Chemistry: Pearson Edexcel GCE

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Pearson
Edexcel GCE
Chemistry
Advanced
Unit 5: General Principles of Chemistry II – Transition
Metals and Organic Nitrogen Chemistry
(including synoptic assessment)
Wednesday 22 June 2016 – Morning Paper Reference
Time: 1 hour 40 minutes 6CH05/01

You must have: Data Booklet Total Marks
Candidates may use a calculator.
Instructions
• Use black ink or ball-point pen.
• centre
Fill in the boxes at the top of this page with your name,
number and candidate number.
• Answer allthequestions.
Answer
• – there may bequestions in the spaces provided
more space than you need.
Information
• The total mark for this paper is 90.
• – use this asfora guide
The marks each question are shown in brackets
as to how much time to spend on each question.
• written
Questions labelled with an asterisk (*) are ones where the quality of your
communication will be assessed
– you should take particular care with your spelling, punctuation and grammar, as
well as the clarity of expression, on these questions.
• A Periodic Table is printed on the back cover of this paper.
Advice
• Keep
Read each question carefully before you start to answer it.
• Try toananswer
eye on the time.
• Check your answers
every question.
• if you have time at the end.
Turn over
P46661A
©2016 Pearson Education Ltd.
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3/6/6/3/5/5/e2
SECTION A
Answer ALL the questions in this section. You should aim to spend no more than 20 minutes on
DO NOT WRITE IN THIS AREA

this section. For each question, select one answer from A to D and put a cross in the box .
If you change your mind, put a line through the box and then mark your new answer with a
cross .
1 Which of the following gives the oxidation states of manganese in the ions shown?
MnO42− MnO3–
A +7 +6
B +6 +5
C +7 +5

D +6 +6
(Total for Question 1 = 1 mark)
2 Which of the following gives the electrodes and electrolyte that are used in an
alkaline hydrogen fuel cell?
Electrodes Electrolyte
A graphite potassium hydroxide solution
B graphite water with a little salt

C platinum potassium hydroxide solution
D platinum water with a little salt
2
*P46661A0232*
3 Which of the following cannot be used to detect alcohol in a breathalyser test?
A Fractional distillation
B Fuel cell
C Infrared spectroscopy
D Reduction of dichromate(VI) ions

4 A titration using potassium manganate(VII) in dilute sulfuric acid can be used to

determine the percentage of
A aspirin in aspirin tablets.
B chlorine in bleach.
C copper in an alloy.
D iron(II) sulfate in iron tablets.

5 Which of the following gives the electronic configurations for a chromium atom and
a chromium(II) ion?
Cr Cr2+
A [Ar]3d44s2 [Ar]3d4
B [Ar]3d54s1 [Ar]3d4
C [Ar]3d44s2 [Ar]3d24s2
D [Ar]3d54s1 [Ar]3d34s1
3
*P46661A0332* Turn over
6 Aqueous sodium hydroxide and aqueous ammonia are added to separate solutions
of the same metal ion. The observations are shown in the table below.

Reagent added A few drops Excess
NaOH(aq) green precipitate green precipitate remains
green precipitate dissolves

NH3(aq) green precipitate
to form a blue solution
The metal ion is
A Cr3+(aq).
B Fe2+(aq).
C Fe3+(aq).
D Ni2+(aq).

7 The reaction between cerium(IV) ions and thallium(I) ions is very slow.
2Ce4+(aq) + Tl +(aq) o 2Ce3+(aq) + Tl 3+(aq)
Which of these ions could catalyse this reaction?
A Al 3+
B Fe3+
C Na+
D Zn2+
8 Which of these hydroxides is amphoteric?
A Cu(OH)2
B Mg(OH)2
C Ni(OH)2
D Zn(OH)2
4
*P46661A0432*
9 During a titration between acidified manganate(VII) ions and sulfate(IV) ions, the
manganate(VII) ions are reduced to manganese(II) ions and the sulfate(IV) ions are
oxidized to sulfate(VI) ions.
The mole ratio of manganate(VII) ions to sulfate(IV) ions in this reaction is
A 5:2
B 7:4
C 2:5
D 4:7
10 The total number of compounds with the structural formula C6H3CH3(NO2)2, which
contain a benzene ring, is
A four.
B five.
C six.
D seven.
Use this space for any rough working. Anything you write in this space will gain no credit.
5
11 This question is about the ester shown below.
CH3 O

CH3 CH O C CH2 CH3
(a) The number of peaks seen in the low resolution proton nmr spectrum of this
ester is
(1)
A two.
B three.
C four.
D five.
(b) The peak in the high resolution proton nmr spectrum corresponding to the
proton in bold on the structure above will
(1)

A not be split.
B be split into three peaks.
C be split into four peaks.
D be split into seven peaks.

(Total for Question 11 = 2 marks)
6
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12 Safranal is one of the substances that contributes to the aroma of saffron.
Separate samples of safranal were tested with bromine water,

2,4-dinitrophenylhydrazine and Fehling’s solution.
What are the final observations when safranal is tested with each of those reagents?
Bromine water 2,4-dinitrophenylhydrazine Fehling’s solution
A orange solution orange solution red precipitate
colourless
B orange precipitate red precipitate

solution
C orange solution orange solution blue solution
colourless
D orange precipitate blue solution
solution

7
13 The structure of the organic product of the reaction between phenol and excess
bromine water is

Br
A
OH
Br
OH

C
Br Br
OH
Br Br
D
Br

8
*P46661A0832*
14 If it is assumed that the structure of benzene has three localised double bonds
(structure X), the calculated standard enthalpy change of hydrogenation
is −360 kJ mol–1.
+ 3H2
structure X
The actual standard enthalpy change of hydrogenation of benzene is −208 kJ mol–1.
From these data, it can be deduced that the

A actual benzene structure is kinetically more stable than structure X as it
requires a high activation energy to react.
B actual benzene structure is thermodynamically more stable than structure X
as it has a lower enthalpy content.
C structure X is kinetically unstable as it undergoes addition reactions at room
temperature.
D structure X is thermodynamically more stable than the actual benzene
structure as the standard enthalpy change of hydrogenation is more
exothermic.
9
15 The repeat unit for poly(propenamide) is

⎡ H H H O ⎡
⎢ ⎢
A ⎢ N C C C ⎢
⎢ ⎢
⎢ ⎢
⎣ H H ⎣
⎡ H H H O ⎡
⎢ ⎢
⎢ ⎢
⎢ ⎢
B ⎢ N C C C ⎢
⎣ ⎣
⎡ H H ⎡
C
⎢ C C ⎢
⎢ ⎢
⎢ H C O⎢
⎢ ⎢
⎣ NH2 ⎣

⎡ H ⎡
D ⎢ C C
⎢
⎢ ⎢
⎢ C O⎢
⎢ ⎢
⎣ NH2 ⎣

10
*P46661A01032*
16 The structures of three amino acids are shown in the table.
Amino acid Structure

cysteine HSCH2CH(NH2)COOH
glycine H2NCH2COOH
threonine CH3CH(OH)CH(NH2)COOH
The tripeptide glycine-cysteine-threonine is
A H2NCH2CONHCH(CH(OH)CH3)CONHCH(CH2SH)COOH
B H2NCH2CONHCH(CH2SH)CONHCH(CH(OH)CH3)COOH
C H2NCH(CH(OH)CH3)CONHCH(CH3SH)CONHCH2COOH
D H2NCH(CH2SH)CONHCH2 CONHCH(CH(OH)CH3)COOH
17 The amino acid alanine, H2NCH(CH3)COOH, exists as a solid at room temperature.
The most important reason for this is that it
A exists as a zwitterion.
B forms hydrogen bonds.
C is amphoteric.
D has strong London forces.

18 Complete combustion of a hydrocarbon produced 0.66 g of carbon dioxide and

0.225 g of water.
Which of the following molecular formulae is consistent with these data?
A C3H6.
B C3H8.
C C6H6.
D C6H10.
11
19 Phenol can be produced from benzene as shown in the reaction sequence below.

SO3H OH
Step 1 Step 2
yield 80% yield 90%
benzene phenol
Mr = 78 Mr = 94
The mass of phenol, to 2 decimal places, produced from 3.90 g of benzene is

A 3.38 g.
B 3.76 g.
C 4.23 g.
D 4.70 g.

TOTAL FOR SECTION A = 20 MARKS
12
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BLANK PAGE
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13
Turn over
SECTION B
Answer ALL the questions. Write your answers in the spaces provided.

20 Vanadium exists in different oxidation states which can be interconverted using
suitable oxidising and reducing agents.
(a) Use relevant standard electrode potential values, on page 14 of the Data Booklet,
9
to complete the table below in which two E values are missing.
(1)
9
Half-equation E /V
V2+(aq) + 2e− U V(s)
V3+(aq) + e− U V2+(aq)

VO2+(aq) + 2H+(aq) + e− U V3+(aq) + H2O(l) +0.34
I2(aq) + 2e− U 2I−(aq) +0.54
VO2+(aq) + 2H+(aq) + e− U VO2+(aq) + H2O(l) +1.00
14
*P46661A01432*
(b) The standard electrode potential of V3+(aq) + e− U V2+(aq) is measured using the
apparatus below.
V
hydrogen gas
B
platinum electrode A
solution
containing H+(aq) C
(i) Identify, by name or formula, the substances needed in the salt bridge and the
right-hand half-cell to measure the standard electrode potential.
(3)
A Salt bridge containing a solution of

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B Electrode made of
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C Solution containing
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(ii) State the three standard conditions needed for this measurement.
(2)
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15
*(c) A solution containing iodide ions, I−, was added to an acidified solution
containing vanadium(V) ions, VO2+.

Predict the oxidation state of the vanadium ions left at the end of the reaction.
9
Justify your prediction by calculating the Ecell for any relevant reaction(s).
Write the ionic equation for any reaction(s) occurring. State symbols are not required.
(5)
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16
*P46661A01632*
21 (a) The structures of 2-aminopropanoic acid and 3-aminopropanoic acid are shown.
H H H H
O O
H C C C H2 N C C C
OH OH
H NH2 H H
2-aminopropanoic acid 3-aminopropanoic acid
(i) Explain how the low resolution proton nmr spectra of these two amino acids differ.
(2)
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(ii) Explain whether or not 3-aminopropanoic acid is chiral.

(1)
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(iii) Write ionic equations for the reaction of 3-aminopropanoic acid with
(2)
H+ ions
OH– ions
17
(iv) Draw two repeat units of the polymer formed when 3-aminopropanoic acid
polymerizes.
(1)

(b) The food colouring E110 is also known as Sunset Yellow.

It can be synthesised as shown below.
+
NH2 N N Cl −
Step 1
NaO3S NaO3S
Step 2
HO
N N DO NOT WRITE IN THIS AREA
SO3Na
NaO3S
Sunset Yellow
(i) Give the reagents and condition for Step 1.

(2)
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18
*P46661A01832*
(ii) Draw the structure of the reagent needed for Step 2.
(1)
(iii) Explain why Sunset Yellow can exist as geometric isomers.

(1)
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*(iv) Describe the essential steps of the method that you would use to prepare
a pure, dry sample of the solid Sunset Yellow from an impure sample of the
food colouring. You may assume that ethanol is a suitable solvent for this
method.
(4)
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19
(v) Suggest how you could check that a sample of Sunset Yellow is pure.
(1)

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(c) Explain how a chemist could use phenylmethanol to synthesise a sample of

benzamide in three steps.
O
CH2OH C
NH2
phenylmethanol benzamide
Include the reagents for the steps in the synthesis and draw the structures of all
the intermediates.

(5)
20
*P46661A02032*
22 Copper and zinc are both in the d-block of the Periodic Table. Copper forms
compounds that contain Cu+ and Cu2+ ions but zinc only forms compounds that
contain Zn2+ ions.
(a) Complete the electronic configurations of the Cu2+ ions and Zn2+ ions and hence
explain why copper is classified as a transition metal but zinc is not.
(2)
Cu2+ [Ar] ............... . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . .
Zn2+ [Ar] ............... . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . .
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(b) Some photochromic glasses contain silver(I) and copper(I) chlorides.
Explain, with the aid of an equation, why these photochromic glasses go darker in
sunlight.
(2)
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21
(c) Copper forms a complex ion with the formula [CuCl 4]2−. This has the same shape
as [Pt(NH3)2Cl 2].

Draw the shape of the [CuCl 4]2− ion and state the type of bonding between the
ligands and the metal ion.
(2)
Shape
Bonding..... . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................
(d) The [CuCl 2]− ion is formed by boiling a solution of copper(II) chloride with copper
turnings and concentrated hydrochloric acid.
(i) Write an equation for this reaction. State symbols are not required.

(1)
(ii) State the meaning of the term disproportionation and explain whether or
not this reaction to form the [CuCl 2]− ion is a disproportionation reaction.
(2)
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22
*P46661A02232*
(iii) Explain why the [CuCl 2]− ions are colourless.
(2)
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(e) Copper(II) sulfate solution reacts with aqueous sodium hydroxide and with
aqueous ammonia.
CuSO4(aq)
aqueous sodium excess aqueous ammonia

hydroxide
copper(II) hydroxide deep blue solution

blue precipitate containing
[Cu(NH3)4(H2O)2]2+
(i) Write the ionic equation for the reaction of copper(II) sulfate solution with
aqueous sodium hydroxide. Include state symbols.
(1)
(ii) State the type of reaction occurring overall when excess aqueous ammonia is
added to copper(II) sulfate solution.
(1)
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23
(f ) 1,2-diaminoethane is a bidentate ligand. It reacts with copper(II) ions in aqueous
solution.

[Cu(H2O)6]2+ + 3H2NCH2CH2NH2 U [Cu(H2NCH2CH2NH2)3]2+ + 6H2O
(i) State what is meant by the term bidentate.

(1)
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(ii) Explain, in terms of entropy, why the reaction takes place.

(2)
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TOTAL FOR SECTION B = 47 MARKS
24
*P46661A02432*
SECTION C
Answer ALL the questions. Write your answers in the spaces provided.
23
Analgesics
Analgesics are taken to relieve the symptoms of pain.
Paracetamol
This has been synthesised in a three-step process since the 1950s.
O
HO
Ibuprofen
This was first synthesised in the 1960s from propanoic acid. That process involved six steps
and produced more waste than the required drug.
OH
It is now manufactured in a three-step process.

Some data about these two analgesics are given in the table below.
Molecular Molar mass

Analgesic
formula / g mol–1
paracetamol C8H9NO2 151
ibuprofen C13H18O2 206
25
(a) Name the functional group in paracetamol, other than the phenol group.
(1)

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(b) Paracetamol is made from phenol in a three-step process.
NO2
dilute H2SO4
+
NaNO3
HO Step 1 HO HO
NO2
4-nitrophenol 2-nitrophenol
H
NO2 NH2 N
NaBH4
O

Step 2 Step 3
HO HO HO
(i) In a typical nitration of an arene, the electrophile is formed as shown below.
HNO3 + H2SO4 l H2NO3+ + HSO4− Equation 1

...................... . . . . . . ............................ ............................ ............................
H2NO3+ l H2O + NO2+ Equation 2
Identify the acid-base conjugate pairs in Equation 1. Write your answers on

the dotted lines under the equation.
(1) DO NOT WRITE IN THIS AREA
26
*P46661A02632*
(ii) Give a mechanism for the nitration of phenol by NO2+ to form 4-nitrophenol.
(3)
(iii) Explain why phenol is nitrated much more readily than benzene.
(2)
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(iv) State the type of reaction taking place in Step 2.

(1)
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(v) Suggest a reagent for Step 3.

(1)
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27
(vi) 2-nitrophenol has a melting temperature of 46 oC and 4-nitrophenol has a
melting temperature of 114 oC.

Suggest, in terms of intermolecular forces, why these two compounds have
different melting temperatures.
(2)
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(c) Paracetamol can be hydrolysed to form 4-aminophenol and ethanoic acid.

N NH2
O + H 2O + CH3COOH
HO HO
The amount of 4-aminophenol produced can be determined using a redox

titration. The half-equation for the oxidation of 4-aminophenol is given below.
NH2 NH
+ 2H+ + 2e−
HO O
The oxidizing agent is ammonium cerium(IV) sulfate and ferroin indicator is used
to detect the end-point of the titration. During the reaction, the Ce4+ ions are
reduced to Ce3+ ions.
(i) Write the overall equation for the reaction between Ce4+ ions and
4-aminophenol.
(1)
28
*P46661A02832*
(ii) In an experiment, 0.500 g of a tablet containing paracetamol was hydrolysed
and the solution was made up to 100 cm3.
20.0 cm3 portions of the resulting solution were titrated with 0.100 mol dm–3
ammonium cerium(IV) sulfate solution.
The mean titre was 12.60 cm3.

Calculate the percentage, by mass, of paracetamol in the tablet.
(5)
29
(d) (i) Identify the chiral carbon atom in ibuprofen with an asterisk (*).
(1)

O
OH
(ii) Suggest a problem in the manufacture of a single isomer of a chiral drug

and describe a way that the pharmaceutical industry might overcome this
problem.
(2)
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. . . . . . . . . . . ..................................... . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . .
. . . . . . . . . . . ..................................... . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . .
. . . . . . . . . . . ..................................... . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . .
. . . . . . . . . . . ..................................... . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . .
(e) Ibuprofen was originally made in a six-step process but is now made in a three-step
process.
Suggest a specific environmental reason why the manufacturing process was

changed.
(1)
. . . . . . . . . . . ..................................... . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . .
. . . . . . . . . . . ..................................... . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . .
. . . . . . . . . . . ..................................... . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . .
30
*P46661A03032*
(f ) Ibuprofen is not very soluble in water. It can be made into an ionic, soluble salt by
reacting it with lysine.
O
O
OH
OH
NH2 NH2
Ibuprofen Lysine
Draw the structures of both the cation and the anion in the soluble salt formed
when ibuprofen reacts with lysine.
(2)

TOTAL FOR SECTION C = 23 MARKS

TOTAL FOR PAPER = 90 MARKS
31
*P46661A03132*
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*P46661A03232*
32

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Centre Number Candidate Number

Time: 1 hour 40 minutes 6CH05/01

Candidates may use a calculator.

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(Total for Question 1 = 1 mark)

A graphite potassium hydroxide solution

B graphite water with a little salt

C platinum potassium hydroxide solution

D platinum water with a little salt

(Total for Question 2 = 1 mark)

D Reduction of dichromate(VI) ions

4 A titration using potassium manganate(VII) in dilute sulfuric acid can be used to

A aspirin in aspirin tablets.

D iron(II) sulfate in iron tablets.

(Total for Question 5 = 1 mark)

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NaOH(aq) green precipitate green precipitate remains

green precipitate dissolves

The metal ion is

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2Ce4+(aq) + Tl +(aq) o 2Ce3+(aq) + Tl 3+(aq)

Which of these ions could catalyse this reaction?

8 Which of these hydroxides is amphoteric?

The mole ratio of manganate(VII) ions to sulfate(IV) ions in this reaction is

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B be split into three peaks.

C be split into four peaks.

D be split into seven peaks.

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Separate samples of safranal were tested with bromine water,

Bromine water 2,4-dinitrophenylhydrazine Fehling’s solution

A orange solution orange solution red precipitate

B orange precipitate red precipitate

C orange solution orange solution blue solution

(Total for Question 12 = 1 mark)

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(Total for Question 13 = 1 mark)

The actual standard enthalpy change of hydrogenation of benzene is −208 kJ mol–1.

From these data, it can be deduced that the

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(Total for Question 15 = 1 mark)

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Amino acid Structure

The tripeptide glycine-cysteine-threonine is

17 The amino acid alanine, H2NCH(CH3)COOH, exists as a solid at room temperature.

The most important reason for this is that it

B forms hydrogen bonds.

D has strong London forces.

18 Complete combustion of a hydrocarbon produced 0.66 g of carbon dioxide and

Which of the following molecular formulae is consistent with these data?

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The mass of phenol, to 2 decimal places, produced from 3.90 g of benzene is

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