Chemistry A2 Tutorial 2:

Phenol + Carboxylic acid & its derivatives

Question 1
Name the following molecules
Structural formula

Systematic name

Phenol

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Chem A2 Tutorial 2 Phenol

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Chem A2 Tutorial 2 Phenol

Question 2

a) Based on the reaction shown

(i)
Name the two types of reaction
..1
..1
(ii)

State the reagents and conditions for this change

..1
..1
(iii)
Write a balanced equation for this reaction.

..1

b) Based on the reaction shown

(i)
Name the type of reaction
..1
(ii)

State the reagents and conditions for this change

..1
(iii)

Write a balanced equation for this reaction.

..1

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Chem A2 Tutorial 2 Phenol


c) Based on the reaction shown
(i)
Name the type of reaction
..1
(ii)

State the reagents and conditions for this change

..1
(iii)
Write a balanced equation for this reaction.

..1
(iv)
Give two observations for this reaction.

..1

d) Based on the reaction shown

(i)
Name the type of reaction
..1
(ii)

State the reagents and conditions for this change

..1
(iii)
Write a balanced equation for this reaction.

..1
(iv)
Give one observation for this reaction.

..1
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Chem A2 Tutorial 2 Phenol

e) Based on the reaction shown

(i)
Name the type of reaction
..1
(ii)

State the reagents and conditions for this change

..1
(iii)
Write a balanced equation for this reaction.

..1

f) Based on the reaction shown

(i)
Name the type of reaction
..1
(ii)

State the reagents and conditions for this change

..1
(iii)
Write a balanced equation for this reaction.

..1

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Chem A2 Tutorial 2 Phenol

Step 1

Phenol

Phenoxide ion

Step 2

Phenyl carboxylate
g) Based on the reactionin step 1 and 2, that is shown above
(i)
Name the type of reaction that occurs in step 1
..1
(ii)

State the reagents and conditions for step 1.

..1
(iii)
Name the type of reaction that occurs in step 2.
..1
(iv)
State the reagent and condition for step 2.
...1
(v)
Write a balanced equation for step 1.
...1
(vi)
Write a balanced equation for step 2.
....1
Phenyl ethanoate
CH3COOC6H5

h) Based on the reaction shown above

(i)
In the table above, draw the skeletal formula of phenyl ethanoate.
(ii)
Name the type of reaction that occurs.
..1
(iii)
State the reagents and conditions for this reaction.
..1
(iv)
Write a balanced equation for this reaction.
..1

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Chem A2 Tutorial 2 Phenol

Question 3
Phenol is a weak acid
a) Define the term weak.
1
b) Define the term acid according to BrnstedLowry theory.
1
c) Write two equation that shows that Phenol is a weak acid.
1
1
d) Describe a test that can distinguish each pair. State the reagent, condition and possible
observation to show difference clearly.
(i)
Phenol and ethanol
Reagent and condition:
Phenol:

(ii)

Ethanol:.
Phenol and Phenylethanol
Reagent and condition:
Phenol:
Phenylethanol:.

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Chem A2 Tutorial 2 Phenol

Question 4
a) Explain why phenol is more reactive than benzene in its reaction with bromine
electrophile.
..

2
b) Explain why phenol is a weaker acid than ethanoic acid.(read carboxylic acid strength in
your notes)
..

2
c) Explain why phenol is a stronger acid than ethanol.
..

2
d) Arrange water, ethanol and phenol in terms of its acid strength. Explain the difference.

Weakest acid

..

...
Strongest acid

Explanation: .

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Chem A2 Tutorial 2 Phenol

Question 5
Which of the following alcohols can give a positive observation with alkaline iodine solution?

Answer: ..

Question 6
The diagram below shows some reactions of phenol.

On the diagram above, identify suitable reagents that could be used to carry out reactions shown above.

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Chem A2 Tutorial 2 Phenol

Question 7

a) Name the two functional groups found in the molecule shown above.
(i)

(ii)
..(two words)
b) Write the molecular formula of the estradiol.
.
c) Draw the structural formula of the organic product formed when estradiol reacts with
(i)
Sodium metal at room conditions

(ii)

Sodium hydroxide at room conditions

(iii)

Ethanoic acid with drops of conc. Sulfuric acid and warmed.

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Chem A2 Tutorial 2 Phenol

(iv)

PCl5, phosphorus pentachloride at room conditions.

(v)

Acidified excess potassium dichromate(VI) and mixture warmed.

(vi)

Aqueous bromine at room conditions

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Chem A2 Tutorial 2 Phenol

Question 8
Complete the table to indicate if reaction occurs or not. If there is no reaction state clearly NR. If there is
a reaction, give the structural formula of the organic product formed.
Reagent and conditions
Br2 , Aqueous bromine, room
conditions

Phenol

Phenylethanol

NaOH, Sodium hydroxide at

room conditions

Na, Sodium solid, under room

conditions.

Acidified potassium
dichromate(VI), distilled

Alkaline iodine, I2 in NaOH

warmed

CH3COOH Ethanoic acid with

drops of concentrated sulfuric
acid, warmed

CH3COCl, Ethanoyl chloride at

room conditions

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Chem A2 Tutorial 2 Phenol

Question 9
Complete the table to indicate if reaction occurs or not. If there is no reaction state clearly NR. If there is
a reaction, give the structural formula of the organic product formed.
Reagent and conditions
Aqueous bromine, room
conditions

Phenol

1-propanol

Sodium metal, room condition

Excess acidified potassium

dichromate(VI), boiled under
reflux

Acidified potassium
dichromate(VI), distilled

Alkaline iodine, I2 in NaOH

warmed

CH3COOH Ethanoic acid with

drops of concentrated sulfuric
acid, warmed

CH3COCl, Ethanoyl chloride at

room conditions

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Chem A2 Tutorial 2 Phenol

Summary:

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Chem A2 Tutorial 2 Phenol