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PHENOLS

Chapter 5 covers the properties and reactions of phenols, including their nomenclature, boiling points, and acidity compared to alcohol and water. It explains the structure of phenols, their physical properties, and various chemical reactions such as nitration and halogenation. Students are expected to understand these concepts and be able to name phenolic compounds according to IUPAC rules and perform identification tests.

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117 views24 pages

PHENOLS

Chapter 5 covers the properties and reactions of phenols, including their nomenclature, boiling points, and acidity compared to alcohol and water. It explains the structure of phenols, their physical properties, and various chemical reactions such as nitration and halogenation. Students are expected to understand these concepts and be able to name phenolic compounds according to IUPAC rules and perform identification tests.

Uploaded by

spekkau
Copyright
© © All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
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CHAPTER 5

PHENOLS
Learning Outcome

• At the end of class, students should be able to:


✓ Name the phenols compounds according to IUPAC nomenclature
✓ Explain the boiling point of phenols.
✓ Compare the acidity of phenol, alcohol and water

2
INTRODUCTION
• Is an aromatic compounds containing one or more –OH
groups directly attached with carbon of benzene ring
• Simplest phenol is Carbolic Acid with the molecular
formula C6H5OH.
• Term phenol is derived from an old name of benzene
– Phene
• Phenyl : C6H5

3
Nomenclature of Phenols

• -OH group is represented as hydroxyl


• It is use as prefix, while benzene part of the molecule
is used as suffix (hydroxybenzene).

• If the hydroxyl group is the principle functional group


of a phenol, the compound can be named as a
substituted phenol – with C1 bearing the hydroxyl
group.

4
2 -methylphenol 2-chloro-3-methylphenol 2 -bromophenol

Example
5
• Relative position of substituents are indicated by
prefixes ortho, meta, and para ( o–, m–, and p–) or
by the use of number.

o-methylphenol m-methylphenol p-methylphenol


6
• Compounds with other principle functional
groups – hydroxyl group as substituent
• Example:

2-hydroxybenzoic acid 2-hydroxyacetophenone

7
8
Exercise:
• Give the IUPAC name for the following structures

9
Physical properties

• Colourless, crystalline, poisonous solid with


phenolic odor
• M.pt : 41oC and B.pt : 182oC
• Completely soluble in water above 68.5oC

10
Boiling point
• Have high b.pt due to the
presence of –OH group
• Able to form hydrogen bond
between hydroxyl group of
phenol molecules
• Much higher boiling point than
hydrocarbon with similar Mr

11
Example
Compare b.pt and m.pt of
phenol and toluene:
• Both have comparable melting Boiling
Mr (phenol – 94 g/mol ; point point
toluene – 92 g/mol) and (oC) (oC)
similar shape.
• Phenol has higher b.pt C6H5OH 40 - 43 182
and m.pt due to stronger
hydrogen bonding C6H5CH3 -95 111
compared to toluene
which has Van Der Waals
forces.
12
Acidity of phenol, alcohol & water

• Acidity phenol > water > alcohol


• stability of acid anion , acidity .
• The negative charge in alkoxide ion (RO-) is confined to oxygen
and cannot delocalised.
• Makes the alkoxide ion (RO-) less stable than hydroxide ion (OH-)
and weaker acid than water.
Acidity of phenol, alcohol & water

• The acidity of phenol is influenced by resonance effect:


• 1 lone pair of e- on the oxygen atom is delocalized into benzene ring.
• Causes phenoxide ion become more stable than alkoxide ion.

O H -
O
release proton

+ H+

Phenoxide ion
Phenoxide ion stability : resonance structure

O - O O O

- -

O δ-

δ- δ-
Example

OH

> CH3CH2-OH

Decreasing Acidity
PHENOLS
2.2: Reactions of Phenols
At the end of this class, students should be able to
:

1
Explain the chemical properties of phenol with
reference to reaction phenol with:

i Sodium

ii Sodium hydroxide

ii Nitration
i
i Halogenation
v
Phenol reactions

a) Reaction with Na

• Reaction occur at functional group –OH

OH O-Na+

+ Na + H2
Phenol reactions

b) Reaction with NaOH


• Reaction occur at functional group –OH

OH O-Na+

+ NaOH + H2O

CH3CH2OH + NaOH no reaction


Phenol reactions

c) Reaction with HNO3 (nitration)


• -OH is ortho-para director
OH OH
Dilute HNO3 NO2
+
Room temp.
OH
NO2

OH
O 2N NO2
Concentrated HNO3

NO2
Phenol reactions
d) Reaction with Bromine water, Br2(aq)
• Used as identification test for phenols.
• -OH is ortho-para director in Br2, aqueous solution
• White precipitate of 2,4,6-tribromophenol is obtained when
excess bromine water is added .
OH OH
Br Br
+ Br2 / H2O + HBr

Br
White precipitate
Phenol reactions

e) Reaction with FeCl3

• Used as identification test for phenols.


• When 2 or 3 drops iron (III) chloride solution is added, purple
complex coloration is produced.

OH OH

+ FeCl3 (aq)
FeCl3
Purple co
mplex
Exercise
Describe two chemical test which you would carry out to dis
tinguish between CH3C6H4OH and C6H5CH2OH

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