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TEST CODE

FORM TP 23182

002671

MAY/JUNE 2003

CARIBBEAN EXAMINATIONS COUNCIL

ADVANCED PROFICIENCY EXAMINATION


CHEMISTRY
UNIT 1 - PAPER 01
1 hour 45 minutes

Candidates are advised to use the first 15 minutes for reading


through this paper carefully.

READ THE FOLLOWING INSTRUCTIONS CAREFULLY

1. This paper consists of NINE questions.


2. There are THREE questions from each Module. Answer ALL questions.
3. Write answers in this booklet.
4. ALL working must be shown in this booklet.
5. The use of non-programmable calculators is permitted.
6. A Data Booklet is provided.

Copyright 2002 Caribbean Examinations Council.


All rights reserved.
002671/CAPE/F 2003

MODULE I
Answer ALL questions.

38
1. Ina decay series, 29 2 U decays by a-emission to give an isotope of element X, which then decays
by (3-emission to give element Y.
(a) Complete the equation for EACH of the decay processes described, by including the mass
and proton numbers for X and Y.
238
(i) 92 U

X + a +

Y + P
[ 2 marks]
(b) Complete the diagram in Figure1 to show how a - particles, (3- particles and y-rays would
be deflected by passage through an electric field, taking care to consider BOTH direction
and degree of deflection of EACH.

E)

Particle
source

Figure 1
[ 4 marks]

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-3

(c) The graph in Figure 2 represents a plot of number of neutrons on the vertical axis and the
number of protons for isotopes of the elements on the horizontal axis. Stable nuclei fall
within the `band of stability' in which the n/p ratio ranges from 1 for light nuclei to 1.5 for
heavier nuclei. Radioactive decay leads to the formation of a more stable nucleus.

n/p ratio = 1

24

43 K
19

19 Proton number

Figure 2
Suggest the type of decay that would occur for 19 K based on its position as shown in
the diagram. Explain your reasoning.

[ 4 marks]
Total 10 marks

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002671/CAPE/F 2003

2. (a) Name and describe the nature of the MAIN intermolecular forces between the following
molecules:
(i) NH3

(ii) CO2

[ 6 marks]

(b) Ammonia forms an addition compound with covalent beryllium chloride, BeCI2.
(i) Suggest the formula of the compound formed.

[ 1 mark ]
(ii) Draw a dot-cross diagram to show the electron distribution in the addition
compound.

[ 2 marks]
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(iii) Draw a diagram to illustrate the shape of the addition compound.

[ 1mark]
Total 10 marks

3. (a) Explain the following terms:


(i) Bond energy

[ 2 marks]
(ii) Enthalpy change of combustion, AH$

[ 2 marks]

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00267 1 /CAPE/F 2003

-6

(b) DMSO, dimethylsulphoxide, is an organic liquid having the molecular structure shown
below.
H O H
1 11 1
H-C-S-C-H
H

It is an excellent solvent and is known to penetrate the skin very readily. DMSO has the
potential for use as a drug in the treatment of arthritic pain.
Suggest ONE reason for the ability of DMSO to penetrate the skin.

[ 1 mark ]
(c) (i) Write an equation for the combustion of DMSO.

[ 2 marks]

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002671/CAPE/F 2003

-7-

(ii) Use the bond energy data in Table 1 to calculate AH of DMSO.

TABLE I: BOND ENERGY DATA


Bond

Energy / KJ mol-1

C-H
C-S
S=0
0=0
0-H
C=O

415
270
523
498
464
745

[ 2 marks]

(d) Comment on the suitability of DMSO for use as a fuel.

[ 1 mark]
Total 10 marks

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002671 /CAPE/F 2003

MODULE 2
Answer ALL questions

4. Table 2 below shows the functional group analysis of the compounds, A, B, C and D.

TABLE 2 : FUNCTIONAL GROUP ANALYSIS OF COMPOUNDS A - D


Compound

Test

Observation

Brz in

decolourisation

Structural Formula
of Functional Group

1,1,1, trichloro-

ethane

PCl 5
I 2 / NaOH

dense white
fumes
yellow ppt.

litmus test
PCl 5

blue -) red
dense white
fumes

litmus test
Br2 (aq)

blue---) red
white ppt.

(a) Complete Table 2 by writing the structural formulae for EACH compound based on the
observations given .
[
4
marks]
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002671/CAPE/F 2003

(b) Compound B is a fragrant liquid which when heated with excess concentrated H,,SO4
produces a gas, G, which decolourises bromine. When G reacts with HBr, two isomeric
compounds, E and F, with relative molecular mass of 123 are obtained.
Write the displayed formula for EACH of the following:

(i) E

[ 1 mark]

[ 1 mark ]

[ 1 mark ]

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(iv) G

[ 1 mark]
(v) -The ionic intermediates formed in the production of:
a)

[ l mark ]

b)

[ l mark]

Total 10 marks

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002671/CAPE/F 2003

- 11 -

5. (a) State the type of reaction mechanisms involved in the following conversions:
(i)

C2H6

> CH3 CH7 Cl

(ii) C3H7C1

(iii) (CH3)3 CBr

> C3H6

(CH3)2 C(OH) CH3

[ 3 marks]
(b) State the conditions necessary for the conversions in
(i) (a) (i) above

(ii) (a) (ii) above.

[ 2 marks]
(c) Write the equations for the steps involved in the conversion shown in
(i) (a) (i) above

[ 3 marks]

(ii) (a) (iii) above.

[ 2 marks]
Total 10 marks

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nn')ti71 Jr A PR/F 9003

- 12 -

6. (a) (i) Write the structural formulae of TWO products formed when methylbenzene is
treated with a mixture of concentrated nitric acid and concentrated sulphuric acid.

[ 2 marks]
(ii) Write the equations showing the steps involved in the formation of ONE of the
products identified in (a) (i).

[ 2 marks]
(b) Give an explanation for EACH of the following:
(i) Methylbenzene is more susceptible to electrophilic attack than benzene.

[ 1 mark]
(ii) The 2-position on the methylbenzene ring is attacked by electrophiles more readily
than the 3-position.

[ 1 mark ]
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(c) For EACH of the following pairs of compounds , state ONE simple chemical test that can
be used to distinguish between them.
OH
(i) Ethanol and phenol

[ 1 mark ]
OH
(ii) Phenol

(6 and ethanoic acid CH3 C

O - H

[ i mark ]
(d) Account for the differences in acidity between ANY ONE of the pairs of compounds
given below.
EITHER

OH

Ethanol CH3CH2OH and phenol

OR
OH
O
Phenol (6 and ethanoic acid CH3
O - H

[ 2 marks]
Total 10 marks
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MODULE 3
Answer ALL questions
7. (a) Explain what is meant by `calibration'.

[ l mark]
(b) Distinguish between `precision' and `accuracy' of measurements.

[ 2 marks]
Table 3 below shows the readings obtained during the calibration of a 25 cm3 pipette. During the
calibration exercise the masses of 25 cm3 samples of water were recorded. The volumes of the
equilibrated water used were then determined using the density of water with a correction for
buoyancy error.

TABLE 3: CALIBRATION READINGS


Sample

Volume (cm)

1
2
3
4

25.008
25.006
25.017
25.010

5
6
7
8
9
10

25.009
25.015
25.007
25.008
25.015
25.006

(c) Using the data in Table 3, calculate the following:


(i) Mean volume delivered by the pipette

(ii) Standard deviation

[ 4 marks]

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(d) Using your answers to (c) on page 14, state the capacity of the pipette.

[ 1 mark]
(e) What additional measurement would have been necessary for the conversion of mass to
volume? Explain your answer.

[ 2 marks]
Total 10 marks

8. Spectroscopy is an essential tool in modern methods of analysis especially in the area of structure
elucidation. The natural product methyl salicylate absorbs in the ultraviolet region at a wavelength
of 240 nm.
(a) Explain, with an illustration , the type of excitation that occurs on absorption of UV radiation.

[ 2 marks]
(b) Give TWO features of UV radiation in relation to its position in the electromagnetic
spectrum.

[ 1 mark ]

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(c) Select any chromophores in methyl salicylate, P, that could be responsible for the absorption at this wavelength.
OH
COOCH3

[ 2 marks]
(d) Methyl salicylate, (P), can be extracted from the plant Gaultheria fragrantissima. A
10.0 g sample of dried and powdered bark was subjected to solvent extraction using ethyl
acetate. The volume of extract was then reduced and separation techniques used to obtain
a sample of P in solution. A 1 cm3 sample of the final solution containing P showed an
absorbance of 0.85 at a wavelength of 240 nm (absorptivity constant = 12000) and 1 cm
cell path.
(i) Use Beer-Lambert's Law to calculate the molar concentration of methyl salicylate
in the 1 cm3 of solution.
r

[ l mark]
(ii) Calculate the mass concentration of methyl salicylate in the solution.

[ 2 marks]
(iii) Given that the total volume of the final solution containing P was 10 cm3 , calculate
the percentage of methyl salicylate in the plant sample.

[ 2 marks]
Total 10 marks
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9. Chromatography can be used to separate mixtures of organic or inorganic molecules.


Chromatographic methods involve the use of a mobile phase and a stationary phase.
(a) State the general principle upon which chromatography is based.

[ 1 mark ]
(b) Describe and give ONE example of (i) mobile and (ii) stationary phase.
(i) mobile phase

Example

[ 2 marks]
(ii) stationary phase.

Example

[ 2 marks]

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(d) The chromatogram below was obtained on analysis of a liquid, A, by elution chromatography.

LA
Time

(i) Use the chromatogram to comment on the nature of A.

[ 3 marks]
(ii) Explain the difference in the retention times of Y and Z.

[ 2 marks]
Total 10 marks

END OF TEST

nn?67I ICAPP/F 2003