ORGANIC CHEMISTRY (SYNOPTIC) – 3

1. C8H18 represents the formula of saturated hydrocarbons which may exist as several
different structural isomers.
a) Explain what is meant by the term saturated hydrocarbon.
A molecule / compound (
)
which contains only carbon and hydrogen (
)
All the carbon-carbon bonds in the molecule are single bonds (
)
b) Explain what is meant by structural isomers.
Molecules which have the same molecular formula (
)
but different structural formulae (
)
c) Give the names of the structural isomers of C8H18 which have a 5 carbon chain as
the longest chain in the molecule.
2,2,3-trimethylpentane (
) 2,3,3-trimethylpentane (
)
2,2,4-trimethylpentane (
) 2,3,4-trimethylpentane (
)
3-ethyl-2-methylpentane (
) 3-ethyl-3-methylpentane (
)

d) Molecules of C8H18 may be burned as fuels.

i) Write a balanced equation to represent complete combustion of C8H18.
C8H18 + 12½ O2 → 8 CO2 + 9 H2O correct products (
)
correct balancing (
)
ii) Write balanced equation to represent incomplete combustion of C8H18.
C8H18 + 8½ O2 → 8 CO + 9 H2O correct products (
)
OR C8H18 + 4½ O2 → 8C + 9 H2O correct balancing (
)
e) Thermal cracking of C8H18 may lead to the formation of propene as one of the
products. Write an equation to represent thermal cracking of C8H18 which gives
propene as a product.
C8H18 → C3H6 + C5H12
OR C8H18 → 2 C3H6 + C2H6 (
)
f) Propene may be converted into the polymer called polypropene.
i) Write an equation to represent the polymerisation reaction which shows the
structure of both the alkene and the repeat unit in the polymer.
H3C H CH3 H

C C C C
n
H H H H n
correct structures (

)
Correct use of n x 2 (
)
ii) Name the type of polymerisation which is involved in the reaction.
Addition polymerisation (
)

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2. Ethene is the first member of the homologous series of compounds called alkenes.
a) State two general features of a homologous series of compounds.
They may be represented by a general formula
All members contain the same functional group
They show similar chemical properties
They show a gradation in physical properties ANY 2 (

)
b) Bromine or bromine water may be used to test for alkenes. Describe what is seen
when bromine is used in this test.
Changes from orange (
) to colourless (
)
c) Name the mechanism of the reaction which occurs during the test.
Electrophilic addition (
)
d) Show the mechanism of the reaction using curly arrows to show movement of
electron pairs.
H H H H H H

H C C H
H C C H H C+ C H
(
) (
)
Br Br
Br δ+ Br
- Br

(
) structure of ion (
)

Br δ-

e) The product of the reaction may be converted into an alcohol.

i) State a reagent and the conditions used to bring about the conversion.
Aqueous solution (
) KOH / NaOH (
) Heat / reflux (
)
ii) Write a balanced equation to represent the reaction.
CH2BrCH2Br + 2 KOH → CH2(OH)CH2OH + 2 KBr
Correct products (
)
Correct balancing (
)
iii) Name the mechanism of the reaction which occurs.
Nucleophilic substitution (
)
f) The alcohol which has been produced in part (e) may be oxidised by heating under
reflux with acidified potassium dichromate(VI) solution. Show the displayed
structure of the compound which is formed by this oxidation process.

H O C C O H

O O (

)
Total = 37 marks

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