NAME: Tung LA

TEACHER: ANDS JONS NISH

(highlight one of these)

WELLINGTON SECONDARY COLLEGE

Unit 4 Chemistry
SCHOOL ASSESSED COURSEWORK ONE
Reaction Pathways and Analytical Chemistry Structured Questions

Friday 4th September, 2020 (3:30pm – 5:20pm)

Download Time: 10 minutes
Reading Time: 10 minutes
Writing Time: 80 minutes
Upload Time: 10 minutes

QUESTION AND ANSWER BOOK

Structure of Book

Number of
Number of Number of
Section Answers questions to
questions marks
be answered

Section A Highlight correct option 5 5 5

Section B Type response in textboxes 4 4 22
Section C Complete on a blank piece of paper 2 2 28
Total 55

Materials Allowed:
• Students are permitted to bring into the SAC room: pens, pencils, highlighters, erasers, sharpeners, rulers,
scientific calculator and VCAA data booklet
• Students are NOT permitted to bring into the SAC room: textbooks, notes, blank paper or white out
Instructions:
• Type your name in the space provided above and highlight your teacher’s initials
• All written responses must be in English.
• All responses are to be typed into this booklet in the textboxes provided

Students are NOT permitted to have mobile phones and/or any other unauthorised electronic devices in
the assessment room.

Authentication Statement:
I hereby declare the work I am submitting is my own work and not from any external assistance (i.e. internet, notes, text
book or another person). I have read and understood the WSC and VCAA policies on authentication and state that the
work uploaded is my own. If any discrepancies arise, I understand the process of breaching the authentication rules and
that the incident will be reported to Senior School.

Signed: Tung LA Date: 4th September 2020

1
SECTION A – Multiple-Choice Questions
Instructions for Section A
Highlight the response that is correct or that best answers the question.
A correct answer scores 1; an incorrect answer scores 0.
No marks will be given if more than one answer is completed for any question.

Question 1
The high resolution proton NMR of the compound (CH3)3CCOCH3 would show:
A. Two singlets
B. Two triplets

if
C. Two quartets
c
D. Four quartets

Question 2
Name the family of organic compounds that the following compound belongs to:

A. Alcohol
B. Ketone
C. Aldehyde

I
D. Ester
x
Question 3
The following reaction between cyclohexene and bromine is classified as

A. Addition
B. Substitution
C. Condensation
D. Hydrolysis

1
The carbon attached
Question 4
The alcohol on the right is classified as a:
The hydroxyl group
A.
B.
Primary alcohol
Secondary alcohol at is bonded to
C. Tertiary alcohol
0
D. Quaternary alcohol 3 other Carbone

Question 5 Tertian
How many hydrogen atoms are there in one molecule of 3-hydroxybutanoic acid?

Q
EITI
A. 7 B. 8 C. 9 D. 11

2
fatsos I
SECTION B – Short Answer Questions
Instructions for Section B
Answer all questions in the textboxes provided.
Ensure chemical equations are balanced and that the formulas for individual substances include an indication of
state, for example, H2(g), NaCl(s).

Question 1 (5 marks)
A particular chemical industry produces waste water contaminated with organic solvents. Analysis by high performance
liquid chromatography (HPLC) identified which solvents were present. The results of the analysis are shown below.

(a) State one change to the HPLC analysis that would decrease the retention time of all the organic solvents. 1 mark

Yeast T pressure of mobilephase

T temp
(b) Two substances have different retention times under identical conditions using the same HPLC equipment. Explain
this difference in retention times. 3 marks

Each moleales has different sizes and polarity and hence

different rat of adsorb and desorb into mobile phase
IJ a moleak he adsorb Onto the stationary
is strongly
phase it will have lower rate of movement Mere
higher retention tire
it
Polar moleales lower retention time meaning that
having
has spent more time adios to themobile phase isMobile a polar
(c) A standard solution of butanoic acid with a concentration of 250 mg L-1 is passed through the HPLC machine under
identical conditions and records a response of 225. What is the concentration of the butanoic acid in the waste water
in mg L-1? 1 mark

Peak rest
250mg y 225 sgjig
167 mall 150
3
 Question 2 (9 marks)
A chemist found in his laboratory a reagent bottle containing a liquid that was labelled with the molecular formula and
five structures of possible isomers of C4H8O2 (see below).

44 44

3M en

4 C env

3 C Je
The chemist decided to analyse this organic compound using NMR spectroscopy. She obtained the following spectra.

(a) The 1H-NMR spectrum shows three clear signals with distinctive splitting patterns. Use the table below to analyse
and interpret the proton NMR regarding the molecule C4H8O2. 4 marks

Information provided about structure of C4H8O2

Number of signals
(1 mark) 3 different hydrogen
environments

Quartet three neighbour hydrogen

Splitting pattern of
. Singlet no neighouring Hydrogen
each signal
(3 marks)
Triplet two neighboring hydrogens

(b) The C-NMR spectrum of this molecule shows four distinctive signals. State one piece of information that you can
obtain from this spectrum that helps you to identify the structure of the unknown molecule. 1 mark

Contai 4 carbon environments

4
(c) Combining all of the pieces of information from (a) and (b), determine which isomer from Figure 1 was in the bottle
(A – E) and name the compound. 2 marks
Saturation
test
oxidation test
C ethyl ethanoate Acid test

Acid Na co Coz trot Ngai

(d) Apart from having the same molecular formula, Chemicals A and B share a number of physical properties, including
high melting points and boiling points, high solubility in water and relatively high flashpoints and viscosity. In light
of this, describe a chemical test, including the results and chemical basis of the test, that could be used to distinguish
between chemicals A and B. 2 marks

T igyjj.gl ausithoIiodt
tertiaryalcohol
Acid test
Ma 03
carboxyl React both samples with
AUD co gas is released i mean s
a
Ig that
IS no gas bubbling the sample is acid
Question 3 (4 marks) Mio reactions Sampled Sample A
Amphetamine is chemically related to adrenalin, the ‘fight or flight’ hormone. Amphetamines were used initially as a
treatment for sleep disorders. Their short-term effects include an increase in heart rate and breathing rate. Long-term
effects include emotional instability. A related compound is methylenedioxymethamphetamine – MDMA (ecstasy). The
structures of adrenaline, amphetamine and MDMA are shown below.

(a) Name one functional group that is found in adrenaline but is not found in amphetamine or MDMA. 1 mark

04 Hydroxyl group

(b) Describe how this functional group would be observed on an infrared spectrum. 1 mark

A strong band at 3200 3600in

(c) State which of the three structures will be most soluble in water and explain your reasoning.
MHz 2 marks

Adrenaline will be most soluble in water.

All 3 molecules have polar structure with a benzene ring and an amino functional group,
however, Adrenaline has the highest number of hydroxyl functional groups, which is able
to form Hydrogen bond with water. The hydrogen bonds are stronger than the
dispersion force from the alkyl group in amphetamine and MDMA, hence it can breaks
the hydrogen bond between water molecules and be soluble.

5
 Question 4 (4 marks)
An organic compound with molecular formula, C4H8O, is analysed using NMR and IR spectroscopy. The IR spectrum
of the compound is shown below.

( (a) State a functional group that is most likely present in the compound. 1 mark
or
of carbonyl
I
The high-resolution proton NMR spectrum of the compound is shown below, with the splitting patterns magnified.

doublet
Only I oxygen
singlet
Lonely'peat septet

I 10ppm
Aldehyde

(b) Identify the chemical environment represented by the peak at 9.7 ppm: 1 mark

CI or Remo
(c) Based on the information above, determine the identity of the molecule and write its semi-structural formula below.
1 mark

g act CHO a
Eid
in
(d) Based on your answer to (c) what is the ratio of the areas under each of the three peaks? 1 mark

6 1 1 6
 SECTION C – Pathways and Calculations
Instructions for Section C
Answer all questions on a BLANK PIECE OF PAPER.
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.
Give simplified answers to all numerical questions, with an appropriate number of significant figures

Question 1 (16 marks)

Propane is an important gas and is used almost everywhere, for example to heat our homes & hot water, cook food,
power BBQs and fuel cars. Propane can be used as a starting material to produce propanoic acid.
(a) Complete the flowchart below to propose a reaction pathway for the synthesis of propanoic acid. Indicate semi-
structural formulas and name all organic molecules using the IUPAC system. 3 marks

Substitution Substitution

CHINCH UV light
Azhar'zCI CHCH HGH

I chloropropane
6 propan a ol

Oxidant

I Alzate 110.4
at'Yadical
(b) Step 1 requires the use of UV light as a catalyst.
i. Name the type of reaction that occurs. 1 mark

__________________________________________________________________________________________

ii. What is the specific function of the light? 1 mark

Break Cia into free mourg radical

__________________________________________________________________________________________

iii. Other than various chlorinated hydrocarbons, write the chemical formula for the other compound that is formed
in this reaction. 1 mark

I
__________________________________________________________________________________________

iv. One of the possible products of this reaction has the chemical formula C3H7Cl. Draw the structural formulas
of the possible isomers of C3H7Cl and give the name of the one that has the lowest melting point. 2
marks

Isomer Lowest
meltingpoint 2 chloropropan

ÉÉn Idlest da more dilica

for Cl to Jo 7

dipole due to thesurrounded

 (c) List the reagents and conditions required for each of the following steps: 2 marks

NaOH
Step 2: ________________________________________________________________

and theaters
Herzog
Step 3: ________________________________________________________________

(d) The concentration of propanoic acid produced via the above reaction pathway can be calculated via titration with a
standardised solution of sodium hydroxide.
i. Write a balanced chemical equation for the reaction between propanoic acid and sodium hydroxide. 1 mark

___________________________________________________________________________________________
CHzCHzCOOHCagytmaoHCaqy ctlzctlzCOONala.lt ACD
ii. A 20.00 ml aliquot of aqueous propanoic acid is neutralised by 8.60 mL of the 0.100M sodium hydroxide solution.
Given this information, calculate the concentration of the solution of propanoic acid. 2 marks

It 0.00860 8.6 15 mal

__________________________________________________________________________________________
0.100
Naoh
__________________________________________________________________________________________

not
gwyn Mnaon 0
__________________________________________________________________________________________
I
Mpropanui 8.6
1
I
__________________________________________________________________________________________
C 881 0.0430M
iii. Convert the concentration calculatedacid
in ii. into parts per million (ppm). 1 mark

1 Lt 0.0430mot
E ng
in
ppm __________________________________________________________________________________________
lg jpg gg 3I7
iv. Suggest an appropriate indicator that could have been used during this titration and state the colour change that
would be observed at the end point of the reaction. 2 marks
_________________________________________________________________________________________
Phenolphtalein
_________________________________________________________________________________________
Colourless
pink
(e) Name another analytical technique that could be used to determine the concentration of a sample of propanoic acid.
Outline the steps that would need to be followed. 3 marks

HPL Run with know

____________________________________________________________________________________________
a sample conc
____________________________________________________________________________________________
Measure the peak knows
area of
then establish calibration are
____________________________________________________________________________________________

Run thinksarple ad Fid its peak area

____________________________________________________________________________________________

make sure they should be in identical contionwith some

____________________________________________________________________________________________

retention
____________________________________________________________________________________________
tied
Measure peak area and the us corn to interpolate
Question 2 (13 marks)
and fit the cone
The iron content in a newly developed steel frying pan was determined by dissolving a 4.30 g sample of steel in 10M
hydrochloric acid and making up the resulting pale green solution of Fe 2+ ions to 250.00 ml, using a standard volumetric
flask. 20.00 ml aliquots of this solution were then titrated against a standard solution of 0.030M potassium permanganate
(KMnO4) solution, which is purple in colour. The solution of Mn2+ and Fe3+ ions produced by the reaction was almost
colourless.
Four titrations were carried out and the volumes of KMNO4 solution used were recorded in the table below.

Titration number 1 2 3 4

IÉÉÉÉ9iont
concordant 8
 Volume of KMnO4 (mL)
0
14.05 14.55
a 0
13.97
0
13.99

a. Write a full balanced equation of iron reacting with concentrated hydrochloric acid. 1 mark

Fees ancican Fegan

____________________________________________________________________________________________
t y
b. Write an overall balanced equation for the titration reaction.
É 2 marks

5FeY 8th.nl FeYaaptMitagthMa0

____________________________________________________________________________________________
Madinat
____________________________________________________________________________________________

____________________________________________________________________________________________

c. Calculate the average volume, in mL, of the potassium permanganate solution used in this titration. 1 mark

13.97 is or
____________________________________________________________________________________________
14.00mi
13.94
____________________________________________________________________________________________

d. Use your answer to part c. to calculate the amount, in mol, of MnO4– (aq) ions used in this titration. 1 mark

CV Y
G 030 0.0160
____________________________________________________________________________________________

moi 4.2415 not

____________________________________________________________________________________________

e. Calculate the amount, in mol, of Fe2+(aq) ions present in the 20.00 mL aliquot solution. 1 mark
____________________________________________________________________________________________
J minor
FI MII heart
____________________________________________________________________________________________

f. Calculate the amount, in mol, of Fe2+(aq) ions present in the 250.0 mL volumetric flask.
0.0021 not
1 mark

front
____________________________________________________________________________________________
250th
0.0
I I
a
naw
250 0.02
____________________________________________________________________________________________
1
g. Calculate the percentage, by mass, of iron in the 4.30 g sample of alloy. Express your answer to the correct number
of significant figures. 3 marks
0 07625
1
____________________________________________________________________________________________
m
nee Ie 55.8
____________________________________________________________________________________________ t.IE
0.02675
Mfe
____________________________________________________________________________________________
1.4791
____________________________________________________________________________________________
34
h. An indicator was not required for this titration. Why not? 1 mark

Mnd natural
____________________________________________________________________________________________
change its colour once red e
Purple Colourless
____________________________________________________________________________________________

i. A pipette is used to transfer the 20.00 mL aliquots of the solution. Each time, prior to obtaining an aliquot, the pipette
is rinsed with distilled water. Explain, how this will affect the percentage of iron in the sample. 2 marks

sample aliquot t
____________________________________________________________________________________________
conc in
of t
____________________________________________________________________________________________
Con
Fit
titre is required
____________________________________________________________________________________________
Less volume
of 9

Fa t
End of Assessment Task

10