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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.
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.
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.
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.
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.