATEGORIZED AS ...
NUCLEOPHILE

GOOD MODERATE POOR

 A N S W E R

AMINE IS
CHATEGORIZED AS ...
NUCLEOPHILE

GOOD MODERATE POOR

thank you