CURTIN UNIVERSITY OF TECHNOLOGY

DEPARTMENT OF APPLIED CHEMISTRY

FIRST SEMESTER EXAMINATION
JUNE 2002
Internal Students

UNIT: CHEMISTRY 123

INDEX NO: 07076

TIME ALLOWED: TWO (2) HOURS, preceded by a 10 minute reading period. The
supervisor will indicate when answering of the exam may begin. If
you wish to make notes, please use the back of your exam paper.

Total marks: 160

Before commencing the examination, please PRINT the following information

STUDENT NUMBER: ________________________________________

SURNAME: _________________________________________________

ALL OTHER NAMES: ________________________________________

AIDS ALLOWED: To be supplied by the candidate

Any make of scientific calculator or TEE approved graphic calculator.

GENERAL INSTRUCTIONS:

1. This paper contains TWO (2) sections, each equally weighted. You are recommended to
spend about 60 minutes on each part in the first instance.

2. ANSWER ALL questions in the space provided on the examination paper.

3. A sheet for rough calculations is provided on page 18 of this paper.

4. A list of formulae and constant values has been included on page 19 of this paper.

5. Write legibly IN INK, as illegible work may have to be typed at the candidate's expense.

Office use only

Question 1 2 3 4 5 6 7 8 9 10 Total
Part A
 First Semester Examination - Chemistry 123 - June 2002

Part B

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 First Semester Examination - Chemistry 123 - June 2002

PART A - PHYSICAL CHEMISTRY

Enough working must be shown to demonstrate the logic used in solving the
problems

1. On a 30˚C day an 80 L cylinder was pressurised to 20 atm with air (assumed to be

20 mole % oxygen and 80 mole % nitrogen).

Calculate the total pressure and the partial pressure of each of the gases after the air was
released into an 850 L chamber at 21˚C.

(7 marks)

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 First Semester Examination - Chemistry 123 - June 2002

2 A sample of a poisonous gas was collected in a 500 mL container at a pressure of 99.8

kPa and a temperature of 21˚C. The gas sample weighed 0.572 g.

(a) Calculate the molecular weight of the gas.

(5 marks)

(b) Calculate the average kinetic energy of the gas molecules.

(3 marks)

(c) What percentage of the gas molecules have an energy greater than this average
value? (If you did not get an answer to (b), you can assume a value of 2.00 kJ mol-1
for part marks).

(3 marks)

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 First Semester Examination - Chemistry 123 - June 2002

3. If a party balloon is filled with helium, it goes flat in 7.00 hours. How long will it stay
inflated if it is filled with hydrogen?

(6 marks)

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 First Semester Examination - Chemistry 123 - June 2002

4. Toluene C7H8(l) is found in petrol. It has a standard enthalpy of combustion of –

3909 kJ mol-1.

Given ∆Hof CO2(g) = -393.5 kJ mol-1 and ∆Hof H2O(l) = -285.8 kJ mol-1

(a) Calculate ∆Hof of toluene.

(4 marks)

(b) Calculate how much work is done on/by the toluene system during combustion of
one mole of toluene at 25˚C. State whether work is done on or by the system.

(6 marks)

(c) Calculate the change in internal energy of the system.

(2 marks)

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 First Semester Examination - Chemistry 123 - June 2002

5. The ∆Gof of toluene C7H8(l) is 117 kJ mol-1.

Given ∆Gof CO2(g) = -395 kJ mol-1

∆Gof H2O(l) = -237 kJ mol-1

(a) Calculate the standard free energy of combustion of toluene.

(5 marks)

(b) Use your answer to part (a) and the data for question 4 to find ∆So for the
combustion of toluene.

(3 marks)

(c) Comment on the significance of this value of ∆So.

(2 marks)

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 First Semester Examination - Chemistry 123 - June 2002

6. When a mammal becomes ill, it may develop a fever, i.e. the body temperature increases.
If the body temperature increased from 38.4˚C to 41.0˚C, what effect would this have on
the rate of a reaction which has a rate constant of 1.00 x 10-5 s-1 at 38.4˚C and an
activation energy of 14.5 kJ mol-1?

(7 marks)

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 First Semester Examination - Chemistry 123 - June 2002

7. The following kinetic data were obtained for the reaction

A(g) + 2B(g) → product

Initial concentration, mol L-1 Initial rate,

Experiment No [A]0 [B]0 mol L-1 s-1

1 0.60 0.30 12.6

2 0.20 0.30 1.4
3 0.60 0.10 4.2
4 0.17 0.25 ?

(a) Determine the rate law for this reaction.

(5 marks)
(b) What is the value of the rate constant?

(2 marks)
(c) Use the data to predict the reaction rate for experiment 4.

(2 marks)

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 First Semester Examination - Chemistry 123 - June 2002

8. The contribution to the destruction of the ozone layer caused by high-flying aircraft has
been attributed to the following mechanism:

Step 1. O3(g) + NO(g) → NO2(g) + O2(g)

Step 2. NO2(g) + O(g) → NO(g) + O2(g)

(a) Write the overall reaction.

(1 mark)

(b) Write the rate law for each elementary step.

(2 marks)

(c) What is the catalyst in the reaction?

(1 mark)

(d) What is the reaction intermediate?

(1 mark)

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 First Semester Examination - Chemistry 123 - June 2002

9. Organic chemists once used freezing point and boiling point measurements to determine
the molecular weight of substances they had synthesised. When 0.778 g of a non-volatile
compound is added to 100 g of benzene, the freezing point of the solution is found to be
0.307˚C lower than for pure benzene. Given that kf for benzene is 5.12 K kg mol-1, what
is the molecular weight of the synthesised compound?

(8 marks)

10. Wastewater from a sugar refinery contains sucrose (C12H22O11) as its main impurity at a
concentration of 3.42 g L-1. A project is set up to study the feasibility of removing the
sugar via reverse osmosis, where a pressure greater than the osmotic pressure is applied
to separate ions or molecules from an aqueous solution. What pressure must be applied
at 20˚C to produce pure water?

(5 marks)

END OF PART A

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 First Semester Examination - Chemistry 123 - June 2002

PART B - ORGANIC CHEMISTRY

1. (a) Ocimene is found in the essential oil of many plants. What is its correct IUPAC
name?

H3C
CH2
CH3 CH3

(3 marks)

(b) Draw the structure of trans-2,3-dichloro-2-pentene.

(3 marks)

2. Circle the asymmetric carbon atoms (chiral carbon atoms) in the structures below (some
compounds have more than one).

NH2
OH
H3C
COOH CH3CHCOOH
OH

Threonine Lactic acid

O
CH2OH
O
CH3 O
HO
CH3
CH3 CH2
HO OH

Nootkatone Vitamin C
(grapefruit oil)

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First Semester Examination - Chemistry 123 - June 2002

(4 marks)

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 First Semester Examination - Chemistry 123 - June 2002

3. Consider the following representations of molecules:

1 2 3

HO
H
H 3C CH3

H CH2CH 3
H

4 5 6

H 3C OH OH
C CH3
H 3C CH

CH3

7 8 9

CH2 H
H 2C CH2 H CH2CH 3

H 2C CH2 CH 3CH2 OH
CH2 H

10 11 12

H H H H
CH3
H C C C C O H
CH CH2
H C H H H 3C CH2 CH3
H H
H

(a) Identify all of the representations of 2-methylpentane: _____________________

(b) Identify all isomers of the molecule in representation 1: _____________________

(10 marks)

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 First Semester Examination - Chemistry 123 - June 2002

4. What alkenes could be used to prepare the following compounds?

dilute KMnO 4
OH
(a)
CH2OH

OH
(b) Br2 /H2O

Br

benzoyl peroxide
(c) H2C CH
catalyst n

(9 marks)

5. In the laboratory you treated cyclohexanol with concentrated phosphoric acid and, from
the reaction mixture, distilled a colourless liquid.

(a) Write an equation to illustrate the reaction involved.

(b) What type of reaction does this represent?

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 First Semester Examination - Chemistry 123 - June 2002

(5 marks)

6. In the laboratory you made a model of methylcyclohexane and investigated its

conformations. Draw the lowest energy conformation of methylcyclohexane and clearly
show and label the positions occupied by the methyl group and all hydrogen atoms.
Explain why your conformation is the most likely.

(5 marks)

7. Draw the Newman projection of 1-bromo-2-chloroethane in its lowest energy

conformation.

(3 marks)

8. Indicate above the arrow the reagents required to carry out the following transformations.

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 First Semester Examination - Chemistry 123 - June 2002

OH
(a) CH3
CH3

Br
(b)
CH3
CH3

(6 marks)

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 First Semester Examination - Chemistry 123 - June 2002

9. (a) Complete the equation for the addition reaction below.

H+
H2C CHCH3 + H2 O

(b) Write a mechanism for the above reaction showing intermediate species and the
movement of electrons. With the aid of this reaction mechanism, explain how
Markovnikov's Rule was able to predict the correct product.

(8 marks)

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 First Semester Examination - Chemistry 123 - June 2002

10. Complete any eight of the following reactions, giving the major organic product.

(a) CH3 HBr

Br 2
(b)
FeBr 3

1. O3
(c) CH3
2. Zn/H2O

H2O/H+
(d) HC CCH2CH2CH3
HgSO4

H2
(e) CH3
Ni

(f) Br 2

CH2 CH3
KMnO4 (excess)
(g)
heat

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 First Semester Examination - Chemistry 123 - June 2002

10. (cont.)

H2
(h) H3CC CCH2CH2CH3
Lindlar catalyst

Br 2 (1 mole)
(i) CH3 CH2CH2 CH3
hυ

HCl (1 mole)
(j) HC CCH2CH2CH3

HNO3
(k)
H2SO4

(24 marks)

END OF EXAMINATION

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First Semester Examination - Chemistry 123 - June 2002

ROUGH WORKING

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 First Semester Examination - Chemistry 123 - June 2002

DATA & FORMULA SHEET

P1V1 P2 V2 w = −P∆V k E Ê1 1ˆ
= ln 2 = − a Á − ˜
T1 T2 ∆E = q + w k1 R ËT2 T1 ¯
PV = nRT ∆G = ∆H − T∆S α b g
rate = k [A] [ B] [ C ]
rate A MWB q = nC m∆T 0
= P = χP
rate B MWA q = C∆T
∆T = kb m
KE = 3 2 RT q = mC s∆T
∆T = - k f m
E E
n − − a
= e RT k = Ae RT π = MRT
n0

0 0 0
∆H = ∆H f (products) − ∆H f (reactants) ∆G 0 = ∆G 0f (products) − ∆G 0f (reactants)

∆S 0 = ∆S 0f ( products ) − ∆S 0f (reactants ) ∆H = DE + PDV = DE + DnRT

CONSTANTS
R = 8.314 J K-1 mol-1 Cm,v(CH4) = 12.6 J mol-1 K-1
R = 0.0821 L atm K-1 mol-1 Cm,p(CH4) = 21.0 J mol-1 K-1
NA = 6.022 x 1023 mol-1 P0H2O (298K) = 3.14 kPa
1 atm = 101.3 kPa

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 First Semester Examination - Chemistry 123 - June 2002

PERIODIC TABLE OF THE ELEMENTS

QuickTime™ and a
Photo - JPEG decompressor
are needed to see this picture.

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