PHENOL

A guide for CAPE students

2015
SPECIFICATIONS
 PHENOL - REACTIONS OF THE OH GROUP

Water phenol is a weak acid

it dissolves very slightly in water to form a weak acidic solution
it is a stronger acid than aliphatic alcohols
the ring helps weaken the O-H bond and stabilises the resulting anion

C6H5OH(aq) C6H5O¯(aq) + H+(aq)

NaOH phenol reacts with sodium hydroxide to form a salt - sodium phenoxide
it is ionic and water soluble

C6H5OH(aq) + NaOH(aq) ——> C6H5O¯ Na+(aq) + H2O(l)

Sodium phenol reacts with sodium to form an ionic salt - sodium phenoxide
hydrogen is also produced
this reaction is similar to that with aliphatic alcohols such as ethanol

2C6H5OH(s) + 2Na(s) ——> 2C6H5O¯ Na+(s) + H2(g)

2.Reaction with an acyl chloride like ethanoyl chloride

Phenol reacts with ethanoyl chloride at room

temperature. Phenyl ethanoate is formed together
with hydrogen chloride gas.
3.Reaction with sodium hydroxide (note
that aliphatic alcohols do NOT react with
sodium hydroxide)

Phenols are more acidic than alcohols and thus can

react with strong bases like sodium hydroxide.
 PHENOL - REACTIONS OF THE AROMATIC RING

ELECTROPHILIC SUBSTITUTION

Bromine the OH group is electron releasing

it increases the electron density of the delocalised system
it makes substitution much easier compared to benzene
the electron density is greatest at the 2,4 and 6 positions
substitution takes place at the 2,4 and 6 positions
phenol reacts readily with bromine water WITHOUT A CATALYST
it is so easy that multiple substitution takes place
other electrophiles such as NO2+ react in a similar way
1. Reaction with brominePHENOLS
water
A white ppt is immediately formed
when
bromine water is added to a solution of
phenol in water. The bromine water
decolorises. The ppt has an antiseptic
smells of
.
 Relative acidities of Alcohols, Water and Phenols

Both ethanol and phenol dissociate into their

ethoxide and phenoxide ion respectively and
release a proton when dissolved in water
therefore both substances can act as acids.
However they have varying orders of acidity,
in fact increasing order of acidity is ethanol,
water and then phenol.
The strength as an acid depends on the stability of the anion formed

The greater the charge spread over the ion, the more stable
the ion is and the more readily it is formed. The more
stable the anion, the more readily it is formed i.e. the more
readily a proton is donated i.e. the stronger the acid.

pKa values can be used to express acidity of molecules

The smaller the value, the more acidic the substance is:
Ethanol pKa = 16.0, Water pKa = 15.7, Phenol pKa = 10.0
 REVISION CHECK
What should you be able to do?

Recall and explain the physical properties of alcohols

Recall the different structural types of alcohols
Recall the Lewis base properties of alcohols
Recall and explain the chemical reactions of alcohols
Write balanced equations representing any reactions in the section
Understand how oxidation is affected by structure
Recall how conditions and apparatus influence the products of oxidation
Explain how infrared spectroscopy can be used to differentiate between functional groups

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