NAME

MARKS

CLASS

UPPER SIX

TOPIC

HYDROCARBONS (ALKENES)

/15

(a) The complete combustion of 0.05 mole of a gaseous

hydrocarbon X yields 0.2 moles of carbon dioxide and
0.2 moles of water.
100 cm3 of X absorbs 100 cm3 of hydrogen gas to
form an alkane, whose relative molecular mass is
58.0.
Determine the empirical and molecular formula of X.
[6 marks]
(b) X has three isomers, P, Q and R. P and Q each reacts
with steam to form the same compound, S, which is
optically active. The oxidation of P and R with
acidified KMnO4 yields a gas which turns limewater
chalky.
Determine the structural formula of P, Q, R and S.
Justify your answer, and write the equations involved.
[9 marks]

ANSWERS:
(a)

Let: hydrocarbon X is CcHh.

CcHh

(c + h4 )

O2

c CO2

h
2

H2O

Given, the mole ratio of CcHh : CO2 : H2O = 0.05 : 0.2 : 0.2
Since each mole of CO2 consists of one mole of carbon atoms,
0.2 mole of CO2 0.2 mole of C atoms
And since each mole of H2O consists of 2 moles of hydrogen atoms,
0.2 mole of H2O (0.2 2) mole of H atoms
Hence, the mole ratio of CcHh : C : H
=

0.05
0.05

=
The mole ratio of C : H

4
4

= 0.05 : 0.2 : 0.4

1
:

0.2
0.05

0.4
0.05

:
:

8
4

(CW)

Therefore, the empirical formula of hydrocarbon X is CH2.

X is an alkene.
X has only one C=C bond because one mol of X undergoes
electrophilic addition with one mol of H2.
The relative molecular mass of X = 58.0 2(1.0) = 56.0
If the molecular formula of X = (CH2)n,
n= 56.0 ( 12.0 + 2(1.0) )
n
= 4 (CW)
Hence, the molecular formula of X = C4H8

(b)

P:
Q:

CH2 CHCH2CH3
CH3CH CHCH3
CH3

R:

CH2

C CH3
OH

CH3CH2CHCH3

S:

P and Q undergoes hydration to form S, which has a chiral carbon.

OH
CH2

CHCH2CH3 + H2O
(P)

H3PO4
330 C, 60 atm

CH3CH2CHCH3
OH

CH3CH

(Q)

CHCH3 + H2O

H3PO4
330 C, 60 atm

CH3CH2CHCH3

P and R undergoes vigorous oxidation, where cleavage of C=C bond

occurred. CO2 gas is released, this means both P and R have terminal
carbon-carbon double bond.
CH2

conc. KMnO4/ H+
CHCH2CH3 + [O]
reflux
(P)

conc. KMnO4/ H+
CH2 C(CH3)2 + [O]
reflux
(R)

CO2 + CH3CH2COOH

CO2 + CH3COCH3