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Chemistry of Amines
Chemistry of Amines
Chemistry of Amines
THE CHEMISTRY
OF AMINES
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KNOCKHARDY PUBLISHING
AMINES
INTRODUCTION
This Powerpoint show is one of several produced to help students understand
selected topics at AS and A2 level Chemistry. It is based on the requirements of
the AQA and OCR specifications but is suitable for other examination boards.
Individual students may use the material at home for revision purposes or it may
be used for classroom teaching if an interactive white board is available.
Accompanying notes on this, and the full range of AS and A2 topics, are available
from the KNOCKHARDY SCIENCE WEBSITE at...
www.knockhardy.org.uk/sci.htm
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AMINES
CONTENTS
• Prior knowledge
• Structure and classification
• Nomenclature
• Physical properties
• Basic properties
• Nucleophilic properties
• Amino acids
• Peptides and proteins
• Amides
• Check list
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AMINES
Before you start it would be helpful to…
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STRUCTURE & CLASSIFICATION
Classification H H
R N: R N:
H R
primary (1°) amines secondary (2°) amines
R R
R N: R N
+ R
R R
C2H5NH2 ethylamine
(CH3)2NH dimethylamine
(CH3)3N trimethylamine
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PREPARATION
Product Amine (or its salt due to a reaction with the acid produced)
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PREPARATION
Product Amine (or its salt due to a reaction with the acid produced)
Using excess ammonia ensures that all the halogenoalkane molecules react with the
ammonia before having the chance to react with any amines produced.
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PHYSICAL PROPERTIES
The LONE PAIR on the nitrogen atom in 1°, 2° and 3° amines makes them ...
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PHYSICAL PROPERTIES
Quarternary ammonium
salts are ionic and exist as salts
Bases The lone pair on the nitrogen atom makes amines basic;
Strength depends on the availability of the lone pair and its ability to pick up protons
• the greater the electron density on the N, the better it can pick up protons
• this is affected by the groups attached to the nitrogen
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BASIC PROPERTIES
Bases The lone pair on the nitrogen atom makes amines basic;
Strength depends on the availability of the lone pair and its ability to pick up protons
• the greater the electron density on the N, the better it can pick up protons
• this is affected by the groups attached to the nitrogen
H
electron withdrawing substituents (benzene rings)
decrease basicity as the electron density on N is C 6H 5 N:
lowered and the lone pair is less effective
H
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BASIC PROPERTIES
Bases The lone pair on the nitrogen atom makes amines basic;
Strength depends on the availability of the lone pair and its ability to pick up protons
• the greater the electron density on the N, the better it can pick up protons
• this is affected by the groups attached to the nitrogen
H
electron withdrawing substituents (benzene rings)
decrease basicity as the electron density on N is C 6H 5 N:
lowered and the lone pair is less effective
H
H
electron releasing substituents (CH3 groups)
increase basicity as the electron density is CH3 N:
increased and the lone pair is more effective
H
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BASIC PROPERTIES
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CHEMICAL REACTIONS - WEAK BASES
Addition of aqueous sodium hydroxide liberates the free base from its salt
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CHEMICAL REACTIONS - NUCLEOPHILIC
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NUCLEOPHILIC SUBSTITUTION
HALOALKANES
Amines are also nucleophiles (lone pair on N) and can attack halogenoalkanes to
produce a 2° amine. This too is a nucleophile and can react further producing a 3°
amine and, eventually an ionic quarternary ammonium salt.
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NUCLEOPHILIC SUBSTITUTION
HALOALKANES
Amines are also nucleophiles (lone pair on N) and can attack halogenoalkanes to
produce a 2° amine. This too is a nucleophile and can react further producing a 3°
amine and, eventually an ionic quarternary ammonium salt.
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NUCLEOPHILIC SUBSTITUTION
HALOALKANES
Amines are also nucleophiles (lone pair on N) and can attack halogenoalkanes to
produce a 2° amine. This too is a nucleophile and can react further producing a 3°
amine and, eventually an ionic quarternary ammonium salt.
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NUCLEOPHILIC SUBSTITUTION
HALOALKANES
Amines are also nucleophiles (lone pair on N) and can attack halogenoalkanes to
produce a 2° amine. This too is a nucleophile and can react further producing a 3°
amine and, eventually an ionic quarternary ammonium salt.
Uses Quarternary ammonium salts with long chain alkyl groups are used
as cationic surfactants in fabric softening e.g. [CH3(CH2)17]2N+(CH3)2 Cl¯
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AMINO ACIDS
H H
H CH3
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AMINO ACIDS – OPTICAL ISOMERISM
H
Glycine doesn’t exhibit optical isomerism as
there are two H attached to the C atom
H2N C COOH
H
GLYCINE
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AMINO ACIDS - ZWITTERIONS
R1
H3N+ C COO¯
R2
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AMINO ACIDS - ACID-BASE PROPERTIES
R1
H2N C COOH
R2
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AMINO ACIDS - ACID-BASE PROPERTIES
Basic properties:
Acidic properties:
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PEPTIDES - FORMATION & STRUCTURE
Amino acids can join together to form peptides via an amide or peptide link
a dipeptide
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PEPTIDES - HYDROLYSIS
Peptides are broken down into their constituent amino acids by hydrolysis
Peptides are broken down into their constituent amino acids by hydrolysis
H H CH3
H2N C CO NH C CO NH C COOH
CH3 H CH3
Peptides are broken down into their constituent amino acids by hydrolysis
H H CH3
H2N C CO NH C CO NH C COOH
CH3 H CH3
H H CH3
CH3 H CH3
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PEPTIDES - HYDROLYSIS
Peptides are broken down into their constituent amino acids by hydrolysis
H H H
H2N C CO NH C CO NH C COOH
CH3 H CH3
Peptides are broken down into their constituent amino acids by hydrolysis
H H H
H2N C CO NH C CO NH C COOH
CH3 H CH3
H H
CH3 H
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PROTEINS
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AMIDES
Hydrolysis
general reaction CH3CONH2 + H2O ——> CH3COOH + NH3
acidic soln. CH3CONH2 + H2O + HCl ——> CH3COOH + NH4Cl
alkaline soln. CH3CONH2 + NaOH ——> CH3COONa + NH3
Reduction
Reduced to primary amines: CH3CONH2 + 4[H] ——> CH3CH2NH2 + H2O
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AN INTRODUCTION TO
THE CHEMISTRY
OF AMINES
THE END
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