Student Name: ____________________________________________________________

CHEMISTRY 2019
Unit 4
Key Topic Test 3 – Instrumentation and organic chemistry

Recommended writing time*: 45 minutes

Total number of marks available: 50 marks

QUESTION BOOK

* The recommended writing time is a guide to the time students should take to complete this test.
Teachers may wish to alter this time and can do so at their own discretion.

 TSSM 2019 Page 1 of 1

2019 CHEMISTRY KEY TOPIC TEST

Conditions and restrictions

Students are permitted to bring into the room for this test: pens, pencils, highlighters,
erasers, sharpeners and rulers. The Chemistry Data Book may be used.
Students are NOT permitted to bring into the room for this test: blank sheets of paper
and/or white out liquid/tape.
A scientific calculator is permitted in this test.

Materials supplied
Question and answer book of 15 pages.

Instructions
Print your name in the space provided on the top of the front page.
All written responses must be in English.

Students are NOT permitted to bring mobile phones and/or any other unauthorised
electronic communication devices into the room for this test.

 TSSM 2019 Page 2 of 2

2019 CHEMISTRY KEY TOPIC TEST

SECTION A – Multiple-choice questions

Instructions for Section A

Answer all questions.
Choose the response that is correct or best answers the question.
A correct answer scores 1, an incorrect answer scores 0.
Marks are not deducted for incorrect answers.
If more than one answer is completed for any question, no mark will be given.

Question 1
The mass spectrum of an unbranched alkane has a molecular ion peak of m/z = 86. The molecular
formula and name of the alkane is:

A. C5H10, pentane
B. C6H14, hexane
C. C4H10, butane
D. C4H10, methyl propane

Question 2
The mass spectrum below represents a ketone. Which one is it?

A. Butanone
B. Propanone
C. Pentan-2-one
D. Hexanone

 TSSM 2019 Page 3 of 3

2019 CHEMISTRY KEY TOPIC TEST

Question 3
The structure and infrared spectrum of vitamin C are shown below:

The peaks at wavenumber 1674 and 1322 represent, respectively:

A. an aldehyde and an alcohol group

B. an alcohol and an alkene group
C. an alkene and an alcohol group
D. an alcohol and a ketone group

Question 4
A non-polar solvent is used in HPLC with a polar stationary phase. A sample of propanoic acid
injected into the column will travel

A. slowly as the propanoic acid will easily adsorb onto the stationary phase.
B. slowly as the propanoic acid will dissolve easily in the mobile phase.
C. quickly as the propanoic acid will dissolve readily in the mobile phase.
D. quickly as the propanoic acid will not adsorb easily onto the stationary phase.

 TSSM 2019 Page 4 of 4

2019 CHEMISTRY KEY TOPIC TEST

Questions 5 and 6 refer to the following calibration curve from measuring the blood plasma
amount of the hormone molecule cortisol per mL in pmol ( 1 pmol = 10-12 mol)

Question 5
Select the alternative that would best describe the nature of this testing.

A. Example of thin layer chromatography. The area under the peak increases with concentration.
B. Example of HPLC. The retention time will be used to determine concentration.
C. Example of HPLC. The area under the peak will be used to determine substance identity.
D. Example of HPLC. The areas under the peak can be used to help determine concentration.

Question 6
The chemically-determined stress levels of a patient at a hospital were measured by analyzing a
sample of their blood for cortisol level.

1 mL of blood was diluted to 100 mL then put through the machine that had produced the above
calibration curve for cortisol samples with known concentrations. The area count obtained from
the diluted blood sample was 305.

The mass of cortisol in the sample of blood was, in pmol:

A. 3950
B. 5170
C. 39500
D. 51700

 TSSM 2019 Page 5 of 5

2019 CHEMISTRY KEY TOPIC TEST

Questions 7 and 8 refer to the following molecule

Question 7
Under carbon-13 NMR the molecule shown will have

A. 2 different carbon environments.

B. 3 different carbon environments.
C. 4 different carbon environments.
D. 5 different carbon environments.

Question 8
Under 1H high resolution NMR the molecule shown will have included in its spectrum:

A. only 2 different main peaks

B. only 3 different main peaks
C. 2 peaks split in 4
D. 3 peaks split in 4

Question 9

The m/z ratios of 49 and 84 in the above mass spectrum respectively represent:

A. CH2Cl+ and CH2Cl2+

B. CHCl+ and CH3Cl+
C. CH2+ and CHCl+
D. CH2Cl2+ and CCl2+

 TSSM 2019 Page 6 of 6

2019 CHEMISTRY KEY TOPIC TEST

Question 10
The UV spectrum of different concentrations of ethanol is shown below.

For this spectrum:

A. A calibration curve can be drawn to determine the concentration of ethanol in a solution

B. Peak heights shown here represent the concentrations of ethanol
C. No information can be drawn as there is a peak to the left of 400 nm
D. Peak heights shown here are proportional to the concentrations of ethanol

 TSSM 2019 Page 7 of 7

2019 CHEMISTRY KEY TOPIC TEST

SECTION B - Short-answer questions

Instructions for Section B

Questions must be answered in the spaces provided in this book.
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 workings in your answers to numerical questions. No credit 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
The chromatogram is shown below was obtained from analysing a mixture that was introduced
into a HPLC column:

i. How many components are there in the mixture? Explain.

________________________________________________________________________

________________________________________________________________________
2 marks
ii. Which of the components would be the most water-soluble? Explain.

________________________________________________________________________

________________________________________________________________________
2 marks

 TSSM 2019 Page 8 of 8

2019 CHEMISTRY KEY TOPIC TEST

iii. How could peak (a) be used as a qualitative measure in this HPLC analysis?

________________________________________________________________________

________________________________________________________________________
1 mark

iv. How could peak (a) be used as a quantitative measure in this HPLC analysis?

________________________________________________________________________

________________________________________________________________________
1 mark
v. A researcher wants to determine the concentration of the substance with the peak labelled
Explain how the researcher might achieve this objective.

________________________________________________________________________

________________________________________________________________________
2 marks
vi. Would the solvent used in this HPLC analysis be more likely to be hexane or methanol?
Explain
________________________________________________________________________

________________________________________________________________________
2 marks
vii. What is meant by the phrase “adsorbed onto the stationary phase”? Give your answer in
context of the HPLC analysis referred to here

________________________________________________________________________

________________________________________________________________________
1 mark

2 + 2 + 1 + 1 +2 + 2 +1 = 11 marks

 TSSM 2019 Page 9 of 9

2019 CHEMISTRY KEY TOPIC TEST

Question 2
The mass spectrum of a hydrocarbon is given below;

a. Knowing that the molecule is an alkane, suggest possible structures that have caused peaks
with m/z ratios of

i. 57__________ ii. 43 _______

iii. 29__________ iv. 15 _______

4 marks
b. i. Write the semi-structural formula and name of this molecule.

_____________________________________________________________________________
2 marks

i. Write an equation for the ionisation of this molecule.

___________________________________________________________________________
1 mark

2 + 1 = 3 marks

Total 7 marks

 TSSM 2019 Page 10 of 10

2019 CHEMISTRY KEY TOPIC TEST

Question 3
The molecule propanoic acid was analysed by four methods to reveal aspects of its structure
using mass spectrometry, 1H NMR , Carbon-13 NMR and infra-red spectroscopy,

a. Below is the mass spectrum for propanoic acid:

i. Write down the semi-structural formula of propanoic acid

________________________________________________________________________

What does the peak at m/z = 57 represent?

________________________________________________________________________

________________________________________________________________________

ii. What does the peak at m/z = 29 represent?

________________________________________________________________________

________________________________________________________________________
1 + 1 + 1 = 3 marks

 TSSM 2019 Page 11 of 11

2019 CHEMISTRY KEY TOPIC TEST

b. Below is the 1H NMR spectrum for propanoic acid

i How many chemical environments for hydrogen are shown on the above NMR spectrum?
Explain.

_________________________________________________________________________
2 marks

ii Draw the full structural formula for propanoic acid below and write an * next to each
hydrogen that has a unique chemical environment in the molecule

3 marks

iii At a much finer resolution, it is noted that the peak at 2.3 ppm is actually composed of four
peaks close together. Use the n+1 rule to explain what this reveals about the structure of
propanoic acid

_________________________________________________________________________

_________________________________________________________________________

3 marks
2 + 3 + 3 = 8 marks

 TSSM 2019 Page 12 of 12

2019 CHEMISTRY KEY TOPIC TEST

c. Below is the Carbon-13 NMR spectrum for propanoic acid

i How many chemical environments for carbon are shown on the above NMR spectrum?
Explain using the term chemical shift in your answer .

_________________________________________________________________________
3 marks

ii Draw the full structural formula for propanoic acid below and write an * next to each carbon
that has a unique chemical environment in the molecule

3 marks
3 + 3 = 6 marks

 TSSM 2019 Page 13 of 13

2019 CHEMISTRY KEY TOPIC TEST

d. Below is the infra-red spectrum for propanoic acid

Wave number 3000 cm-1 1750 cm-1

i What does the broad peak at wave number 3000 cm-1 indicate?

___________________________________________________________________________
1 mark

ii What does the broad peak at wave number 1750 cm-1 indicate?

_____________________________________________________________________________
1 mark
1 + 1 = 2 marks
Total 19 marks

 TSSM 2019 Page 14 of 14

2019 CHEMISTRY KEY TOPIC TEST

Question 4

butanal and butanone are structural isomers.

i. Draw both molecules.

2 marks

ii. How will the carbon environments compare between the two molecules?

___________________________________________________________________________
1 mark

2 + 1 = 3 marks
Total 3 marks

END OF KEY TOPIC TEST

 TSSM 2019 Page 15 of 15