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organic chemistry benzene and its derivatives. chemistry organic reaction tutorial for a-level chemistry especially cie a2 level chem.
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Page 1 A2 Chemistry Tutorial 1
Chemistry A2 Tutorial 1: Benzene and its derivatives
Question 1. Complete the table below with the correct formula
Name and Molecular formula
Structural formula Skeletal formula Empirical Formula
Benzene C6H6
Methylbenzene
Ethylbenzene
Nitrobenzene
1,3-dinitrobenzene
Cyclohexane
Cyclohexene
Page 2 A2 Chemistry Tutorial 1
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)
Page 3 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)
Page 4 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)
Page 5 A2 Chemistry Tutorial 1
Question 3. Nitration of Benzene Nov 2002 Paper 4
Page 6 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:
+
Y
+ Z +
(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]
Cl
Page 7 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:
+
Y
+ Z +
(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]
CH3
Page 8 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:
+
Y
+ Z +
(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]
C
O CH3
Page 9 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) I :……………………………………………………………………..
(ii) II :……………………………………………………………………..
(iii) III :……………………………………………………………………..
Page 10 A2 Chemistry Tutorial 1
e) Write a balanced equation for reaction labeled as:
(i) I :……………………………………………………………………………………………………………………1
(ii) II :……………………………………………………………………………………………………………………1
(iii) III :……………………………………………………………………………………………………………………1
f) 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 Active
Species
Organic intermediate
2-Bromomethylbenzene By-product
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
Page 11 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) I :……………………………………………………………………..
(ii) II :……………………………………………………………………..
(iii) III :……………………………………………………………………..
c) Write a balanced equation for reaction labeled as:
(i) 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
Species
Organic intermediate
+
2-Bromomethylbenzene By-product
Page 12 A2 Chemistry Tutorial 1
e) Draw and name one other structural isomer that is produced in reaction I and reaction III.
2m
Reaction I III
Structural isomer
Systematic name
Question 9
Molecule U
Reaction 1
Molecule X
Reaction 2
Molecule V
Reaction
3
Molecule W
Page 13 A2 Chemistry Tutorial 1
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
Page 14 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
Page 15 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
Page 16 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
Page 17 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