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Organic Chemistry Revision
Amines…read more

Slide 2

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· Primary Amine - Remove `e' and replace with amine e.
g. ethanamine and label where NH2 occurs e.g. propan-
· Secondary Amine ­ same as above for longest chain
with N in front and any other R group as an `yl' group e.
g. N-methylpropan-2-amine
· Tertiary Amine ­ same as above but add two N prefixes
· They can act as bases and nucleophiles
· They have high boiling points because of hydrogen
· Simple aliphatic amines are soluble in water because of
H bonding between the NH2 group and polar water
· All amines react with acids to form salts…read more

Slide 3

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Primary Amines from Haloalkanes
· Halogen is replaced with NH2
· Reaction is nucleophilic substitution
CH3Br + 2NH3 CH3NH2 + NH4Br
· Because of the lone pair on the nitrogen further substitution occurs to
give a mix of primary, secondary, tertiary and even quaternary ammonium
· To prevent this a high concentration of ammonia is used as the amine
competes with ammonia to react with the halogen…read more

Slide 4

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Primary Amines from Nitriles
· Made by reduction of nitriles ­ reducing
agents H2 and a nickel catalyst
· CH3CN + 4[H] CH3CH2NH2
· In the reaction the aromatic nitro compound
is protonated to form an intermediate with
· Base is added to accept the extra proton to
make NH2 group…read more

Slide 5

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Aromatic Amines
· Made by the reduction of aromatic nitro
compounds by H2 and nickel catalyst
RNO2 + 6[H] RNH2 + 2H2O…read more

Slide 6

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Amines as Bases
· Aromatic amines are weak bases because the lone
pair is not easily donated because the electrons
are part of the pi system
· Aliphatic amines are stronger bases because the
electrons are more readily available because there
is a higher electron density on the nitrogen atom
· Nitrogen atoms that are not attached directly to
the benzene ring are stronger bases as the
electrons are not part of the pi system so are
available to donate…read more


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