Student Name

Teacher HAL LLE LXI MDI

Chemistry Unit 4 SAC 1

AOS 1 Test - Analysis of second-hand data
(Concepts from AOS 1 - Ch 10 to 14)
Friday 25th of August, 2017
Reading time: 5 minutes
Writing time: 65 minutes
QUESTION AND ANSWER BOOK
Structure of book
Section Number of Number of Number of
questions questions marks
to be answered
A 11 11 11
B 4 4 41
Total 52

 Students are permitted to bring into the assessment session: pens, pencils, highlighters, erasers,
sharpeners, rulers and one scientific calculator.
 Students are NOT permitted to bring into the assessment session: blank sheets of paper and/or white
out liquid/tape.
Materials supplied
 Question and answer book of 14 pages, including answer sheet for multiple choice questions on pg 6.
 A data booklet (Please do not write in the data booklet)
Instructions
 Write your name and circle your teacher code in the space provided above on this page.
 All written responses must be in English.
 Do NOT write on the data book.
At the end of the assessment session
Wait silently for the supervisor to collect your question and answer booklet, and your data book.
 

Students are NOT permitted to bring mobile phones or electronic devices that are capable of
storing, receiving or transmitting information or electronic signals, such as recorded music and
video players, organisers, dictionaries and computerised watches and/or any other unauthorised
electronic devices into the assessment room.
Students must not disclose the contents of the task; to do so will be a breach of VCE guidelines and
will be dealt with according to VCAA regulations.
 
Balwyn High School Page 2 of 14 2017 Unit 4 SAC 1: AOS 1 Test
 
SECTION A: Multiple-choice questions

Instructions for Section A

Answer all questions in pencil on the answer sheet provided for multiple choice questions.
Choose the response that is correct or that best answers the question.
A correct answer scores 1, an incorrect answer scores 0.
Marks will not be deducted for incorrect answers.
No marks will be given if more than one answer is completed for any question.

Question 1
A drop that contains a mixture of three different organic compounds was applied to a thin layer
chromatography plate and developed using a suitable non-polar mobile phase. The final results are shown in
the image below.

compound A

compound B

compound C

The Rf value of the least polar component in this TLC separation is

A. 0.22
B. 0.30
C. 0.78
D. 0.80

Question 2
In a high-performance liquid chromatography (HPLC) experiment that uses a polar stationary phase together
with a non-polar mobile phase, which of the following molecules will have the greatest retention time?
A. Propanoic acid
B. 1-Propanol
C. Methyl propanoate
D. Propanone (CH3COCH3)
Balwyn High School Page 3 of 14 2017 Unit 4 SAC 1: AOS 1 Test
 
Question 3
The chromatogram below was obtained by analysis of a sample of a mixture of two alkanes (A and B) by
reverse-phase high performance liquid chromatography (reverse-phase HPLC). Reverse phase HPLC uses a
polar mobile phase and a non-polar stationary phase.

Which of the following changes will increase the retention time of compound B
A. increasing the pressure of the mobile phase
B. using a less tightly packed column
C. increasing the temperature
D. increasing the polarity of the mobile phase

Question 4
Which of the following properties is not of a primary standard.
A. Readily obtainable in a pure form
B. Have a known chemical formula
C. Be inexpensive
D. Have a low molar mass

Question 5
Which of the following compounds exists as a cis-trans isomer?
A. CHCl=CHBr
B. CH2=CBrCH3
C. (CH3)2C=CHCH2CH3
D. CH2=CH2

Question 6
Alkanes can be reacted to form alkenes. Decane can be reacted to form two products via the following
equation:
C10H22  C2H4 + C8H18
If only the alkene product can be sold for future use, what is the atom economy of this process?
A. 19.7 %
B. 50.0 %
C. 80.3 %
D. 100 %
Balwyn High School Page 4 of 14 2017 Unit 4 SAC 1: AOS 1 Test
 
The following information refers to Questions 7 and 8
Question 7
The graph below shows the change in pH of a solution during a titration of 20 mL of an unknown solution of
methanoic acid (HCOOH) with 0.10 M NaOH.

A suitable indicator for the titration and the colour change observed is
Indicator colour change observed
A. methyl red yellow to red
B. methyl red red to yellow
C. phenolphthalein colourless to pink
D. phenolphthalein pink to colourless

Question 8
To ensure that the glassware is completely clean, it must be rinsed before a volumetric analysis. Which of the
following experimental errors will result in an overestimation of the concentration of methanoic acid in the
unknown sample?
A. Rinsing the conical flask where the unknown solution will be placed with the 0.10 M NaOH standard
solution
B. Rinsing the 20 mL pipette with deionised water before measuring the unknown solution
C. Rinsing the burette with deionised water before adding the 0.10 M NaOH standard solution
D. Rinsing the 20 mL pipette with the 0.10 M NaOH standard solution before measuring the unknown
solution
Balwyn High School Page 5 of 14 2017 Unit 4 SAC 1: AOS 1 Test
 
Question 9
The diagram below shows the structure of a bromoethane molecule.

Which of the following compounds (I, II and III) is an enantiomer of the bromoethane shown above?

A. I
B. Both I and II
C. III
D. Bromoethane does not have an enantiomer

Question 10
How many chiral centres are present in the following molecule?

A. 0
B. 1
C. 2
D. 3

Question 11
The following molecule was run through a 1H NMR spectrometer.

The number of peaks and the splitting pattern you would expect to see on a high resolution 1H NMR spectrum
of this molecule would be:
A. 2 sets of peaks as a singlet and triplet
B. 2 sets of peaks as a doublet and a septet
C. 3 sets of peaks as a doublet and two quartets
D. 3 sets of peaks as a singlet, and two triplets
Balwyn High School Page 6 of 14 2017 Unit 4 SAC 1: AOS 1 Test
 
Section A Multiple Choice Answer Sheet
This answer sheet must not be detached from this booklet.

INSTRUCTIONS FOR MULTIPLE CHOICE ANSWER SHEET

Use a PENCIL for ALL entries. For each question, shade the box which indicates your answer.
Marks will NOT be deducted for incorrect answers.
NO MARK will be given if more than one answer is completed for any question.
If you make a mistake, ERASE the incorrect answer - DO NOT cross it out.

 
1 A B C D
 
2 A B C D
 
3 A B C D
 
4 A B C D

5 A B C D

6 A B C D

7 A B C D

8 A B C D

9 A B C D

10 A B C D

11 A B C D
Balwyn High School Page 7 of 14 2017 Unit 4 SAC 1: AOS 1 Test
 
SECTION B

Instructions for Section B

Answer all questions in the spaces provided. Write using black or blue pen.
To obtain full marks for your responses you should:
 Give simplified answers with an appropriate number of significant figures to all numerical questions;
unsimplified answers will not be given full marks.
 Show all working in your answers to numerical questions. No marks will be given for an incorrect
answer unless it is accompanied by details of the working.
 Make sure chemical equations are balanced and that the formulas for individual substances include an
indication of state; for example, H2(g); NaCl(s)
 
Question 1 (11 marks)
A sample of an unknown alcohol with the chemical formula C4H10O was analysed to determine its identity.
a. The unknown alcohol has four possible structural isomers. One of these structural isomers is drawn
below.
i. Provide the systematic name for structural isomer 1 in the box below.
(1 mark)
ii. Draw the structural formula of the other three isomers in the boxes below.
(3 marks)

Structural isomer 1: Structural isomer 2:

Systematic name: ___________________________

Structural isomer 3: Structural isomer 4:

Balwyn High School Page 8 of 14 2017 Unit 4 SAC 1: AOS 1 Test
 
b. The unknown alcohol was later identified as structural isomer 1. Describe a chemical test that could
be done to confirm the identity of the unknown alcohol as structural isomer 1.
(2 marks)

c. A mass spectrum of the unknown alcohol is shown below.

Relative intensity 

i. Write the chemical formula for the molecular ion.

(1 mark)

ii. On the diagram above, circle the base peak.

(1 mark)

iii. What is the most likely fragment that was lost from the molecular ion to produce the peak with
a m/z ratio of 59.
(1 mark)
Balwyn High School Page 9 of 14 2017 Unit 4 SAC 1: AOS 1 Test
 
d. A 1H NMR spectrum of the unknown alcohol is shown below.

Discuss whether the 1H NMR spectrum is consistent with the structure of structural isomer 1. Justify
your answer.
(2 marks)

Question 2 (9 marks)
Capsaicin is an organic molecule that produce the pungency, aroma and flavour of chili peppers. The
capsaicin content of peppers affects their quality, and it can be determined using HPLC.

The figure below shows the chromatogram of a 50 ppm capsaicin standard.

Detector signal 

a. What is the retention time of the sample?

(1 mark)
Balwyn High School Page 10 of 14 2017 Unit 4 SAC 1: AOS 1 Test
 
A series of standards with a concentration range of 5.00 to 50.0 ppm were analysed. The areas of the peaks are
shown in the table below.
Capsaicin standard (ppm) Peak Area

5.00 0.50
10.0 1.3
25.0 3.1
50.0 6.0

b. In the space provided draw a calibration curve including a line of best fit and all labels.
(4 marks)

c. The capsaicin content of a Jalapeño chili sample was then determined. 10.0 g of dry powder were
added into 100 mL of water and incubated for 1 hour in a sealed container to prevent loss of water.
After incubation, the sample was filtered. A 0.500 ml sample of the aqueous solution was combined
with 0.500 mL of water, and the final diluted sample was injected into the HPLC. The chromatogram
produced a peak with an area of 5.0.

i. Using the calibration curve from part b., determine the concentration of the diluted sample
injected into the HPLC.
(1 mark)

ii. Calculate the concentration of capsaicin in the original 100 mL extract.

(1 mark)
Balwyn High School Page 11 of 14 2017 Unit 4 SAC 1: AOS 1 Test
 
iii. Calculate the amount, in µg, of capsaicin in the 100 mL extract.
(1 mark)

iv. Calculate the concentration of capsaicin (in ppm) in the dry powder sample of Jalapeño chili.

(1 mark)

Question 3 (9 marks)

The concentration of ethanol (CH3CH2OH) in white wine can be determined by titration with a standard
solution of acidified potassium permanganate (KMNO4).

Ethanol, ethanoic acid and manganese ion (Mn2+) are all colourless chemicals. Potassium permanganate is a
purple solution.

The overall equation for this reaction is:

5CH3CH2OH (aq) + 4MnO4- (aq) + 12H+ (aq)  4Mn2+(aq) + 11H2O (l) + 5CH3COOH (aq)

a. Write a balanced half-equation for the reduction of potassium permanganate to Mn2+.

(1 mark)

b. Write a balanced half-equation for the oxidation of ethanol to ethanoic acid.

(1 mark)

c. What is the end-point of a titration? Explain how the end point is determined in this titration?
(2 marks)
Balwyn High School Page 12 of 14 2017 Unit 4 SAC 1: AOS 1 Test
 
d. A student titrates 10.00 mL aliquots of white wine with a 0.8500 M standard solution of potassium
permanganate. Titres of 30.50, 30.45, 30.48 and 29.10 mL were required to reach the end point. What
is the percentage (% m/v) concentration of ethanol in the white wine?
(5 marks)
 Balwyn High School Page 13 of 14 2017 Unit 4 SAC 1: AOS 1 Test
 
Question 4 (12 marks)
Compound X has the structural formula shown below.

a. In the diagram above, circle and label the name of the functional group in Compound X.
(2 marks)
b. Infrared spectra of two different samples are shown below.

Spectrum 1: Spectrum 2:

Transmittance 
Transmittance 

i. Which spectrum (1 or 2) is of Compound X?

(1 mark)

ii. Explain your reasoning to part bi. with reference to the presence and/or absence of
characteristic bands in both spectra.
(2 marks)
Balwyn High School Page 14 of 14 2017 Unit 4 SAC 1: AOS 1 Test
 
c. A reaction pathway is designed for the synthesis of Compound X. Complete the reaction pathway
below by:
i. Drawing the structural formula for Compound A in the box provided
(1 mark)
ii. Writing the systematic name for Compound B in the box provided
(1 mark)
iii. Writing the semistructural formula for Compound C in the box provided
(1 mark)
iv. Writing the conditions and reagents required for reaction II in the box provided
(1 mark)
v. Naming the reaction type for reaction I in the box provided
(1 mark)
vi. Write the chemical formula for the by-product of reaction III and IV in the boxes provided.
(2 mark)

Compound A
Structural formula: 

Reaction I: Conditions and reagents II:

H2O
H3PO4/catalyst/300 °C
1-Chloropropane

CH3CH2OH NH3

H+/Cr2O72-/heat By-product for Reaction III:

Compound B Compound C
Systematic name: Semi structural formula:

By-product for Reaction IV:

Compound X