2018 JC1 H2 Chemistry

Promo Revision – Organic Chemistry WS 1

Topics: Isomerism, Alkanes, Alkenes, Gaseous State and Kinetics
Total: 27 Marks Duration: 40 Min
Gaseous State

1 (a) A gaseous sample of 0.20 g of an alkane took up a volume of 87 cm3 at a temperature

of 380 K and a pressure of 1.01 x 105 Pa. Use these data to calculate the Mr of the
alkane and hence suggest its molecular formula. [2]

PV = nRT
1.01 x 105 x 87 x 10-6 = 0.20/ Mr x 8.31 x 380
 Mr = 71.9
 Therefore the alkane is C5H12.

(b) Oxygen and carbon dioxide gas are real gases and exhibit deviation from ideal gas.
Explain which gas exhibit greater deviation at

(i) low temperatures and [1]

 CO2 contains a greater total number of electrons than O2 molecule and

hence has a larger electron cloud. Hence there exist stronger and more
extensive instantaneous dipole – induced dipole interactions between the
molecules of CO2. So, CO2 showed greater negative deviation than O2.Thus
Preal<Pideal and PV  1 . Hence there is a negative deviation.
nRT

(ii) high pressures [1]

 CO2 has a larger molecular size than O2, the volume taken up by CO2 gas
molecules is greater. So, CO2 should show a greater positive deviation than
O2. Vreal>Videal and PV  1 . Hence there is a positive deviation.
nRT

[Total: 4]

Alkanes, Isomerism and Kinetics

2 Three isomers of C6H10 are shown below.

A B C
(a) State the specific form of constitutional isomerism exhibited by A, B and C. [1]
Positional isomerism

1
(b) Apart from exhibiting constitutional isomerism, A can exhibit stereoisomerism.
Draw the two stereoisomers of A and state their relationship. [3]

Relationship: Enantiomers
(c) A can be converted to compounds D and E as shown.
Write in the box below, the reagents and conditions needed to convert D to E. [1]

H2, Ni Cl2(g)

heat UV or heat

A D E
(d) A sample of compound E was dissolved in dilute aqueous ethanol and reacted with
sodium hydroxide. Several experiments were conducted at constant temperature and
the initial rate of reaction was determined in each experiment.

experiment [E] / mol dm–3 [NaOH] / mol dm–3 rate / mol dm–3 s–1

1 0.0200 0.0100 3.00 x 10–4

2 0.0200 0.0200 3.00 x 10–4

3 0.0400 0.0300 6.00 x 10–4

Calculate
(i) Calculate the rate constant, stating its unit. [2]
Using expt 1,

rate 3.00 x 10−4

k=
[E]
= = 0.0150 s–1
0.020

(ii) Hence, calculate the time taken for the concentration of E to be halved. [1]
ln2 ln2
t1/2 = k
= 0.0150 = 46.2 s

2
(e) State and outline the mechanism to convert compound D to E in part (c). [4]
Name of mechanism: Free radical substitution

[Total: 12]

2017 ACJC Promo Section B Structured

3
Alkenes and Isomerism
3 Compound A undergoes a series of reactions as shown in the flow-chart below:

(a) (i) Compound A exhibits stereoisomerism. Draw all the stereoisomers. [2]

●●

and

(ii) State the reagents and conditions for Reaction I. [1]

● Reaction I: Acidic KMnO4, heat

(iii) Draw the structure of Compound B and C. [2]

● Compound C:

● Compound B:

4
(ii) Name and describe the mechanism of the reaction to form the major product,
Compound B from Compound A, [3]

 Name: Electrophilic addition

 Step 1

 Step 2

fast

Compound B

(iii) Devise a three-step syntheses, starting with but-1-ene to ethanoic acid.

Identify the reagents at each step, and draw the structural formulae of the
intermediates. [3]

1 step and 1 intermediate = 1 mark

[Total: 11]