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THE ACIDITY OF PHENOL

This page explains why phenol is a weak acid and looks at its
reactions (or in some cases, lack of reaction) with bases and with
sodium metal.

Why is phenol acidic?

Compounds like alcohols and phenol which contain an -OH group


attached to a hydrocarbon are very weak acids. Alcohols are so
weakly acidic that, for normal lab purposes, their acidity can be
virtually ignored.

However, phenol is sufficiently acidic for it to have recognisably


acidic properties - even if it is still a very weak acid. A hydrogen ion
can break away from the -OH group and transfer to a base.

For example, in solution in water:

Phenol is a very weak acid and the position of equilibrium lies well
to the left.

Phenol can lose a hydrogen ion because the phenoxide ion formed
is stabilised to some extent. The negative charge on the oxygen
atom is delocalised around the ring. The more stable the ion is, the
more likely it is to form.

One of the lone pairs on the oxygen atom overlaps with the
delocalised electrons on the benzene ring.
This overlap leads to a delocalisation which extends from the ring
out over the oxygen atom. As a result, the negative charge is no
longer entirely localised on the oxygen, but is spread out around
the whole ion.

Spreading the charge around makes the ion more stable than it
would be if all the charge remained on the oxygen.

However . . . oxygen is the most electronegative element in the ion


and the delocalised electrons will be drawn towards it. That means
that there will still be a lot of charge around the oxygen which will
tend to attract the hydrogen ion back again.

That's why phenol is only a very weak acid.


Note: You will find more about the acidity of phenol,
including a comparison between it and other things like
carboxylic acids and alcohols on a page about organic
acids in a different part of the site. You will also find links
from that page to pages about the structure of benzene if
that is worrying you.

If you follow this link, you may have to explore several


other pages before you are ready to come back here
again. Use the BACK button (or HISTORY file or GO
menu) on your browser to return to this page.
Properties of phenol as an acid

With indicators

The pH of a typical dilute solution of phenol in water is likely to be


around 5 - 6 (depending on its concentration). That means that a
very dilute solution isn't really acidic enough to turn litmus paper
fully red. Litmus paper is blue at pH 8 and red at pH 5. Anything in
between is going to show as some shade of "neutral".

With sodium hydroxide solution

Phenol reacts with sodium hydroxide solution to give a colourless


solution containing sodium phenoxide.

In this reaction, the hydrogen ion has been removed by the strongly
basic hydroxide ion in the sodium hydroxide solution.

With sodium carbonate or sodium hydrogencarbonate

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:

• It is fairly insoluble in water.


• It reacts with sodium hydroxide solution to give a colourless
solution (and therefore must be acidic).
• It doesn't react with sodium carbonate or
hydrogencarbonate solutions (and so must be only very
weakly acidic).

With metallic sodium

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.

aromatic compound, any of a large class of compounds that includes benzene and
compounds that resemble benzene in certain of their chemical properties. Originally
applied to a small class of pleasant-smelling chemicals derived from vegetables, it now
encompasses a wide diversity of compounds with no connection to the sense of smell.
Common aromatic compounds other than benzene include toluene, naphthalene, and
anthracene (all of which are present in coal tar). Each of these compounds contains at
least one ring that consists of six carbon atoms, each joined to at least two other carbon
atoms, and each joined to adjacent carbon atoms by one single and one double bond. The
resulting hexagonal structure is characteristic of many aromatic compounds. The general
rule is that aromatic molecules have 4n + 2 delocalized electrons (where n is an integral
number). Thus the number of delocalized electrons in benzene (6), naphthalene (10), and
anthracene (14) agree with their aromatic character. On the other hand, the eight-
membered cyclic compound with four alternating double bonds (cyclooctatetraene) is not
aromatic and shows reactivity similar to alkenes. For this reason, the bonds in the
aromatic ring are less reactive than ordinary double bonds; aromatic compounds tend to
undergo ionic substitution (e.g., replacement of a hydrogen bonded to the ring with some
other group) rather than addition (which would involve breaking one of the resonant
bonds in the ring). Presence of the six-membered benzene ring is not essential for
aromatic compounds; for example, furan, a heterocyclic compound that has a five-
membered ring that includes an oxygen atom, has aromatic properties, as does pyridine, a
heterocyclic compound whose six-membered ring includes a nitrogen atom.

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