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qb, rESrcoDE 02212020

FORM TP 20111s6 MAY/JUNE2OIT

CARIBBEAN EXAMINATIONS COUNCIL

ADVAI\CED PROFICIENCY EXAMINATION
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-l CHEMISTRY
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2hours30minutes
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READ THE F'OLLOWN.IG INSTRUCTIONS CAREFULLY.

l. This paper consists of sIX compulsory questions in TWo sections.

2. Section A consists of THREE structured questions, one from each Module.

I Section B consists of THREE extended response questions, one from each
Module.

3. For SectionA, write your answers in the spaces provided in this booklet. For
Section B, write your answers in the answer booklet provided.

4. All working must be shown.

5. The use of silent non-programmable calculators is permitted.

6. A data booklet is provided.

Copyright @ 2009 Caribbean Examinations Council.

All rights reserved.
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SECTION A

AnswerALL questions in this section.

Write your answers in the spaces provided in this booklet.

MODULE 1

'':':- ' ': ''i.:: 4 THE cHEMrsrRy oF cARBoN coMpouNDs

)liAiiilir (r,-
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(a) Complete fabte t by indicating simple test tube reactions used to distinguish between the
pgi{g_g!-gpounds indicated. Record your expected observations in the spaces provided.
..,r1'1.1.1
TABLE 1: TEST TUBE REACTIONS FOR DISTINGTIISHING PAIRS OF CARBON COMPOT'I\DS

Co-po!o9!_ Test Observation

(i)H H HHH
^\ | lll CompoundA
C: C-CH, and H-C-C-C-H Addition of Brr(ag) to both decolourized Brr(ag);
/lll
H HHH Aand B colour changes from
brown to colourless

AB
(ii)
H
I

H-C-H
HH HIH
tl lrl
H-C-C-H and H-C-C-C-H
ll lll
HOH H OHH
A B

(iii)
o HHO
ll llll Addition of Tollen's reagent
H.C-C-CH..'and H-C-C-C-H
' ll to bothA and B
HH
A B
(iv)
CH, o
I tl
HrC-C-CH3 HrC-C-CH3
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OH

A
5 marksl

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(b) The structural formula ofA (2-bromo-2-methylpropane) is given below.

cHt
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HrC-C-CH3
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Br

I (i)
A

Show the steps involved in the mechanism ofthe reaction betweenAand sodium
hydroxide. Use curved arrows and fish hook notation to show the movement of
electrons.

[ 4 marksl
(iD state the name of the reaction mechanism outlined in (b) (i) above.

I lmark]

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(c) The reaction scheme below shows the conversion of Compound X to Compound Y in j

three steps.

HHHHH
lllstentll/H
H- c- c -c-oH+H-c -c: c
lll l\11 i

HHHH
xl SteP 2
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v
HOHHHH
I ll I steor I | |

H-C-C-C-H *+H-C-c-c-H
lllll HOHH
H H
Y

(D State the reagent(s) used for the conversion at EACH step'

Step 1

Step 2

Step 3
[ 4 marksl

(ii) Name the process which occurs in Step 3 of the reaction.

I l mark]
Total 15 marks

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MODULE 2
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I AI\ALYTICAL METHODS AND SEPARATION TE CHNIQ UES

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2. (a) Distinguish between the terms 'precision' and 'accuracy'.
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[ 3 marks]
(b) A student was asked to measure 50 cm3 of a liquid in order to carry out an experiment.

List THREE pieces of apparatus that could be used to accurately measure the required
volume.

[ 2 marksl
(c) Each of four students carried out an experiment to determine the percentage of acetic
acid in a vinegar sample. The procedure was repeated four times by each student and
the results recorded in Table 2.

(D Complete Table 2 by calculating the standard deviation (SD) of EACH of the

four sets of results, using the formula

SD:

TABLE 2: RESULTS OF EXPERIMENT

Student
Volume I Volume 2 Volume 3 Volume 4
(cmt) (cmt) (cm') (cm')
Mean,f (cm3) SD

I 24.t5 24.20 24.10 24.05 24.t3

2 26.00 24.00 24.00 26.00 25.00
a
J 29.r5 24.95 33.25 27.75 28.78
4 25.t0 24.90 25.00 25.00 25.00

[ 2 marks]

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(iD Evaluate the results obtained by EACH student by commenting on the accuracy
and precision of EACH set of titre volumes.

Student l:
Student2:

Student 3:

Student 4:
[ 4 marksl
(d) A student was asked to calibrate a l0 cm3 pipette. Outline the experimental steps that
should be taken by the student to complete this exercise.

[ 4 marksl
Total 15 marks

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MODULE 3

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INDUSTRY AI\D THE ENVIRONMENT
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3. (a) Outline the THREE principles of the primary distillation of crude oil.

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I (b) To meet the requirements of modern industry, secondary refining processes such as
'cracking' and'reforming' are used.

Define the terms:

O Cracking

(ii) Reforming

[ 2 marksl
(c) Octane undergoes cracking to produce two hydrocarbons, one of which is
burane.
I

.J write the balanced equation which represents this process.

[ 2 marksl
(d) The products of cracking are widely used as raw materials in the manufacture
of
petrochemicals.

State THREE uses of these products.

[ 3 marksl

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(e) Figure I shows the materials used to illustrate the process of fermentation.

Ca(OH), (aq)

Figure 1. Fermentation Process

(i) State the names of the substances A and B in the suspension'

A.

B.
[ 2 marksl
(ii) State what would be observed after aperiod of time in the

conical flask

beaker.

[ 2 marks]
(iiD The fermentation process is carried out in surroundings where the temperature
for this
is controlled. very high temperatures must be avoided. Give a reason
condition.

[1 mark l
Total 15 marks

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SECTION B

Answer ALL questions in this section.

Write your answers in the separate answer booklet provided.

MODULE 1

THE CHEMISTRY OF CARBON COMPOT'NDS

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4. (a) (i) Define the term 'structural isomerism'. I 2 marksl
(iD Identifu Two types of structural isomers, giving an example of EACH.
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(b) l0 cm3 of a gaseous hydrocarbon were mixed with 45 cm3 of oxygen and exploded in
a reaction chamber- After cooling to room temperature, the residual gases tccupied
30 cm3. By absorption with NaOH solution, a decrease in volume of20 cmlwas
produced.
The remaining gas was shown to be oxygen. Determine the molecular formuta
of the
hydrocarbon. (Pressure remained constant at I atm.)
[
4 marks]

(c) Explain the difference in acidity of alcohols, phenols and carboxylic acids. In your
response' make reference to acid strength, inductive and conjugative effects.

[ 5 marksl
Total 15 marks

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MODULE 2
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ANALYTICAL METHODS AI\D SEPARATION TE CHNIQUES

f,. (a) (i) State the source of absorption in UVA/IS spectroscopy. I l mark]
(iD Use an energy level diagram to show the electronic transitions that can occur in
UV/US spectroscopy. [ 3 marks]
(b) (i) Define the term'chromoPhore'. I lmarkl
Naphthalene, P, the formula for which is given below, is a constituent of coal
tar, a crude oil residue.

(ii) Suggest the chromophore in P that is responsible for the absorption of UV

radiation. I l mark]
volume of
A sample of coal tar was subjected to solvent extraction using ethanol' The
extraci was reduced and a solution of P was obtained by separation techniques'

A sample of the solution incell of path I cm gave an absorbance of 1 .2 at a wavelength

a
of 3l2nm and an extinction coefficient (molar absorptivity) of 288 dm3 mol-r cm-r'

(iii) Calculate the concentration of P in the solution' [ 3 marks]

Explain the use of calibration curves and standard solutions in UVA/IS

analysis'
(c)
[ 4 marks]
(d) List TWO uses of IIV/VIS spectroscopy in chemical analysis. [ 2 marks]
Total 15 marks

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MODULE 3

INDUSTRY AND ENVIRONMENT

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I 6. Figure 2 presents a simplified version of the nitrogen cycle with some components, A, B, C and
D, unlabelled.

in the soil

Figure 2. The nitrogen cycle

(a) Identifr the unlabelled components, A, B, C and D, in Figure 2. [ 4 marksl

(b) The nitrogen and carbon cycles have natural sources which enable the maintenance of
balance. However, the input of additional gases due to human activity has led to the
disturbance of the existing balance.

State TwO human activities that have led to the disturbance of the balance of these
cycles.
[ 2 marks]
(c) Explain, with the use ofrelevant equations, the processes which allow for the maintenance
of the concentration of ozone in the stratosphere.
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In your answet discuss the process of oxygen formation and decomposition.
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Total 15 marks
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END OF TEST
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