The dehydration of alcohols appears fairly commonly in
school and college chemistry courses.
Of course, dehydration
means the removal of the elements of
water from an organic molecule like an alcohol.
Several different reagents are or can be used but the
common ones are aluminium oxide, concentrated sulphuric acid or phosphoric
acid.
With aluminium oxide, Al2O3, the
apparatus used is given below:
The
problem with this and all other diagrams I can find on the Internet and in text
books is that they suggest that the amount of aluminium oxide used is far
too low.
The better method is to put the 2-3ml of alcohol in
the bottom an upright test-tube, vertical at first not horizontal.
Then you add enough mineral wool to absorb the alcohol.
After that, fill the whole tube with aluminium oxide granules leaving just enough room for the bung and delivery tube.
Now turn the test-tube horizontal and you are ready to dehydrate your alcohol.
Then you add enough mineral wool to absorb the alcohol.
After that, fill the whole tube with aluminium oxide granules leaving just enough room for the bung and delivery tube.
Now turn the test-tube horizontal and you are ready to dehydrate your alcohol.
Heating the granules not the alcohol on the mineral
wool should generate a steady flow of alkene bubbles.
But
remember the first bubbles will be air from the tube—this stops briefly and
then starts again and this gas is your alkene.
The equation is given on the diagram above.
You should be able to satisfy yourself that you can
construct these dehydration equations.
You also ought to be able to see why butan-2-ol generates a mixture of two different alkenes.
Dehydration using a
strong acid catalyst uses a different method.
The liquid alcohol is heated with the acid catalyst
and the more volatile alkene (it no
longer contains hydrogen bonds) is distilled over or collected as a gas
over water.
Advanced courses will also require you to build the reaction mechanism as here:
The stages are as follows
—Initial protonation of the alcohol —O—H by the acid
catalyst,
—Loss of the
elements of water leaving a carbocation.
—Rearrangement
of the carbocation and loss of a proton
facilitated
by the very polar acid solvent.
Test for the Alkene:
The usual test for an alkene can be used just to
confirm the product is what it is supposed to be
Add bromine water to the suspected alkene and cork and
shake the test tube.
The orange bromine water turns colourless and confirms
the presence of an alkene C=C double bond.
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