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WCH05 01 Que 20180119
WCH05 01 Que 20180119
Chemistry
Advanced
Unit 5: General Principles of Chemistry II – Transition
Metals and Organic Nitrogen Chemistry
(including synoptic assessment)
Friday 19 January 2018 – Morning Paper Reference
Instructions
• Use black ink or black 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.
• –Theusemarks for each question are shown in brackets
this as a guide 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
• Try
Read each question carefully before you start to answer it.
• Checkto answer every question.
• Show allyouryouranswers if you have time at the end.
• working in calculations and include units where appropriate.
Turn over
P51947A
©2018 Pearson Education Ltd.
6/5/5/5/1/
*P51947A0132*
SECTION A
Answer ALL the questions in this section. You should aim to spend no more than 20 minutes on
1 Which electrode and solution would be used to measure the standard electrode potential
of the manganese(III)/manganese(II) half-cell?
3+ 2+
Mn (aq) + e– U Mn (aq)
Electrode Solution
–3 3+
A manganese 1 mol dm Mn (aq)
–3 3+ 2+
B manganese 1 mol dm with respect to Mn (aq) and Mn (aq)
–3 3+
C platinum 1 mol dm Mn (aq)
–3 3+ 2+
2 In which pair of species are the oxidation numbers of the d-block elements the same?
2+
A [Cr(NH3)4Cl2]+ and [Mn(H2O)6]
B CrO42– and TiCl3
C Cr2O3 and [Fe(CN)6]3–
D Cr2O72– and MnO4–
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3 One mole of metal ions reacted in solution with one mole of sulfur dioxide.
The half-equation for the sulfur dioxide reaction is
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The original oxidation number of the metal was +3. What was the oxidation number
of the metal after the reaction?
A +1
B +2
C +4
D +5
(1)
A [CrCl4]–
B [CuCl2]–
C [Pt(NH3)2Cl2]
D [TiCl6]2–
3
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5 An ion of metal M has a charge of +n. It forms a complex ion with a charged
bidentate ligand, L.
(b) Another complex ion can be formed in which both of the bidentate ligands L,
in [ML2](+n – 4), are replaced by the neutral monodentate ligand Z.
What is the formula of the complex ion?
(1)
A [MZ2]n+
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6 Two reactions of copper(II) sulfate solution are shown.
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copper(II) sulfate
solution
potassium iodide
zinc solution
D Zinc sulfate
7 When benzene reacts with a mixture of concentrated nitric and sulfuric acids,
the reaction is
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A electrophilic addition.
B electrophilic substitution.
C nucleophilic addition.
D nucleophilic substitution.
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8 Benzene and phenol react with bromine.
(a) What is the organic product when benzene reacts with excess bromine in the
Br
Br
Br Br
Br
Br
Br
Br Br
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Br Br
Br
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(b) Bromine reacts more readily with phenol than with benzene. This is because the
(1)
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9 The structure of compound G is
CH3
NH2
CH3 CH3
+ +
NH2(C2H5) N(C2H5)3
A B
NH2(C2H5) N(C2H5)3
+ +
CH3 CH3
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CONHCH3 NHCOCH3
C D
CONHCH3 NHCOCH3
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10 Four different compounds, P, Q, R and S, are structural isomers with molecular formula C9H10O2.
O
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O
O
compound P compound Q
OH
OH
O
compound R compound S
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(a) Which compound does not exhibit optical isomerism but does react with
sodium hydrogencarbonate to give a colourless gas?
(1)
A Compound P
B Compound Q
C Compound R
D Compound S
B Compound Q
C Compound R
D Compound S
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11 A reaction sequence is shown.
Step 1 Step 2 OH
Step 3
H
N Step 4 Cl
O O
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(d) Which is the reagent for Step 4?
(1)
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A CH3CH2CH2CH2NH2
B CH3CH(NH2)CH2CH3
C CH3CH2CH2CONH2
D CH3CH(CONH2)CH3
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SECTION B
Answer ALL the questions. Write your answers in the spaces provided.
(ii) Aluminium only forms compounds in which its oxidation number is +3,
whereas iron has compounds with a variety of oxidation numbers.
Suggest a reason why iron forms stable compounds with more than one
*(b) Most aluminium compounds are colourless but iron(III) compounds are coloured.
3+
Explain why [Fe(H2O)6] ions are coloured.
(4)
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*P51947A01232*
(c) Aluminium ions and iron(III) ions form complexes in solution.
These solutions are acidic.
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3+
(i) Draw the structure of the [Fe(H2O)6] complex ion, showing clearly the shape
3+ 3+
around the Fe ion, and which atoms in the ligands are attached to the Fe ion.
(2)
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(d) Aluminium chloride, AlCl3, and iron(III) chloride, FeCl3, can both be used as catalysts
in Friedel-Crafts reactions.
–
Suggest, by reference to the electronic structure of AlCl3 , how the AlCl4 ion forms.
(2)
–
(ii) Draw a dot-and-cross diagram of the thiocyanate ion, [SCN] .
Hence suggest a structure of the ion, showing all the bonds and which atom
has the negative charge.
(2)
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*P51947A01432*
3+
(iii) Suggest two ways in which the thiocyanate ion could bond to the Fe in the complex.
(1)
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13 This question is about carboxylic acids.
(a) An organic compound, T, contains the elements carbon, hydrogen and oxygen only.
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(ii) The mass spectrum of compound T has a peak at m/e = 45.
Give the displayed formulae of two species that could produce this peak.
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(2)
(iii) The low resolution proton nmr spectrum of compound T has four peaks with
areas in the ratio 1 : 2 : 2 : 1.
Draw the structure of compound T and explain how your structure is
consistent with the proton nmr data.
(3)
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(b) The structure of 2-hydroxy-2-phenylpropanoic acid is shown.
CH3 O
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*P51947A01832*
(ii) Poly(2-hydroxy-2-phenylpropanoic acid) is a possible biodegradable polymer.
Draw a section of this polymer, showing two repeat units.
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(2)
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14 This question is about redox reactions.
(a) Vanadium exists in different oxidation states which can be interconverted using
Half-equation E 9/ V
2+
Zn (aq) + 2e– U Zn(s) –0.76
3+ 2+
V (aq) + e– U V (aq) –0.26
(ii) Select, from the table, a reducing agent which should reduce vanadium(V) to
vanadium(IV) but not to vanadium(III). Justify your answer.
(3)
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*P51947A02032*
3+ 2+ 2+
(iii) Write the balanced equation for the disproportionation of V into V and VO
and explain whether this reaction is feasible under standard conditions.
State symbols are not required.
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(3)
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(b) Excess potassium iodide solution was added to 25.0 cm3 of an aqueous solution of
bromine.
The iodine produced was titrated with sodium thiosulfate solution. All of the iodine
–3
required 24.20 cm3 of 0.100 mol dm sodium thiosulfate solution for reaction.
2S2O32– + I2 o S4O62– + 2I
–
22
*P51947A02232*
(ii) In another experiment, 100.0 cm3 of the same aqueous solution of bromine
was treated directly with 0.00100 moles of sodium thiosulfate.
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*P51947A02332* Turn over
SECTION C
15
Sweeteners
Table sugar (sucrose) contributes to tooth decay and obesity, so some manufacturers add
other natural or artificial sweeteners to food.
Honey is a natural sweetener and has about the same relative sweetness as sucrose.
The sweetness arises from the simple sugars glucose and fructose. Honey also contains
pinocembrin which is an antioxidant.
HO O
OH O
Saccharin is an artificial sweetener, which was first produced in 1879. It is over 300 times
sweeter than sucrose.
O
C
saccharin
NH
S
O
O
Aspartame is an ester of the dipeptide formed from the amino acids phenylalanine and
aspartic acid. It was first produced in 1965 and is about 200 times sweeter than sucrose.
O
NH2
H
N
OH
aspartame
O O
O
24
*P51947A02432*
(a) (i) Give the molecular formula for pinocembrin.
(1)
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(ii) Label the chiral carbon atom in pinocembrin with an asterisk (*).
(1)
HO O
OH O
(b) One route for the synthesis of saccharin starts with the reaction between
methylbenzene and chlorosulfonic acid, HSO3Cl.
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CH3 CH3
SO2Cl
HSO3Cl
25
*P51947A02532* Turn over
(c) Another route for the synthesis of saccharin starts with the reaction between
methyl 2-aminobenzoate and nitrous acid (prepared from sodium nitrite and
hydrochloric acid).
C CH3 C CH3
HNO2 SO2
O Intermediate A O
Step 1 Step 2
NH2 SO2H
Step 3 Cl2
O O
O
C C CH3 C CH3
catalyst O Reagent B O
NH
Step 5 Step 4
C CH3 C
O
NH + ..................................................
SO2NH2 S
O
O
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*P51947A02632*
(iv) The sodium salt of saccharin is much more soluble in water than saccharin.
O
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C
saccharin
NH
S
O
O
The acidic hydrogen is the one that is attached to the nitrogen atom.
Complete the structure of the sodium salt of saccharin, showing the charges
on both ions.
(1)
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*P51947A02732* Turn over
(d) Phenylalanine and aspartic acid are amino acids.
HO
OH OH
NH2 O NH2
(i) Draw the structure of the organic compound formed when hydrochloric acid
is added to phenylalanine.
(1)
28
*P51947A02832*
(iii) The structure of aspartame is
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O
NH2
H
N
OH
O O
O
aspartame
Draw the structure of the dipeptide formed between phenylalanine and
aspartic acid that is required to form aspartame.
(2)
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(iv) Identify, by name or formula, the alcohol needed to form aspartame from the
dipeptide in (d)(iii).
(1)
29
*P51947A02932* Turn over
(e) Sugar alcohols, such as sorbitol, are also used as artificial sweeteners.
Sorbitol is made from glucose.
HO HO
O OH
OH OH OH OH
glucose sorbitol
(ii) Describe a chemical test which will distinguish between glucose and sorbitol.
Give the result for each substance.
(3)
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*P51947A03032*
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*P51947A03132*
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*P51947A03232*
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