LEARNING

CHAPTER OUTCOMES:
8.6: PHENOL
Compare the acidity of phenol, alcohol and water.
Explain the chemical properties of phenol with reference to :
Reaction with sodium
Reaction with sodium hydroxide
Identification tests using FeCI3 solution and bromine water.

THEORY OF ACID

Acid - compound that form

H+ ions or H3O+ ions in
BRONSTED-LOWRY THEORY aqueous solution
ARRHENIUS THEORY

Acid - proton donors

Base - proton acceptor

HA + H2O A- + H3O+
Conjugate
base
ACIDITY

ACIDITY To determine the stability of the conjugate base of an acid.

Anything that stabilizes the conjugate base makes the acid more acidic.

The higher the stability of the conjugate base the higher the acidity.

COMPARISON OF ACIDITY

R – OH < Water <

Aliphatic alcohol Phenol

Acidity increases

Alcohols, water and phenols are classified as weak acid.

- THEY ARE ACID & act as proton donor in aqueous solution.

Compounds pKa Ka
Ethanol 16 1x10-16
Water 14 1x10-14
Phenol 10 1x10-10

ALIPHATIC ALCOHOL, R-OH

CHAPTER 8.0:HYDROXY COMPOUNDS_ sem 2 2018/2019_ aef Page 1

 Alkyl, R

 Aliphatic alcohol (R-OH) are less acidic than water due to presence of electron donating
group,EDG (alkyl)

 The electron donating group,EDG will increase the density of negative charge on the
-
Arrange theatom
oxygen makingbelow
compound the R-O ion less
according to stable (destabilizes)
increasing acidity compare to hydroxide ion(OH-)
R OH + H2 O R O
-
+ H3 O
+

Compounds pKa Ka
H O 2 + H2 O OH
-
+ H3 O
+

Ethanol 16 1x10-16
-
 R-O ion less stable because the negative charge is localized only on the oxygen
atom of alkoxideWater
ion 14 1x10-14
 Examples of EDG (Acidity decrease with presence of EDG)
Alkyl (R) Phenol 10 1x10-10
Hydroxyl (OH)
Amino (NH2)
 If ALCOHOL attach with electron withdrawing group, EWG, it will stabilize the
ions & increase acidity
 Examples of EWG (Acidity increase with presence of EWG)
Halogen, X Carbonyl, C=O
Carboxyl, COOH

PHENOL

 Phenol is the most acidic because the phenoxide ion is stable.

 The acidity of phenol is due to the delocalisation of the negative charge on

oxygen atom of the phenoxide ion onto the benzene ring which causes
the ion to be stabilized by the resonance effect

EXAMPLE
RESONANCE STRUCTURES

CHAPTER 8.0:HYDROXY COMPOUNDS_ sem 2 2018/2019_ aef Page 2

 Arrange the compound below according to increasing acidity

EXERCISE

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 CHEMICAL PROPERTIES OF PHENOL

CHEMICAL REACTIONS IDENTIFICATION TESTS

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 1. REACTION WITH Na 1. USING FeCl3

Observation: Purple complex formed

2. REACTION WITH NaOH
2. BROMINE WATER

Observation: Reddish brown colour of

bromine decolourised and white precipitate
formed

EXERCISES

1. Suggest a chemical test to differentiate the following pairs of compounds

a. Phenol from benzyl alcohol

Name of Test
Reagent
Chemical Reaction &
Observation
2. . The structural formula of X is shown below :

Suggest a chemical test to differentiate the following pairs of compounds

b. 1,2-ethanediol and phenol
c.
Name of Test
Reagent
Chemical Reaction &
Observation

Draw structural formula of product form when X reacts with :

a. Sodium
b. Aqueous sodium hydroxide
c. Phosphorus pentachloride
d. Propanoic acid refluxed with traces of concentrated sulfuric acid

CHAPTER 8.0:HYDROXY COMPOUNDS_ sem 2 2018/2019_ aef Page 5