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Chem a2 Tutorial 1 Benzene and Its Derivatives

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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

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