Topic 14 Hydrocarbons_CW

TOPIC 14: HYDROCARBONS
1. The complete combustion of 2 moles of a straight chain alkane produces 400 dm 3 of carbon
dioxide measured at 301 K and 1 × 105 Pa. Carbon dioxide can be assumed to behave as an ideal
gas under these conditions. What is the formula of the straight chain alkane?
A C8H18 B C16H34 C C20H42 D C40H82
2. There are three structural isomers with the formula C5H12. Which formulae correctly represent
these three structural isomers?
A CH3CH2CH2CH2CH3 CH3CH(CH3)CH2CH3 C(CH3)4
B CH3CH2CH2CH2CH3 CH3CH(CH3)CH2CH3 CH3CH2CH(CH3)CH3
3. When heated with chlorine, the hydrocarbon 2,2-dimethylbutane undergoes free radical
substitution. In a propagation step a free radical X• is formed. How many different structures of
X• are possible?
A2 B3 C4 D5
4. Complete combustion of a sample of a hydrocarbon gave 0.132 g of carbon dioxide and

0.054 g of water. Which formulae could correctly represent this hydrocarbon?
1 CH2=CH2 2 CH3CH=CH2 3 CH3CH=CHCH3
A 1, 2 and 3 B 1 and 2 only C 1 and 3 only D 1 only
5. Propene undergoes a variety of reactions. Which row is correct?

reagent added to propene products include
A Br2(aq) 1-bromopropane
B cold, dilute, acidified KMnO4(aq) propanoic acid
C HBr(g) 2-bromopropane
D hot, concentrated, acidified KMnO4(aq) propanoic acid
6. The diagram shows the structure of 1,3-butadiene.
The addition reaction between 1,3-butadiene and two molecules of hydrogen bromide can
produce three structurally isomeric products. How many of these products have at least one
chiral centre?
A0 B1 C2 D3
7. Limonene is found in lemon and orange oils.
What will be the major product when limonene is reacted with an excess of dry hydrogen chloride?
8. 2-methylpropene can react in more than one way with chlorine. One of the reactions follows
the pathway shown.
Which statements about this mechanism are correct?

1 The intermediate has all carbon atoms in the same plane.
2 There is an electrophilic attack on the double bond.
3 It is a free radical mechanism
9. Which compounds would produce a carboxylic acid and a ketone when treated with
hot, concentrated, acidified KMnO4?
10. A species of termite produces a chemical defence secretion which contains the molecule
shown.
To help determine the structure of this compound, it is treated with hot, concentrated, acidified
manganate(VII) ions. Which compounds are produced in this reaction?
1 CO2 2 CH3COCH3 3 CH3CO2H
11. Compound X can be converted into compound Y in a single step.
What could be the identity of X?

12. This question is about molecules with molecular formula C4H8.
(a) Give the structures of a pair of positional isomers with the formula C 4H8.
C-C-C=C C-C=C-C
CH2 = CH2CH2CH3 CH3CH=CHCH3
(b) Give the structures of a pair of chain isomers with the formula C4H8, that do not exhibit
stereoisomerism.
C
l
C-C-C=C C-C=C
CH2=CHCH2CH3 (CH3)2C = CH2
(c) Give the structures and full names of a pair of stereoisomers with the formula C 4H8.
CH3 CH3 H CH3

l l l l
C=C C=C
l l l l
H H CH3 H
cis - but-2-ene trans - but-2-ene
(d) The structure of a molecule, A, of formula C4H8 is shown. Draw a functional group isomer
of molecule A in box B. Explain how molecules A and B could be distinguished by a chemical
test. Add bromine water. Solution turns from brown to colourless with B
No reaction with A
CH2 = CHCH2CH3
13. Consider the hydrocarbon X with the structural formula (CH 3)2C=CH2.
(a) Name X.
2-methylprop-1-ene
……………………………………………………………………………………………………
(b) Complete the mechanism for the reaction of this compound with hydrogen bromide.
Include all necessary curly arrows, lone pairs, charges and partial charges.
(c) Explain fully why 2-bromomethylpropane is the major product of this reaction while only
relatively small amounts of 1-bromomethylpropane are produced.
According to Markovnikov rule, carbon in 2-bromomethylpropane is bonded to 3 alkyl groups.

Inductive effect is shared across 3 alkyl group, so tertiary carbocation is the most stable.
Carbon in 1-bromomethylpropane is bonded to only 1 alkyl group.
14. Consider the hydrocarbon Y with the structural formula (CH3)2C=C(CH3)2

(a) Name Y.
2,3 - dimethylbut-2-ene
……………………………………………………………………………………………………
(b) Draw the skeletal formula of the organic product of the reaction of this compound with cold,
dilute, acidified manganate(VII) ions.
(c) Draw the skeletal formula of the organic product of the reaction of this compound with hot,
concentrated, acidified manganate(VII) ions.
(d) Draw the structure of part of a molecule of the addition polymer formed from this compound,
showing exactly three repeat units.

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TOPIC 14: HYDROCARBONS

4. Complete combustion of a sample of a hydrocarbon gave 0.132 g of carbon dioxide and

5. Propene undergoes a variety of reactions. Which row is correct?

7. Limonene is found in lemon and orange oils.

Which statements about this mechanism are correct?

A 1, 2 and 3 B 1 and 2 only C 1 and 3 only D 1 only

11. Compound X can be converted into compound Y in a single step.

What could be the identity of X?

CH2 = CH2CH2CH3 CH3CH=CHCH3

CH3 CH3 H CH3

cis - but-2-ene trans - but-2-ene

According to Markovnikov rule, carbon in 2-bromomethylpropane is bonded to 3 alkyl groups.

14. Consider the hydrocarbon Y with the structural formula (CH3)2C=C(CH3)2

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