TEST CODE 02212020

FORM TP 2022197 MAY/JUNE 2022

CARIBBEAN E XAM I NAT I O N S COUNCIL

CARIBBEAN ADVANCED PROFICIENCY EXAMINATION®

CHEMISTRY

UNIT 2 – Paper 02

2 hours 30 minutes

READ THE FOLLOWING INSTRUCTIONS CAREFULLY.

1. This paper consists of THREE questions. Answer ALL questions.

2. Write your answers in the spaces provided in this booklet.

3. Do NOT write in the margins.

4. Where appropriate, ALL WORKING MUST BE SHOWN in this booklet.

5. A data booklet is provided.

6. You may use a silent, non-programmable calculator to answer questions.

7. If you need to rewrite any answer and there is not enough space to do so on the
original page, you must use the extra lined page(s) provided at the back of this booklet.
Remember to draw a line through your original answer.

8. If you use the extra page(s) you MUST write the question number clearly in the
box provided at the top of the extra page(s) and, where relevant, include the
question part beside the answer.

DO NOT TURN THIS PAGE UNTIL YOU ARE TOLD TO DO SO.

Copyright © 2021 Caribbean Examinations Council

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Answer ALL questions.

MODULE 1: THE CHEMISTRY OF CARBON COMPOUNDS

1. Figure 1 represents a diagram of a reaction scheme.

Figure 1. Diagram of a reaction scheme

(a) State the reagents and conditions for EACH of the following reactions:

(i) I (from A to B)

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[2 marks]

(ii) II (from A to C)

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[2 marks]

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(iii) Draw the displayed structures and provide names for EACH of the following
compounds:

Compound D

Name ....................................................................................................................
[2 marks]

Compound E

Name ....................................................................................................................
[2 marks]

(b) Consider the equation below which shows the dissociation of chloroethanoic acid in water.

CH2ClCOOH + H2O → CH2ClCOO– + H3O+

(i) Write an expression for the Ka of chloroethanoic acid.

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[2 marks]

(ii) Write an expression to show how pKa is derived from Ka.

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[1 mark]

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(c) Table 1 shows the compounds and pKa values.

TABLE 1: COMPOUND AND pKa VALUES

Compound pKa Value

CH3COOH

CH2ClCOOH

CHCl2COOH

CCl3COOH
[4 marks]

(i) Complete Table 1 above by correctly inserting the pKa value of EACH compound
from the following list of values: 1.48, 0.70, 4.76 and 2.86.

(ii) Give reasons for your assignments in (c) (i).

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[5 marks]

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(d) Account for the fact that the pKb of phenylamine is greater than that of ethylamine.

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[4 marks]

(e) Figure 2 shows the repeating units of two polymers, P and Q.

H H H H O H H O

O O C

CH3 CH3 CH3 CH3 CH3 CH3

Polymer P Polymer Q

Figure 2. Repeating units of two polymers

(i) Draw the structure of the monomer used to form polymer P and name the type of
polymerization involved.

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[2 marks]

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(ii) Draw the structures of the two compounds which react to form the polymer Q and
name the type of polymerization involved.

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[3 marks]

(iii) Identify a compound which in aqueous solution will break down polymer Q but
not polymer P.

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[1 mark]

Total 30 marks

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MODULE 2: ANALYTICAL METHODS AND SEPARATION TECHNIQUES

2. (a) Mass spectrometry is a process by which the atomic mass of atoms or molecules is
determined. Explain how a mass spectrometer works to obtain a mass spectrum of a
molecule.

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[4 marks]

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(b) Figure 3 shows the mass spectrum of a haloalkane.

Figure 3. Mass spectrum of a haloalkane

(i) State the m/z ratio of the M+ and M+2 peak?

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[2 marks]

(ii) Deduce the formula of the fragments at m/z ratio of 43, 107 and 109.

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[3 marks]

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(iii) Determine the formula of the M+ and M+2 molecular ion species and name the
haloalkane.

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[3 marks]

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(c) α-Amino acids are found in human sweat. A student had read that chromatography could
be used to separate and identify the amino acids present in human sweat. The student used
thin layer chromatography (TLC) to separate the α-amino acids in a sample of human
sweat and discovered that three different α-amino acids were present.

(i) Name the process by which TLC separates α-amino acids.

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[1 mark]

(ii) The chromatogram was treated to show the positions of the separated α-amino
acids. Explain how the student could analyse the chromatogram to identify the
three α-amino acids that were present.

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[2 marks]

(iii) Several α-amino acids have structures that are very similar. Suggest why this could
cause problems when using TLC to analyse mixtures of α-amino acids.

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[2 marks]

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(d) At the end of an organic reaction, a TLC of the reaction mixture indicates the presence of
unreacted starting material benzoic acid as well as the impurity 1,4-dimethoxybenzene.

(i) Outline a series of steps indicating how this mixture can be separated, and the two
components recovered, by the process of solvent extraction.

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[5 marks]

(ii) State what is meant by the term ‘partition coefficient’.

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[1 mark]

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(iii) If iodine is shaken with 100 cm3 of water and 100 cm3 of an organic solvent, the
concentration of iodine in the water layer is 4.0 × 10–3 mol dm–3 and in the organic
solvent is 1.0 × 10–2 mol dm–3.

Calculate the partition coefficient for iodine between the organic solvent and water.

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[2 marks]

(iv) The aqueous layer is separated and shaken with 50 cm3 of the pure organic solvent.
Determine the concentration of iodine in the organic solvent at equilibrium in mol
dm–3? Show ALL working.

[5 marks]

Total 30 marks

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MODULE 3: INDUSTRY AND THE ENVIRONMENT

3. (a) Crude oil, a complex mixture of naturally occurring hydrocarbons, is a raw material that
has many uses. The crude oil must be separated into its various components and modified
to be useful.

TABLE 2: CRUDE OIL FRACTIONS AND THEIR USES

Boiling Number of
Fraction Uses
Range (°C) Carbon Atoms

Refinery gases Heating, cooking

80–180 5–10

16–25

Residue ➢ 350° Asphalt/bitumen

Table 2 shows crude oil fractions and their uses. Complete Table 2 by inserting the missing
information in the blank spaces. [4 marks]

(b) (i) Define the term ‘catalytic cracking’.

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[2 marks]

(ii) Write a balanced equation to show the products of the cracking of decane, C10H22.

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[2 marks]

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(iii) Explain the principles involved in the fractional distillation of crude oil.

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[3 marks]

(iv) Explain how ONE adverse effect of the petroleum industry can impact the
environment.

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[3 marks]

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(c) (i) Define EACH of the following terms.

Reuse

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Recycle

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Reduce

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[3 marks]

(ii) Discuss how the concepts of reuse, recycle and reduce can be applied practically
to glass waste.

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[3 marks]

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(d) Describe the chemical processes involved in the production of chlorine and sodium
hydroxide when the diaphragm cell is used. Your answer must include the types of
reaction taking place and the equations representing the chemical reactions.

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[5 marks]

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(e) The chlorine produced in the chlor-alkali industry may be reacted with the other products of
the electrolysis, hydrogen and sodium hydroxide to produce two useful products. Describe

(i) the chemical changes which occur to produce hydrochloric acid

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[2 marks]

(ii) the chemical changes which occur to produce sodium hypochlorite (bleach)

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[1 mark]

(iii) TWO modifications that could be made to the structure of the electrolytic cell to
ensure that these chemical changes in (e) (ii) do not occur.

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[2 marks]

Total 30 marks

END OF TEST

IF YOU FINISH BEFORE TIME IS CALLED, CHECK YOUR WORK ON THIS TEST.

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