AS LEVEL CHEMISTRY

TOPIC 7 – INTRODUCTION TO ORGANIC

CHEMISTRY
TEST
Answer all questions

Max 50 marks

Name ……………………………………………………………..

Mark ……../50 ……....% Grade ………

1. (a) (i) Name the process used to separate petroleum into fractions.

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(ii) Give the molecular formula for an alkane with nine carbon atoms.

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(iii) Write an equation for the complete combustion of the alkane C11H24

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(iv) Write an equation for the incomplete combustion of C11H24 to produce carbon and water
only.

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(4)

(b) Alkenes can be produced by cracking the naphtha fraction obtained from petroleum.

(i) Write an equation for the thermal cracking of one molecule of C10 H22 to give
one molecule of propene and one molecule of an alkane only.

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(ii) Draw the structure of the chain isomer of but-1-ene.

(2)

(c) The alkanes and the alkenes are examples of homologous series of compounds.
One feature of an homologous series is the gradual change in physical properties
as the relative molecular mass increases. State two other general features of an
homologous series of compounds.

Feature 1 ......................................................................................................

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Feature 2 ......................................................................................................

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(2)
(Total 8 marks)
2. Q and R have the molecular formula C6H12

Both are branched-chain molecules and none is cyclic.

Q can represent a pair of geometrical isomers.
R can represent another pair of geometrical isomers different from Q.

Draw one possible structure for one of the isomers of each of Q and R.

Structure of Q

Structure of R

(Total 2 marks)

3. Four isomers with the formula C4H9OH are given below:

Isomer Name

CH3CH2CH2CH2OH butan-1-ol

2-methylpropan-2-ol

(i) Complete the naming of the isomers in the table above.

(ii) Name the type of isomerism shown by these four isomers.

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(Total 3 marks)
4. Draw and name the geometrical E-Z isomers of pent-2-ene.

Isomer 1 Isomer 2

Name ............................….................... Name .............…...........................

(Total 2 marks)

5. Octane is the eighth member of the alkane homologous series.

(a) State two characteristics of a homologous series.

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(2)

(b) Name a process used to separate octane from a mixture containing several different alkanes.

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(1)
(c) The structure shown below is one of several structural isomers of octane.

Give the meaning of the term structural isomerism.

Name this isomer and state its empirical formula.

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(4)

(d) Suggest why the branched chain isomer shown above has a lower boiling point than octane.

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(2)
(Total 9 marks)
6. (a) The structure of the bromoalkane Z is

Give the IUPAC name for Z.

Give the general formula of the homologous series of straight-chain bromoalkanes that
contains one bromine atom per molecule.

Suggest one reason why 1-bromohexane has a higher boiling point than Z.

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(3)

(b) Draw the displayed formula of 1,2-dichloro-2-methylpropane.

State its empirical formula.

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(2)
(Total 5 marks)
7. (a) The hydrocarbon but-1-ene (C4H8) is a member of the homologous series of alkenes.
But-1-ene has structural isomers.

(i) State the meaning of the term structural isomers.

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(2)

(ii) Give the IUPAC name of the position isomer of but-1-ene.

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(1)

(iii) Give the IUPAC name of the chain isomer of but-1-ene.

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(1)

(iv) Draw the displayed formula of a functional group isomer of but-1-ene.

(1)

(b) But-1-ene burns in a limited supply of air to produce a solid and water only.

(i) Write an equation for this reaction.

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(1)

(ii) State one hazard associated with the solid product in part (b)(i).

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(1)

(c) One mole of compound Y is cracked to produce two moles of ethene, one mole of but-1-ene
and one mole of octane (C8H18) only.

(i) Deduce the molecular formula of Y.

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(1)

(ii) Other than cracking, give one common use of Y.

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(1)
 (d) In cars fitted with catalytic converters, unburned octane reacts with nitrogen monoxide to
form carbon dioxide, water and nitrogen only.

(i) Write an equation for this reaction.

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(1)

(ii) Identify a catalyst used in a catalytic converter.

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(1)
(Total 11 marks)

8. Two stereoisomers of but-2-ene are formed when 2-bromobutane reacts with ethanolic
potassium hydroxide.

(i) Explain what is meant by the term stereoisomers.

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(ii) Draw the structures and give the names of the two stereoisomers of
but-2-ene.

Stereoisomer 1 Stereoisomer 2

Name ................................................. Name ................................................

(iii) Name this type of stereoisomerism.

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(5)
(Total 5 marks)
9. The number of structural isomers of molecular formula C4H9Br is

A 5

B 4

C 3

D 2
(Total 1 mark)

10. An alkane contains 30 hydrogen atoms per molecule. Its empirical formula is

A C6H15

B C7H15

C C14H30

D C15H30
(Total 1 mark)

11. The correct systematic name for is

A 2-ethyl-3,4-dimethylpent-2-ene

B 4-ethyl-2,3-dimethylpent-3-ene

C 2,3,4-trirnethylhex-3-ene

D 3,4,5-trimethylhex-3-ene
(Total 1 mark)
12.

Which one of the following is not a structural isomer of Compound M?

D
(Total 1 mark)

13. The number of structural isomers of C3H2Cl6 is

A 2

B 3

C 4

D 5
(Total 1 mark)
 Topic 8 EXERCISE 3 – reactions of haloalkanes

1. a) Draw the structure of a chlorofluorocarbon and write an equation to show

how it can release chlorine radicals in the presence of ultra-violet light.

b) Write equations to show how chlorine radicals can catalyse the destruction
of ozone.

2. a) Explain why haloalkanes can react with nucleophiles.

b) Write an equation and give the mechanism for the following reactions:

i) bromoethane with aqueous sodium hydroxide

ii) 2-chloropropane with potassium cyanide
iii) 1-iodobutane with ammonia

3. State two types of reaction that could take place when 1-chlorobutane reacts with
potassium hydroxide. Give the mechanism for each reaction and state the role of
the hydroxide ion in each case. Suggest conditions which would favour each type
of reaction.

4. Suggest, giving reasons, which of chloroethane, bromoethane and iodoethane will

react fastest with sodium hydroxide.

5. State the possible products that could be formed when the following haloalkanes
undergo elimination. If more than one product is formed, identify them both and
explain how each is formed.

a) 1-bromobutane
b) 2-bromobutane
c) 1-bromomethylpropane
d) 2-bromomethylpropane
 Topic 8 EXERCISE 2 – addition reactions of alkenes

1. Write equations, using displayed formulae, to show the conversion of but-1-ene

into:

a) polybut-1-ene
b) butan-2-ol
c) 2-bromobutane
d) 1,2-dibromobutane

2. a) Explain why alkenes tend to react with electrophiles.

b) Show the mechanisms for the following reactions:

i) ethene with bromine

ii) but-2-ene with hydrogen bromide
iii) ethene with concentrated sulphuric acid

c) Explain how bromine can behave as an electrophile.

3. The following reactions give two products in unequal amounts. In each case,
identify the two products, state which is the major product, explain why it is the
major product and give the mechanism for its formation.

a) but-1-ene with HBr

b) methylpropene with concentrated sulphuric acid
 TOPIC 8 EXERCISE 4 – Alcohols

1. Write equations to show the production of ethanol by

i) fermentation of glucose
ii) hydration of ethene

Give the conditions needed for each process and state the relative advantages and
disadvantages of each process.

2. Identify the organic product or products formed by the dehydration of

a) ethanol
b) butan-1-ol
c) butan-2-ol
d) dimethylpropan-1-ol

3. Give the names and structures of all eight alcohols with the formula C5H12O. State
in each case whether they are primary, secondary or tertiary alcohols.

a) Identify the three isomers which can give two different alkenes when
dehydrated and identify the possible alkene products in each case.

b) Identify the seven alcohols which can undergo mild oxidation and identify
the oxidation products in each case.

c) Of these oxidation products, four can undergo further oxidation. Identify

these four aldehydes and identify the further oxidation product in each
case.

4. Using structural formulae, write equations for the following processes:

a) mild oxidation of propan-1-ol

b) oxidation of butanal
c) oxidation of propan-2-ol
 TOPIC 8 EXERCISE 1 – CHLORINATION OF ALKANES

1. Alkanes react with halogens in a reaction described as homolytic free radical

substitution. Explain what is meant by the terms:
i) homolytic
ii) free radical
iii) substitution

2. a) Using full displayed formulae, show the four steps involved in the
reaction of ethane with chlorine to give chloroethane. State the type of
reaction involved in each step.

b) Show by mans of additional steps how this mechanism can account for
the formation of:
iv) 1,1-dichloroethane
v) butane