Making nitriles from
aldehydes and ketones
Aldehydes and ketones
undergo an addition reaction with hydrogen cyanide. The hydrogen
cyanide adds
across the carbon-oxygen double bond in the aldehyde or ketone to produce
a
hydroxynitrile. Hydroxynitriles used to be known as cyanohydrins.
For example, with
ethanal (an aldehyde) you get 2-hydroxypropanenitrile:
With propanone (a
ketone) you get 2-hydroxy-2-methylpropanenitrile:
In every example of
this kind, the -OH group will be on the number 2 carbon atom -
the one next
to the -CN group.
The reaction isn't
normally done using hydrogen cyanide itself, because this is an extremely
poisonous
gas. Instead, the aldehyde or ketone is mixed with a solution of sodium or
potassium cyanide in water to which a little sulphuric acid has been added.
The pH of
the solution is adjusted to about 4 - 5, because this gives the
fastest reaction. The
reaction happens at room temperature.
The solution will
contain hydrogen cyanide (from the reaction between the sodium or
potassium
cyanide and the sulphuric acid), but still contains some free cyanide ions.
This is important for the mechanism.
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These are useful
reactions because they not only increase the number of carbon atoms in
a
chain, but also introduce another reactive group as well as the -CN group.
The -OH group
behaves just like the -OH group in any alcohol with a similar
structure.
For example, starting
from a hydroxynitrile made from an aldehyde, you can quite easily
produce
relatively complicated molecules like 2-amino acids - the amino acids which
are
used to construct proteins.
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Sunday, 30 April 2017
Making nitriles from aldehydes and ketones
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Making nitriles from aldehydes and ketones
Making nitriles from aldehydes and ketones Aldehydes and ketones undergo an addition reaction with hydrogen cyanide....
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