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Chemistry A2 Tutorial 1:

Question 1.

Benzene and its derivatives

Complete the table below with the correct formula

Name and Molecular


formula
Benzene

Structural formula

Skeletal formula

C6H6

Methylbenzene

Ethylbenzene

Nitrobenzene

1,3-dinitrobenzene

Cyclohexane

Cyclohexene

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A2 Chemistry Tutorial 1

Empirical Formula

2.

(a)

Benzene reacts with concentrated nitric acid in the presence of a catalyst to


form nitrobenzene. This is an electrophilic substitution reaction.
(i)

Write an equation for the overall reaction.


.....................................................................................................................
(1)

(ii)

State the name of the catalyst used.


.....................................................................................................................
(1)

(iii)

Write the formula, including its charge, of the electrophile involved in


the reaction.
.....................................................................................................................
(1)

(b)

Benzene reacts with chlorine gas in the dark and in the presence of a catalyst
to form chlorobenzene. This is an electrophilic substitution reaction.
(i)

Write an equation for the overall reaction.


.....................................................................................................................
(1)

(ii)

State the name of the catalyst used.


.....................................................................................................................
(1)

(iii)

Write the formula, including its charge, of the electrophile involved in


the reaction.
.....................................................................................................................
(1)

(c)

Benzene reacts with chloroethane in the presence of a catalyst to form


ethylbenzene. This is an electrophilic substitution reaction.
(i)

Write an equation for the overall reaction.


.....................................................................................................................
(1)

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A2 Chemistry Tutorial 1

(ii)

State the name of the catalyst used.


.....................................................................................................................
(1)

(iii)

Write the formula, including its charge, of the electrophile involved in


the reaction.
.....................................................................................................................
(1)

(d)

Benzene reacts with ethanoyl chloride in the presence of a catalyst to form


phenylethanone. This is an electrophilic substitution reaction.
(i)

Write an equation for the overall reaction.


.....................................................................................................................
(1)

(ii)

State the name of the catalyst used.


.....................................................................................................................
(1)

(iii)

Write the formula, including its charge, of the electrophile involved in


the reaction.
.....................................................................................................................
(1)

(e)

Benzene reacts with bromine liquid in the dark and with the presence of a
catalyst to form bromobenzene. This is an electrophilic substitution reaction.
(i)

Write an equation for the overall reaction.


.....................................................................................................................
(1)

(ii)

State the name of the catalyst used.


.....................................................................................................................
(1)

(iii)

Write the formula, including its charge, of the electrophile involved in


the reaction.
............................................................................................................... (1)
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A2 Chemistry Tutorial 1

(f)

Benzene reacts with hydrogen gas to form cyclohexane in the presence of a


catalyst.
(i)

Write an equation for the overall reaction.


.....................................................................................................................
(1)

(ii)

State the name of the catalyst used.


.....................................................................................................................
(1)

(iii)

Name the type of organic reaction that occurs in this reaction.


...............................................................................................................(1)

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A2 Chemistry Tutorial 1

Question 3. Nitration of Benzene

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Nov 2002 Paper 4

A2 Chemistry Tutorial 1

Question 4
Benzene can be converted into chlorobenzene by a chlorination reaction.
(a) State the reagents and conditions necessary to carry out this reaction.
..........................................................................................................................................
......................................................................................................................................[2]
(b) What type of reaction mechanism is this?
......................................................................................................................................[1]
(c) The reaction proceeds via two steps:

Cl

Z+

Y
(i) Draw the structure of the intermediate Y in the box.
(ii) Identify the cation X+..................................................................................................
(iii) Identify the cation Z+..................................................................................................
(iv) Write an equation to show how X+ is produced from the reagents.

...................................................................................................................................[5]

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A2 Chemistry Tutorial 1

Question 5
Benzene can be converted into methylbenzene by a Friedel-Crafts alkylation reaction.
(a) State the reagents and conditions necessary to carry out this reaction.
..........................................................................................................................................
......................................................................................................................................[2]
(b) What type of reaction mechanism is this?
......................................................................................................................................[1]
(c) The reaction proceeds via two steps:

CH3

Z+

Y
(i) Draw the structure of the intermediate Y in the box.
(ii) Identify the cation X+..................................................................................................
(iii) Identify the cation Z+..................................................................................................
(iv) Write an equation to show how X+ is produced from the reagents.

...................................................................................................................................[5]

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A2 Chemistry Tutorial 1

Question 6
Benzene can be converted into phenylethanone by a Friedel-Crafts acylation reaction.
(a) State the reagents and conditions necessary to carry out this reaction.
..........................................................................................................................................
......................................................................................................................................[2]
(b) What type of reaction mechanism is this?
......................................................................................................................................[1]
(c) The reaction proceeds via two steps:

CH3
C

Z+

Y
(i) Draw the structure of the intermediate Y in the box.
(ii) Identify the cation X+..................................................................................................
(iii) Identify the cation Z+..................................................................................................
(iv) Write an equation to show how X+ is produced from the reagents.

...................................................................................................................................[5]

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A2 Chemistry Tutorial 1

Question 7
Reaction I

: Methylbenzene 2-Bromomethylbenzene

Reaction II

: Methylbenzene 2-Chloromethylbenzene

Reaction III

: Methylbenzene 2-Nitromethylbenzene

a) Give the following formula for Methylbenzene:

(i)

Structural formula: .1

(ii)

Molecular formula: 1

(iii)

Empirical formula: 1

b) Methylbenzene is categorized as an aromatic hydrocarbon molecule


(i)
Define the term hydrocarbon molecule.
.1
(ii)

Then explain why methylbenzene is categorised as a aromatic molecule.

.1
c) Name the type of organic reaction that occurred in reaction labeled I, II and III.
.1

d) State the appropriate reagent and condition for reaction labeled as:(i)

:..

(ii)

II

:..

(iii)

III

:..

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A2 Chemistry Tutorial 1

e) Write a balanced equation for reaction labeled as:

f)

(i)

:1

(ii)

II

:1

(iii)

III

:1

Describe the mechanism of reactionI, stating the following clearly:

Labelled active species, show the Movement of electrons, Organic intermediate structure and By-product
5

Methylbenzene

2-Bromomethylbenzene By-product

Active

Organic intermediate

Species

Draw and name one other structural isomers of 2-chloromethylbenzene that is also formed
in the monochlorination reaction of reaction II.
2m
Structural formula

Systematic name

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A2 Chemistry Tutorial 1

Question 8
Reaction I

: Methylbenzene 2-Bromomethylbenzene

Reaction II

: Methylbenzene 2-Chloromethylbenzene

Reaction III

: Methylbenzene 2-Nitromethylbenzene

a) Name the type of organic reaction that occurred in reaction labeled I, II and III.
.1
b) State the appropriate reagent and condition for reaction labeled as:(i)

:..

(ii)

II

:..

(iii)

III

:..

c) Write a balanced equation for reaction labeled as:

(i)

:1

(ii)

II

:1

(iii)

III

:1

d)

Describe the mechanism of reaction III stating the following clearly:Labelled active species,
show the Movement of electrons, Organic intermediate structure and By-product
5

Methylbenzene

Active
Organic intermediate
Species

2-Bromomethylbenzene By-product

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A2 Chemistry Tutorial 1

e) Draw and name one other structural isomer that is produced in reaction I and reaction III.
2m
Reaction
Structural
isomer

III

Systematic
name

Question 9

Molecule U

Reaction 1
Molecule X

Reaction 2

Reaction
3

Molecule W

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A2 Chemistry Tutorial 1

Molecule V

a) Give the systematic name of molecule labeled as:


(i)

Molecule U :1

(ii)

Molecule V :1

(iii)
Molecule W:1
b) Give the molecular formula(not structural formula) for molecule labelled as:
(i)

Molecule U :1

(ii)

Molecule V :1

(iii)

Molecule W:1

(iv)

Molecule X :1

c) State the reagent and conditions for reaction labeled as :


(i)

Reaction 1 :.1

(ii)

Reaction 2:..1

(iii)

Reaction 3:..1

d) Name the type of organic reaction occurred in reaction labelled Reaction 1.


..1

e) Name the type of organic reaction occurred in reaction labelled Reaction 2.


..1

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A2 Chemistry Tutorial 1

Question 10

a) Based on the reaction shown


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

State the reagents and conditions for this change

..1

b) Based on the reaction shown


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

State the reagents and conditions for this change

..1

c) Based on the reaction shown


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

State the reagents and conditions for this change

..1

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A2 Chemistry Tutorial 1


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

State the reagents and conditions for this change

..1

e) Based on the reaction shown


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

State the reagents and conditions for this change

..1

e) Based on the reaction shown


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

State the reagents and conditions for this change

..1

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A2 Chemistry Tutorial 1

f) Based on the reaction shown


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

State the reagents and conditions for this change

..1

g) Based on the reaction shown


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

State the reagents and conditions for this change

..1

h) Based on the reaction shown


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

State the reagents and conditions for this change

..1

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A2 Chemistry Tutorial 1

i) Based on the reaction shown


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

State the reagents and conditions for this change

..1

j) Based on the reaction shown


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

State the reagents and conditions for this change

..1

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A2 Chemistry Tutorial 1