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Chem mod 4 & 6
AMINES AMIDES C27
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Amines
Derived from
ammonia
in which
1
or
more H
atoms is replaced by a carbon chain or
ring
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Amines
Serotonin
Pseudoephedrine
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Amines
Neurotransmitter
Used
in
medicines
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Amine classification
Primary
Secondary
Tertiary
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Primary
amine
N
atom is attached to 1
alkyl
/
aryl
group
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Secondary amine
N atom is attached to
2 alkyl
/
acyl
groups
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Tertiary
amine
N
atom is attached to
two alkyl
/
acyl
groups
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Amine naming examples
N-methylpropylamine
N-ethyl
,
N-methyl propylamine
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Amines act as bases
Their
lone pair
of
electrons
on the
N
atom can accept a
proton
(
H+
) which can then form a
dative covalent bond
between the
lone pair
and the
proton
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Base strength of amines
Increases
if
lone pair
of
electrons
on the
nitrogen
atom are more readily avalible, which depends on the group attached to the N atom
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Preparation of aliphatic primary amines
1.
Ammonia
+
Haloalkane
→
Ammonium salt
2.
Ammonium salt
+
Alkali
(
aq
) →
Primary amine
ethanol = prevent haloalkane being substituted by h20 to create alcohol
NH3 in excess = to reduce further substitution
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Preparation of secondary and tertiary amines
1. Primary amine +
Haloalkane
→
Secondary salt
2. Secondary salt +
Alkali
→
Secondary amine
3. Secondary amine +
Haloalkane
→
Tertiary salt
4.
Tertiary salt
+
Alkali
→
Tertiary amine
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Preparation of aromatic amines
1.
Nitrobenzene
+ 6 [H] →(1=tin/reflux & 2= excess NAOH)phenylamine + H2O
A) nitrobenzene + reflux of Hcl/Tin = phenylammoniumchloride
B) phenylammoniumchloride + excess NAOH = phenylamine
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Amino acids
Have both
amine
and
carboxylic
acid
groups, so can act as both
acids
and
bases
(
amphoteric
)
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Amine group reactions
Amine group
(
NH2
) +
Acid
→
Salt
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Carboxylic acid group reactions
COOH
group +
Alkali
(aq) →
Salt
+
H2O
COOH
group +
Alcohol
→
Ester
+
H2O
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Amides
Derivatives of
carboxylic acids
and have a
N
atom
bonded to
one side
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Types of amides
Primary
amide
= one C bonded to N atom
Secondary amide = two C bonded to N atom
Tertiary amide = three C bonded to N atom
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Preparation of primary amides
Ammonia
+
Acyl chloride
→
Primary amide
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Preparation of secondary amides
Primary
amine +
Acyl chloride
→
Secondary
amide
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Stereoisomerism
Compounds with the same
structural formula
but a
different arrangement
of
atoms
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Optical
isomerism
Found in molecules with a
chiral centre
(C atom attached to
4
different atoms/groups)
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Amino acid
chirality
All amino acids contain a chiral
α-carbon
atom except
glycine
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Test for optical isomers
Optically active
isomers will
rotate plane polarised
light,
one enantiomer
rotates
clockwise
(
D
) and
one rotates anticlockwise
(
L
)
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Condensation polymerisation
The
joining
of
monomers
with the
loss
of a
small molecule
(
H2O
or
HCl
)
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Condensation
polymers
Polyesters
Polyamides
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Polyester formation
-COO-
1. Short chain ester monomers are joined to make ester linkages
2. Can be made from one monomer with two different functional groups or two different monomers each with two functional groups
COOH&OH MONOMER X2 = POLYESTER
DIOL MONOMER+ DICOOH ACID MONOMER= POLYESTER + H20
DIOL MONOMER+ DIACYL CHLORIDE MONOMER= POLYESTER + HCL
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Polyamide
formation-CONH-
1. Short chain amide monomers are joined together to make amide linkages/peptide bonds
2. Can be made from one monomer with two different functional groups or two different monomers each with two functional groups
COOH&NH2 MONOMER X2 = POLYAMIDE
DIAMINE + COOH ACID = POLYAMIDE + H20
DIAMINE + DIACYL CHLORIDE = POLYAMIDE +
HCL
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Polyesters
and
polyamides
can be
hydrolysed
using
hot alkali
(aq) or
hot acid
(HCl)
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Types of polymerisation
Addition
: Monomer has C=C double bond
Condensation
: Two monomers each with different functional groups or one monomer with 2 different functional groups
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