Eduqas Paper 2

Centre Candidate
Surname
Number Number
First name(s) 2
GCE A LEVEL
O21-A410U20-1
A410U20-1
TUESDAY, 12 OCTOBER 2021 – MORNING
CHEMISTRY – A level component 2

Organic Chemistry and Analysis
2 hours 30 minutes
For Examiner’s use only
Maximum Mark
Question
Mark Awarded
ADDITIONAL MATERIALS
Section A 1. to 5. 15
In addition to this examination paper, you
A 41 0 U 2 0 1
will need a: Section B 6. 17
01
• calculator;
• Data Booklet supplied by WJEC. 7. 20
8. 17
INSTRUCTIONS TO CANDIDATES
Use black ink or black ball-point pen. Do not 9. 17
use gel pen or correction fluid. You may use
pencil for graphs and diagrams only. 10. 20
Write your name, centre number and
candidate number in the spaces at the top of 11. 14
this page.
Total 120
Section A Answer all questions.
Section B Answer all questions.
Write your answers in the spaces provided in this booklet. If you run out of space, use the additional
page(s) at the back of the booklet, taking care to number the question(s) correctly.
Candidates are advised to allocate their time appropriately between Section A (15 marks) and
Section B (105 marks).
INFORMATION FOR CANDIDATES

The number of marks is given in brackets at the end of each question or part-question.
The maximum mark for this paper is 120.
Your answers must be relevant and must make full use of the information given to be awarded full
marks for a question.
The assessment of the quality of extended response (QER) will take place in Q.8(a)(i) and Q.10(b).
OCT21A410U20101 © WJEC CBAC Ltd. PJ*(S21-A410U20-1)

2
Examiner
only
SECTION A
Answer all questions in the spaces provided.
1. Methylcyclohexane has been used as a component of correction fluid.
methylcyclohexane
(a) State the empirical formula of methylcyclohexane. [1]
(b) (i) A gas-liquid chromatogram of methylcyclohexane, contaminated with small

quantities of cyclohexane, ethylcyclohexane and propylcyclohexane is shown
below.
The figures show the relative peak areas.
Calculate the percentage of methylcyclohexane in the mixture. [1]
52
6
3 4
A B C D
Time / min
Percentage = %
02 © WJEC CBAC Ltd. (A410U20-1)

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(ii) The boiling temperatures of cyclohexane and some alkylcyclohexanes are shown
in the table.
Compound Boiling temperature / °C
cyclohexane 81
methylcyclohexane 101
ethylcyclohexane 131
propylcyclohexane 155
The retention times for these compounds become longer as the boiling temperature
rises.
State, giving a reason for your answer, which of the peaks A, B, C or D is likely to
be given by ethylcyclohexane. [1]
A 41 0 U 2 0 1
03
03 © WJEC CBAC Ltd. (A410U20-1) Turn over.

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2. Bromine reacts with phenylethene to produce (1,2-dibromoethyl)benzene.
CH CH2 + Br2 CHBr CH2Br
In an experiment 0.500 mol of phenylethene, together with a solvent, was placed in a flask and
bromine slowly added with constant stirring.
(a) Bromine is very hazardous and the quantity required is usually measured by volume.
The density of bromine is 3.16 g cm –3. Calculate the volume of bromine needed in this
reaction.[2]
Volume = cm3
(b) The melting temperature of pure (1,2-dibromoethyl)benzene is 73 °C. In the reaction the
product was recrystallised using ethanol as the solvent.
State how the melting temperature would differ if the product still contained traces of the
solvent.[1]

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3. 2,4-Dinitrophenol is a coloured solid that has been used in some illegal weight loss
preparations.
OH
NO2
NO2
2,4-dinitrophenol
Its visible spectrum shows a maximum absorption in the blue region of the electromagnetic
spectrum.
(a) State and explain the colour of this compound in white light. [1]
(b) This dinitro compound can be reduced to the corresponding diamino compound,
2,4-diaminophenol.
OH
NH2
NH2
2,4-diaminophenol
Suggest a reagent(s) that can be used for this reduction. [1]

7
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(c) A similar reaction can be used to produce 4-aminophenol, which can be used to make the
painkiller paracetamol.
OH OH OH
NO2 NH2 N CH3

H C
O
paracetamol
(i) State a compound that can be used in the second stage to make paracetamol. [1]
A 41 0 U 2 0 1
(ii) A solution of paracetamol is treated with a solution of bromine.
07
Give the colour change that occurs. [1]

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4. 0.774 g of the silver salt of an organic acid was heated and produced gaseous products and
0.365 g of solid silver.
O
R C Ag + gaseous products
O–Ag+
Use this information to calculate the relative molecular mass of the organic acid.[2]
Mr =

9
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5. The mass spectrum of butane-2,3-dione is shown below.
43
Relative
abundance
15 86
0
20 40 60 80 100
m/z
Draw the structure of butane-2,3-dione and use this to identify the molecular ion. Suggest
structures for the fragmentation ions. [3]
A 41 0 U 2 0 1
09
15

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SECTION B
Answer all questions in the spaces provided.
6. (a) Calcium propanoate, (CH3CH2COO)2Ca, is used as a preservative in bread making. On

heating it gives a ketone and calcium carbonate as the only products.
Complete the equation below, giving the structure of the ketone that is obtained. [1]
(CH3CH2COO)2Ca +
(b) Calcium propanoate (Mr 186) reacts with aqueous sulfuric acid giving propanoic acid and
calcium sulfate.
(CH3CH2COO)2Ca + H2SO4 2CH3CH2COOH + CaSO4
(i) In an experiment, 8.38 g of an impure sample of calcium propanoate reacted with

an excess of aqueous sulfuric acid, giving 5.70 g of calcium sulfate (Mr 136).
Calculate the percentage purity of the calcium propanoate, giving your answer to an
appropriate number of significant figures. [3]
Percentage purity = %

11
Examiner
3 only
(ii) After removal of insoluble calcium sulfate, 20 cm of hexan-1-ol was added to the
reaction product. Hexan-1-ol and water are immiscible.
The propanoic acid dissolved preferentially in the hexan-1-ol and the two layers
were separated using the apparatus below.
I. State the name of this piece of apparatus. [1]
II. Suggest how you could tell which was the hexan-1-ol layer. [1]
A 41 0 U 2 0 1
11
(iii) The hexan-1-ol layer, containing the dissolved propanoic acid, was then refluxed to
produce the ester 1-hexyl propanoate.
Give the equation for the reaction between propanoic acid and hexan-1-ol, to
produce the ester 1-hexyl propanoate. Show the structure of the ester. [2]
(c) At 0 °C the solubility of calcium propanoate in water is 49 g / 100 g of water. This rises to
56 g / 100 g of water at 100 °C.
Calculate the mass of calcium propanoate precipitated if a saturated solution of calcium

propanoate in 20 g of water is cooled from 100 °C to 0 °C. [2]
Mass = g

12
Examiner
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(d) Cysteine is a sulfur-containing α-amino acid.
C
HS OH
NH2
cysteine
(i) Write the displayed formula for cysteine. [1]
(ii) Cysteine reacts with hydrochloric acid to give the salt cysteine hydrochloride, which
is used in flour processing.
Suggest a skeletal formula for this salt. [1]
(iii) Cysteine contains a chiral centre and exists in two mirror image forms.
Draw the 3D structures of these two forms. [1]

13
Examiner
only
(e) Cysteine has been proposed as an antidote to counteract damage caused by excessive
ethanol consumption. It works by oxidising ethanal, which is produced from ethanol, to
ethanoic acid.
(i) The concentration of small quantities of ethanal present in ethanoic acid can be
measured by colorimetry, where the intensity of the colour produced in solution with
2,4-dinitrophenylhydrazine is measured at a wavelength of 480 nm.
Calculate the frequency of this absorption at 480 nm. [2]
Frequency = Hz
A 41 0 U 2 0 1
(ii) The absorption at 480 nm is related to the concentration of ethanal present by the
equation below.
13
absorption = constant × concentration
The absorption of an ethanal solution of concentration 5 × 10 –4 mol dm –3 is 1.25.
Find the concentration of a solution that gives an absorption reading of 0.70. [2]
Concentration = mol dm –3
17

14
Examiner
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7. (a) The condensation polymer Nylon-6 can be formed from 6-aminohexanoic acid.
Complete the equation for this reaction. [1]
H O
n ............................................................... N (CH2 ) 5 C + n ...........................
6-aminohexanoic acid Nylon-6
(b) (i) 6-Aminohexanoic acid is not readily available and Nylon-6 is made in industry by a
series of reactions starting with cyclohexane, which is first converted to cyclohexanol
and cyclohexanone.
OH O
O2
+ + non-organic products
catalyst
In an experiment only 5 % of the cyclohexane is oxidised and analysis of the organic

products shows that the molar ratio of cyclohexanol to cyclohexanone is 2:1.
If 2 400 mol of cyclohexane reacts in this way, calculate the mass of cyclohexanol
produced. Give your answer in kg. [3]
Mass of cyclohexanol = kg

15
Examiner
only
(ii) Cyclohexanone is then converted to Nylon-6 in a three-stage process.
OH
O N O
NH2OH acid NH water / 500 K

Nylon-6
acid increased
pressure
cyclohexanone caprolactam
oxime
I. In the first stage cyclohexanone reacts with hydroxylamine, NH2OH.
Suggest why hydroxylamine reacts as a nucleophile in this step. [1]
A 41 0 U 2 0 1
II. Use the Data Booklet to describe how the intensity of the infrared absorptions
change as cyclohexanone oxime is converted to caprolactam.
15
Refer only to the functional groups present and their absorption values.
The C–N infrared absorption is seen between 1 020 and 1 250 cm –1 and the
C=N infrared absorption is seen at 1 665 cm –1.[2]
III. In a batch process 200 kg of cyclohexanone oxime was converted to

caprolactam.
Explain why, if there is 100 % conversion of the oxime to caprolactam, exactly

200 kg of caprolactam will be obtained. [1]

16
Examiner
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(c) Another method of producing cyclohexanol is by the reduction of phenol.
OH OH
catalyst
+ 3H2
Apart from cost, state two factors that should be considered when choosing to make
cyclohexanol from phenol or from cyclohexane [as in part (b)(i)].[2]
1.
2.

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QUESTION CONTINUES
ON PAGE 18

18
(d) Cyclohexene can be produced in the laboratory by the dehydration of cyclohexanol.

This is done in the presence of sulfuric acid, which acts as a dehydrating agent.
OH
– H2O
boiling temperature boiling temperature

161 °C 83 °C
In an experiment cyclohexene was produced using the apparatus below.
fractionating
column
electric heater

19
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The mixture was heated electrically and the temperature at the top of the column was not
allowed to exceed 90 °C. Cyclohexene distilled over and was collected in the conical flask.
(i) Explain why the temperature at the top of the column was kept at 90 °C or below.
[1]
(ii) Suggest why the conical flask containing cyclohexene had a loose cotton wool plug
rather than being secured by a stopper. [1]
(iii) The cyclohexene distillate was not pure. Suggest and explain what other compound
could be present in the distillate. [2]
(iv) In the experiment 0.20 mol of cyclohexanol was dehydrated using sulfuric acid.
After purification 10 cm3 of cyclohexene was obtained.
A 41 0 U 2 0 1
Calculate the percentage yield of cyclohexene. [1]
19
1 mol of cyclohexene has a volume of 66 cm3
Percentage yield = %
(v) After the experiment the liquid left in the reaction flask contained unreacted
cyclohexanol, aqueous sulfuric acid and the compound whose formula is shown
below.
Suggest how this compound had been produced in the reaction. [1]

20
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(e) Cyclohexanone and liquid L are isomers of formula C6H10O. The label on the bottle
containing liquid L was torn but stated that it contained
‘…………methylpent-3-en-2-one’.
This meant that compound L was one of the two compounds whose formulae are shown
below.
H 3C CH3 H 3C H
C C C C
H C O H 3C C O
CH3 CH3
(i) 6.86 g of liquid L reacted with 0.070 mol of bromine (Br2) to give a new compound
of formula C6H10OBr2.
Use these quantities to show that this information fits both of the suggested
structures for compound L.[2]
(ii) Compound L reacts with hydrogen to give a saturated ketone, compound M.
I. Suggest the type of reaction mechanism occurring in this hydrogenation. [1]
II. The 1H NMR spectrum of ketone M suggested that it was

4-methylpentan-2-one.
Write the structure of compound L giving a reason for your answer. [1]
20

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22
8. (a) Benzylidene aniline is produced as a solid by heating together the liquids benzaldehyde
and phenylamine (aniline).
Starting with 0.040 mol of each reactant will result in about 6 g of the product.
H
H
C + H2N C N + H2O
O
benzylidene aniline
Reactant Mr Density / g cm –3
benzaldehyde 106 1.05
phenylamine 93 1.02
(i) The flow chart below outlines one method for its preparation.
product
mixture of solid + ethanol
benzaldehyde product
and phenylamine
boiling water
water 20 minutes
ice / water
heat heat
allow
crystals to
dry in air cold
filter crystals
water

23
Examiner
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Use the flow chart as a basis to write a more detailed method for the preparation of
6 g of this compound.
Your answer should state the volumes of the starting materials and a suggestion for
the volume of ethanol used for recrystallisation.
You should also indicate appropriate sizes of the glassware that you would use.
[6 QER]

24
Examiner
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(ii) The table below summarises two methods for making benzylidene aniline.
Reaction
Time taken Purification Yield
Method temperature Catalyst
/ min solvent /%
/ °C
1 2 20 FeSO4(s) ethanol 57
2 20 100 none ethanol 85
I. State one advantage of method 1 compared to method 2. [1]
II. State one disadvantage of method 1 compared to method 2. [1]
(b) The melting temperatures of the two isomeric hydroxybenzaldehydes are given below.
H H
O O
O H
C C
H O
1-2 °C 112-116 °C
Suggest reasons for this difference in melting temperature in terms of forces between
molecules and forces within molecules. [4]

25
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(c) Both benzoic acid and 2-hydroxybenzaldehyde have the formula C7H6O2.
(i) Complete the table below giving the observation, if any, for the reaction with each
of these compounds.
You can assume that the materials being used are in an appropriate solution.
If there is no reaction, you should write ‘no observation’. [2]
Reagent Benzoic acid 2-Hydroxybenzaldehyde
sodium
hydrogencarbonate ........................................................ ........................................................
alkaline iodine
........................................................ ........................................................
iron(III) chloride brown solid

........................................................
(ii) The brown solid produced when iron(III) chloride reacts with benzoic acid is iron(III)
benzoate.
Write the formula of this compound. [1]

.............................................................................................................................................
(d) Phenyl methanoate also has the molecular formula C7H6O2.
Give the structure of this compound and use it to explain why it is likely to give a silver
mirror when it reacts with Tollens’ reagent. [2]
17

26
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9. (a) The phenolic compound thymol has antiseptic properties.
CH3
OH
H 3C CH3
(i) Traditionally, thymol has been extracted from a number of plants, including the oil
obtained from the herb thyme. The solvent used for this extraction is ethanol or
dichloromethane.
In one extraction 5.5 g of thyme oil was obtained from 100 g of the plant.
On analysis the oil contained 12 % of thymol.
Calculate the concentration of thymol in the plant in mg g –1, giving your answer to
an appropriate number of significant figures. [2]
Concentration = mg g –1
(ii) Suggest why ethanol is seen as a ‘greener’ solvent for this extraction than
dichloromethane.[1]
(iii) Thyme oil contains a number of other compounds, including other phenols.
Most of these compounds, including the phenols, are colourless.
If a thin layer chromatogram is produced from this oil, the colourless spots have to
be made visible. When the thin layer plate is sprayed with a solution of a suitable
diazonium compound, the spots become coloured.
Explain why these spots now appear coloured. [2]

27
Examiner
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(iv) Another method of obtaining thymol is by the reaction of 3-methylphenol with
2-chloropropane in a Friedel-Crafts alkylation.
Give the equation for this reaction, stating any catalyst that might be used. [2]
(v) I. Suggest why thymol is only slightly soluble in water at room temperature. [2]
II. Thymol reacts with aqueous sodium hydroxide.
Suggest the formula of the organic compound that is produced. [1]

28
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(b) (i) State the name of the reagent that will convert 2-bromo-1,3-diphenylpropane into
1,3-diphenylpropene.[1]
H H H H H H
C C C C C C
H Br H H
2-bromo-1,3-diphenylpropane 1,3-diphenylpropene
(ii) Explain why 1,3-diphenylpropene can exist as E-Z isomers. [1]
(iii) Give the formula of the repeating section of the polymer that can be obtained from
1,3-diphenylpropene.[1]

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30
(iv) Study the reaction sequence below and answer the questions that follow.
CH2 C CH2
Br
Stage 1 reagent S
CH2 C CH2
CN
Stage 2
CH2 C CH2
CH2
NH2
compound T
(Mr 225)

31
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I. State the reagent S used in stage 1. [1]
II. State the type of reaction occurring in stage 2. [1]
III. Compound T reacts with nitric(III) acid in a 1:1 ratio giving nitrogen gas.
NH2 + HNO2 OH + N2 + H 2O
In an experiment, 200 cm3 of nitrogen was obtained at a temperature of 317 K

and at 1 atm pressure.
Show that the mass of compound T giving this volume was 1.73 g.
You must show your working. [2]
17

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10. (a) Hexamethylenetetramine (hexamine) is a solid that can be used as a fuel for camping
stoves.
N
N
N
(i) It can be made by reacting aqueous solutions of methanal and ammonia.
6CH2O + 4NH3 (CH2)6N4 + 6H2O

hexamine
Calculate the atom economy of this reaction to make hexamine. [2]
Atom economy = %
(ii) Both the high resolution 1H NMR and 13

C NMR spectra of hexamine show only a
single peak.
Suggest why these signals are single peaks. [1]
(iii) Hexamine acts as a tertiary base.
Explain the meaning of these two terms in this context. [2]
Tertiary
Base

34
(b) Four reactions are shown below. Each of them is wrong in some way.
For each of these reactions, explain what is incorrect, and correct them as appropriate.
[6 QER]
1. H H H H
UV light
H C C F H C C + F
H Cl H Cl
2. Cl OH
+ NaOH + NaCl
3. H H H H
H H
+ –
H C C C H Br H C C C + H
+
H H
H H Br
4. O H
C C OH
OH H
+ 8[H] + 2H2O
OH H
C C OH
O H
where [H] is NaBH4

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36
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(c) In an experiment, chlorine reacted with ethanoic acid to give a mixture of chloroethanoic
acid (CH2ClCOOH) and dichloroethanoic acid (CHCl2COOH).
4.75 g of this mixture of CH2ClCOOH and CHCl2COOH reacted with silver ions. The
chlorine present gave 8.83 g of silver chloride, AgCl.
(i) Calculate the percentage of chlorine in this mixture. [2]
Percentage = %

37
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(ii) Use the graph to find the percentages of chloroethanoic acid and dichloroethanoic
acid present in the mixture. [1]
56
54
52
50
48
Percentage
of chlorine 46
44
42
40
38
36
0 10 20 30 40 50 60 70 80 90 100
Percentage of dichloroethanoic acid
Percentage of chloroethanoic acid = %
Percentage of dichloroethanoic acid = %

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(d) Under suitable conditions dichloroethanoic acid, Cl2CHCOOH, reacts with alkalis to give
compound W.
Information about compound W is given below.
• It has a relative molecular mass of 74

• There are three oxygen atoms in each molecule
• Its 1H NMR spectrum shows signals at 9.5 and 11.0 ppm
• An aqueous solution turns Universal Indicator paper from green to red
• Its 13C NMR spectrum shows only two signals
Use all of this information to deduce a structure for compound W giving reasons for your
answer.[6]
20

39
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1 only
11. (a) The high resolution H NMR spectrum of a dimethylbenzene is shown below.
Explain how this spectrum shows that the compound is 1,4-dimethylbenzene. [3]
8.0 6.0 4.0 2.0 0.0

δ / ppm

40
Examiner
only
(b) 1,4-Dimethylbenzene (Mr 106) reacts with chlorine in a radical reaction to give
1,4-di(chloromethyl)benzene (Mr 175).
H3C CH3(I) + 2Cl2(g) ClH2C CH2Cl(l) + 2HCl(g)
In an experiment 0.240 mol of 1,4-dimethylbenzene reacted with chlorine.
Calculate the increase in mass of the liquid that corresponds to the formation of
1,4-di(chloromethyl)benzene.[2]
Increase in mass = g
(c) 1,4-Di(chloromethyl)benzene reacts with aqueous sodium hydroxide giving the

corresponding primary alcohol, 1,4-di(hydroxymethyl)benzene.
ClH2C CH2Cl + 2NaOH HOH2C CH2OH + 2NaCl
Use the diagram below to complete the mechanism, showing curly arrow(s), lone pairs
and any partial / full charges. [3]
H H
Cl C HO C + Cl
H H
HO

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(d) State the reagent(s) needed to convert 1,4-dimethylbenzene to benzene-1,4-dicarboxylic
acid, HOOC(C6H4)COOH.[1]
(e) 1,4-Di(hydroxymethyl)benzene, HOH2C–C6H4 –CH2OH, and benzene-1,4-dicarboxylic

acid, HOOC–C6H4 –COOH, react together to give a polyester.
(i) Use the formula of these two compounds to give the formula of the repeating section
of this polyester. [1]
(ii) Draw a ring around the part of the repeating section in part (i) that shows the ester
linkage in this polymer. [1]
(f) (i) State a reagent that can be used to convert benzene-1,4-dicarboxylic acid to the
corresponding diacyl chloride, benzene-1,4-dicarbonyl dichloride. [1]
(ii) The diacyl chloride reacts with ammonia to give the corresponding diamide and
ammonium chloride as products.
Give the equation for this reaction. [2]
14
END OF PAPER

42
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Centre Candidate

TUESDAY, 12 OCTOBER 2021 – MORNING

CHEMISTRY – A level component 2

INFORMATION FOR CANDIDATES

OCT21A410U20101 © WJEC CBAC Ltd. PJ*(S21-A410U20-1)

Answer all questions in the spaces provided.

1. Methylcyclohexane has been used as a component of correction fluid.

(a) State the empirical formula of methylcyclohexane. [1]

(b) (i) A gas-liquid chromatogram of methylcyclohexane, contaminated with small

The figures show the relative peak areas.

Calculate the percentage of methylcyclohexane in the mixture. [1]

02 © WJEC CBAC Ltd. (A410U20-1)

Compound Boiling temperature / °C

03 © WJEC CBAC Ltd. (A410U20-1) Turn over.

CH CH2 + Br2 CHBr CH2Br

04 © WJEC CBAC Ltd. (A410U20-1)

05 © WJEC CBAC Ltd. (A410U20-1) Turn over.

Suggest a reagent(s) that can be used for this reduction. [1]

06 © WJEC CBAC Ltd. (A410U20-1)

NO2 NH2 N CH3

07 © WJEC CBAC Ltd. (A410U20-1) Turn over.

08 © WJEC CBAC Ltd. (A410U20-1)

09 © WJEC CBAC Ltd. (A410U20-1) Turn over.

Answer all questions in the spaces provided.

6. (a) Calcium propanoate, (CH3CH2COO)2Ca, is used as a preservative in bread making. On

(CH3CH2COO)2Ca + H2SO4 2CH3CH2COOH + CaSO4

(i) In an experiment, 8.38 g of an impure sample of calcium propanoate reacted with

10 © WJEC CBAC Ltd. (A410U20-1)

I. State the name of this piece of apparatus. [1]

Calculate the mass of calcium propanoate precipitated if a saturated solution of calcium

11 © WJEC CBAC Ltd. (A410U20-1) Turn over.

(i) Write the displayed formula for cysteine. [1]

Suggest a skeletal formula for this salt. [1]

Draw the 3D structures of these two forms. [1]

12 © WJEC CBAC Ltd. (A410U20-1)

Calculate the frequency of this absorption at 480 nm. [2]

The absorption of an ethanal solution of concentration 5 × 10 –4 mol dm –3 is 1.25.

13 © WJEC CBAC Ltd. (A410U20-1) Turn over.

Complete the equation for this reaction. [1]

n ............................................................... N (CH2 ) 5 C + n ...........................

6-aminohexanoic acid Nylon-6

In an experiment only 5 % of the cyclohexane is oxidised and analysis of the organic

14 © WJEC CBAC Ltd. (A410U20-1)

NH2OH acid NH water / 500 K

I. In the first stage cyclohexanone reacts with hydroxylamine, NH2OH.

Suggest why hydroxylamine reacts as a nucleophile in this step. [1]

III. In a batch process 200 kg of cyclohexanone oxime was converted to

Explain why, if there is 100 % conversion of the oxime to caprolactam, exactly

15 © WJEC CBAC Ltd. (A410U20-1) Turn over.

16 © WJEC CBAC Ltd. (A410U20-1)

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(d) Cyclohexene can be produced in the laboratory by the dehydration of cyclohexanol.

boiling temperature boiling temperature

In an experiment cyclohexene was produced using the apparatus below.

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(ii) Compound L reacts with hydrogen to give a saturated ketone, compound M.

I. Suggest the type of reaction mechanism occurring in this hydrogenation. [1]

II. The 1H NMR spectrum of ketone M suggested that it was

(a) State the empirical formula of methylcyclohexane. [1]

Calculate the percentage of methylcyclohexane in the mixture. [1]

Suggest a reagent(s) that can be used for this reduction. [1]

I. State the name of this piece of apparatus. [1]

(i) Write the displayed formula for cysteine. [1]

Suggest a skeletal formula for this salt. [1]

Draw the 3D structures of these two forms. [1]

Calculate the frequency of this absorption at 480 nm. [2]

Complete the equation for this reaction. [1]

Suggest why hydroxylamine reacts as a nucleophile in this step. [1]

I. Suggest the type of reaction mechanism occurring in this hydrogenation. [1]

I. State one advantage of method 1 compared to method 2. [1]

II. State one disadvantage of method 1 compared to method 2. [1]

Write the formula of this compound. [1]

Explain why these spots now appear coloured. [2]

Suggest the formula of the organic compound that is produced. [1]

(ii) Explain why 1,3-diphenylpropene can exist as E-Z isomers. [1]

II. State the type of reaction occurring in stage 2. [1]

You must show your working. [2]

Calculate the atom economy of this reaction to make hexamine. [2]

Suggest why these signals are single peaks. [1]

Explain the meaning of these two terms in this context. [2]

(i) Calculate the percentage of chlorine in this mixture. [2]

Give the equation for this reaction. [2]