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Cape Chemistry Unit Ii Module I Alcohols and Phenol and Alkenes Worksheet and Revision Guide
Cape Chemistry Unit Ii Module I Alcohols and Phenol and Alkenes Worksheet and Revision Guide
A primary alcohol reacts with cold concentrated sulphuric acid to form alkyl hydrogensulphate :
If the alcohol is in excess and the reaction mixture is warmed to 140oC, an ether is formed
(iii) oxidation
Combustion of 1o, 2o and 3o– degradation of C skeleton CO2, H2O
Reaction with oxidants - maintain C skeleton
http://www.chemguide.co.uk/organicprops/alcohols/oxidation.html#top
With KMnO4/H+
o
1 – oxidized directly to carboxylic acid
2o - oxidized to ketones
Primary alcohol
Primary alcohol: -OH on C with 2 hydrogens attached [-OH on C attached to 1 other C]
During oxidation: [-2H] one from –OH and one other
Result – aldehyde
Secondary alcohol
With KMnO4/H+, K2Cr2O7 / H+ or Na2Cr2O7 / H+
The carbonyl carbon in a ketone does not have a hydrogen- no further oxidation (ketones resist oxidation)
Tertiary alcohol
In the formula CH3CH(OH)R: The alpha carbon is CH3. The alpha carbon is one carbon away from the
carbon with the functional group.
Stage 2: The 3 hydrogens on the alpha carbon are replaced with iodine
Example: ethanal in the presence of I2 / NaOH Tri-iodo-ethanal
Stage 3: The excess base hydrolyses the molecule and causes the C-C bond to break, releasing
triiodomethane [CHI3].
Example: Tri-iodo-ethanal in the presence of OH- Tri-iodomethane + the methoxide anion
We will take the reagents as being iodine and sodium hydroxide solution.
(e)
(f) The structure of phenol
http://www.chemguide.co.uk/organicprops/phenol/background.html#top
From Chemguide:
One of the lone pairs on the oxygen overlaps with the delocalised ring
electron system . . .
The donation of the oxygen's lone pair into the ring system increases the
electron density around the ring. That makes the ring much more reactive
than it is in benzene itself.
It also helps to make the -OH group's hydrogen a lot more acidic than it is in
alcohols.
The -OH group attached to the benzene ring in phenol has the effect of
making the ring much more reactive than it would otherwise be.
For example, as you will find below, phenol will react with a solution of
bromine in water (bromine water) in the cold and in the absence of any
catalyst. It also reacts with dilute nitric acid, whereas benzene itself needs a
nitrating mixture of concentrated nitric acid and concentrated sulphuric
acid.
http://www.chemguide.co.uk/organicprops/phenol/ring.html#top
Notice the multiple substitution around the ring - into all the activated
positions. (The 6- position is, of course, just the same as the 2- position. Both
are next door to the -OH group.)
Note: Bromine water is normally used as a test for a C=C double bond. The important
difference with phenol is the formation of a white precipitate as well as the bromine water
being decolourised.
If you choose to follow this link, use the BACK button on your browser to return to this page.
Combustion of phenol
http://www.chemguide.co.uk/organicprops/phenol/other.html#top
Phenol burns in a plentiful supply of oxygen to give carbon dioxide and water.
Phenol tends to burn in air with an extremely smoky flame - full of carbon
particles.
http://www.chemguide.co.uk/organicprops/phenol/other.html#top
You will probably remember that you can make esters from alcohols by
reacting them with carboxylic acids. You might expect phenol to be similar.
However, unlike alcohols, phenol reacts so slowly with carboxylic acids that
you normally react it with acyl chlorides (acid chlorides) or acid anhydrides
instead.
For example, benzoyl chloride has the formula C6H5COCl. The -COCl group is
attached directly to a benzene ring. It is much less reactive than simple acyl
chlorides like ethanoyl chloride.
In order to get a reasonably quick reaction with benzoyl chloride, the phenol
is first converted into sodium phenoxide by dissolving it in sodium hydroxide
solution.
The reactions of acid anhydrides are slower than the corresponding reactions
with acyl chlorides, and you usually need to warm the mixture.
Again, you can react the phenol with sodium hydroxide solution first,
producing the more reactive phenoxide ion.
If you simply use phenol and ethanoic anhydride, phenyl ethanoate is formed
together with ethanoic acid.
This reaction isn't important itself, but a very similar reaction is involved in
the manufacture of aspirin (covered in detail on another page - link below).
http://www.chemguide.co.uk/organicprops/phenol/acidity.html#top
With indicators
In this reaction, the hydrogen ion has been removed by the strongly basic
hydroxide ion in the sodium hydroxide solution.
Phenol isn't acidic enough to react with either of these. Or, looked at another
way, the carbonate and hydrogencarbonate ions aren't strong enough bases
to take a hydrogen ion from the phenol.
Unlike the majority of acids, phenol doesn't give carbon dioxide when you mix
it with one of these.
This lack of reaction is actually useful. You can recognise phenol because:
Acids react with the more reactive metals to give hydrogen gas. Phenol is no
exception - the only difference is the slow reaction because phenol is such a
weak acid.
Phenol is warmed in a dry tube until it is molten, and a small piece of sodium
added. There is some fizzing as hydrogen gas is given off. The mixture left in
the tube will contain sodium phenoxide.