Page 1

1 (a) Complete the table using ticks () to indicate whether the sign of each type of energy change,
under standard conditions, is always positive, always negative or could be either positive or
negative.

always always either positive

energy change
positive negative or negative

electron affinity

enthalpy change of atomisation

ionisation energy

lattice energy
[2]

(b) The Born-Haber cycle for magnesium chloride is shown.

Mg2+(g) + 2Cl (g) + 2e–

ΔH5
ΔH4
Mg2+(g) + 2Cl –(g)
Mg+(g) + 2Cl (g) + e–

ΔH3
Mg(g) + 2Cl (g)

ΔH2
Mg(g) + Cl 2(g) ∆H6

ΔH1
Mg(s) + Cl 2(g)

ΔH7
MgCl 2(s)

(i) Explain why ΔH4 is greater than ΔH3.

..............................................................................................................................................

........................................................................................................................................ [1]

(ii) What names are given to the enthalpy changes ΔH6 and ΔH7?

ΔH6 .......................................................................................................................................

ΔH7 .......................................................................................................................................
[1]
 Page 2

(c) Chlorine is in Group 17.

Suggest the trend in the first electron affinity of the elements in Group 17. Explain your answer.

.....................................................................................................................................................

.....................................................................................................................................................

............................................................................................................................................... [2]

(d) The equation for the formation of magnesium oxide from its elements is shown.
1
Mg(s) + 2 O2(g) MgO(s) ΔH o = – 602 kJ mol–1

substance S o / J K–1 mol–1
Mg(s) 32.7
O2(g) 205
MgO(s) 26.9

Use the equation and the data given in the table to calculate ΔG o for the reaction at 25 °C.

ΔG o = .............................. units ..............................

[4]

[Total: 10]
 Page 3

2 (a) Compound H can be synthesised from benzene as shown.

step 1

step 2
Cl 2(g)

step 3

NH2
compound H
intermediate G

(i) State the reagents and conditions needed for step 1.

reagents ...............................................................................................................................

conditions ............................................................................................................................
[2]

(ii) Step 2 takes place in the presence of chlorine gas.

State the conditions for this reaction.

........................................................................................................................................ [1]

(iii) Draw the structure of intermediate G in the box. [1]

(iv) State the reagents and conditions needed for step 3.

reagents ...............................................................................................................................

conditions ............................................................................................................................
[2]

(b) Write an equation to show how compound H, C10H13NH2, behaves as a base.

............................................................................................................................................... [1]

(c) C
 ompare the relative basicities of ammonia, phenylamine and compound H. Explain your
answer.

.....................................................................................................................................................

.....................................................................................................................................................

............................................................................................................................................... [2]

[Total: 9]
 Page 4

3 The root of the ginger plant contains compounds with medicinal and flavouring properties. Three of
the more important compounds are gingerol, shogaol and zingerone.

(a) The structure of gingerol is shown. The CH3O– group in gingerol is unreactive.

O OH

HO
CH3O
gingerol

Gingerol reacts with acidified potassium dichromate(VI).

State the type of reaction and the functional group change which occurs during this reaction.

type of reaction ...........................................................................................................................

functional group change

from ................................................................... to ...................................................................

[1]

(b) The structure of shogaol is shown.

HO
CH3O
shogaol

(i) State the type of reaction needed to convert gingerol into shogaol.

........................................................................................................................................ [1]

(ii) State the reagents and conditions needed to convert gingerol into shogaol.

reagents ...............................................................................................................................

conditions ............................................................................................................................
[1]
 Page 5

 hogaol reacts with hot, concentrated acidified manganate(VII) ions to form two organic
(iii) S
products, Q and R.

Draw the structures of Q and R.

Q R
[2]

(c) Zingerone is formed from gingerol.

Some reactions of zingerone are shown.

Complete the table to identify the functional groups in zingerone.

functional group in zingerone

reagent and conditions observation
indicated by the observation

benzenediazonium chloride,
red ppt.
5 °C, alkaline solution

2,4-dinitrophenylhydrazine orange ppt.

warm with Tollens’ reagent no change

[2]

[Total: 7]
 Page 6

4 (a) (i) Complete the equations to show the two types of polymerisation. Draw one repeat unit for
each polymer. Include any other products.

● addition polymerisation

n CH2=CHCH3(g)

● condensation polymerisation

n HO2CCH2CO2H(s)
+
n HOCH2CH2OH(l)

[3]

(ii) Suggest the sign of the entropy changes, ΔS o, for each of the two types of polymerisation.
Explain your answers.

● ΔS o for addition polymerisation

..............................................................................................................................................

..............................................................................................................................................

..............................................................................................................................................

● ΔS o for condensation polymerisation

..............................................................................................................................................

..............................................................................................................................................

..............................................................................................................................................
[2]
 Page 7

(b) An amide bond forms when a carboxylic acid reacts with an amine.

(i) Complete the equation by writing the products in the box.

R–CO2H + H2N–R' +

[1]

(ii) Use your answer to (i) to work out the bonds that are broken and the bonds that are
formed during the reaction between a carboxylic acid and an amine.

●● bonds that are broken

..............................................................................................................................................

●● bonds that are formed

..............................................................................................................................................
[2]

(iii) Use bond energy values from the Data Booklet to calculate the enthalpy change, ΔH o,
when one mole of amide bonds is formed in the reaction in (i).

 ΔH o = .............................. kJ [2]

(c) Amide bonds can also be formed by reacting acyl chlorides with amines.

The enthalpy change for this process, ΔH o, is – 6.00 kJ mol–1.

Calculate the minimum entropy change, ΔS o, for this reaction to be spontaneous (feasible) at
298 K.

 ΔS o = .............................. J K–1 mol–1 [2]

 Page 8

The repeat unit of the polyamide Kevlar is shown.

H
H
N N O

(d) The monomers of Kevlar, benzene-1,4-dioic acid and 1,4-diaminobenzene, can be synthesised
as follows.

H 3C CH3 O2N NO2

reaction 1 reaction 2

HO2C CO2H H 2N NH2

benzene-1,4-dioic acid 1,4-diaminobenzene

State the reagents and conditions needed for:

(i) reaction 1

........................................................................................................................................ [1]

(ii) reaction 2

..............................................................................................................................................

........................................................................................................................................ [2]

(e) 
Kevlar is both strong and rigid.

Complete the table to identify two intermolecular forces and the groups involved which are
responsible for these properties of Kevlar.

intermolecular force group(s) involved

[2]

 [Total: 17]
 Page 9

5 Ethanedioyl dichloride, Cl COCOCl, is a useful reagent in organic synthesis. It can be made from
compound A in one step.

A O
C Cl
Cl C
O

(a) (i) Suggest the identity of compound A by drawing its structure in the box. [1]

(ii) State the reagents and conditions needed to convert A into Cl COCOCl.

........................................................................................................................................ [1]

Ethanedioyl dichloride is used in the following synthesis of compound Q. It is used in a 1 : 1

stoichiometric ratio with B in step 2.

step 1 step 3
B (C6H5Cl ) D

Cl COCOCl step 2 step 4

+ Al Cl 3
C (C8H4O2Cl 2)
NH2

step 5

E (C14H10NO2Cl )

step 6

Q
OH
H
N

Cl
 Page 10

(b) (i) Suggest the identities of the compounds B–E by drawing their structures in the boxes.[4]

(ii) State the reagents and conditions for the following steps.

step 1 ...................................................................................................................................

step 3 ...................................................................................................................................

step 4 ...................................................................................................................................

step 6 ...................................................................................................................................
[5]

If the amount of Cl COCOCl used in step 2 is decreased, another compound is formed in
step 2 with the molecular formula C14H8O2Cl 2.

(iii) Suggest the structure of this compound.

C14H8O2Cl 2

[1]

(iv) Identify all the steps in the synthesis of Q from benzene that are electrophilic substitution
reactions.

........................................................................................................................................ [1]
 Page 11

(c) Draw structures of the compounds formed when Q is treated with the following reagents.
If there is no reaction, write ‘no reaction’ in the box.

heat with Cr2O72– / H+(aq)

heat with
NaOH(aq)
Q
OH
H
N

Cl

Br2(aq)

HCl (aq)
room temperature

[4]

 [Total: 17]
 Page 12

6 Compounds F and J are shown in Fig. 4.1.

F J
O OH

OH O

H 2N O

Fig. 4.1

(a) 
F and J both contain the arene functional group.

(i) Identify the other functional groups in F and J.

F: .........................................................................................................................................

J: . ........................................................................................................................................
[2]

(ii) State the number of chiral centres in a molecule of F and in a molecule of J.

number of chiral centres in: F = ......................................... J = . .......................................

[1]

(b) A student proposes a multi-step synthesis of F from benzene, as shown in Table 4.1.

(i) C
 omplete Table 4.1 by providing relevant details of the reagents and conditions for steps 1
and 4, and the structure of product D.

Table 4.1

step organic reactant reagent(s) and conditions organic product

1
.........................................

D
concentrated HNO3 and
2
concentrated H2SO4

E
COOH
hot alkaline KMnO4
3 D
then dilute H2SO4
O2N
F
COOH
COOH
4
O2N ......................................... H 2N
[3]
 Page 13

(ii) In a second multi-step synthesis, the student changes the order in which the reagents and
conditions are used.
The reaction scheme is shown in Fig. 4.2.
 G is the major product of this synthesis.

concentrated
HNO3 and
hot alkaline COOH concentrated
step 1 KMnO4 H2SO4
G
then dilute
H2SO4

Fig. 4.2

Draw the structure of G.

Explain why G is the major product of the synthesis rather than E.

. ............................................................................................................................................

. ............................................................................................................................................

. ............................................................................................................................................
[2]
 Page 14

(c) 
J reacts under suitable conditions with NaOH(aq).
After acidification of the reaction mixture, compounds K and L form.

J K
OH OH

O 1. NaOH(aq) OH + L
2. HCl (aq)
O O

(i) Give the molecular formula of L.

. ...................................................................................................................................... [1]

(ii) State the two types of reaction that occur when J reacts with NaOH(aq).

1 . .........................................................................................................................................

2 . .........................................................................................................................................
[2]

(d) 
K can also be synthesised from phenol, C6H5OH.

Fig. 4.4 shows several reactions of phenol.

M
reaction 1

phenol Na(s)
OH

reaction 2

reaction 3 excess Br2(aq)

N
NaOH(aq) followed
by CO2(g) and H2SO4

K
OH

OH

O
 Page 15

(i) Write an equation for the formation of M in reaction 1.

. ...................................................................................................................................... [1]

(ii) Draw N, the product of reaction 2.

[1]

(iii) Explain why phenol is a weaker acid than K.

. ............................................................................................................................................

. ............................................................................................................................................

. ............................................................................................................................................

. ...................................................................................................................................... [2]

(e) Phenol and benzene both react with nitric acid, as shown in Fig. 4.5.

OH OH
dilute HNO3

NO2

concentrated HNO3
concentrated H2SO4
NO2

Explain why the reagents and conditions for these two reactions are different.

....................................................................................................................................................

....................................................................................................................................................

....................................................................................................................................................

....................................................................................................................................................

.............................................................................................................................................. [3]

 [Total: 18]
 Page 16

7 (a) (i) Define first electron affinity.

..............................................................................................................................................

..............................................................................................................................................

........................................................................................................................................ [2]

(ii) T
 he first electron affinity of an atom is usually an exothermic process, whereas the second
electron affinity is an endothermic process.

Suggest why.

..............................................................................................................................................

........................................................................................................................................ [1]

(iii) Describe the general trend in first electron affinities for Cl, Br and I. Explain your answer.

..............................................................................................................................................

..............................................................................................................................................

........................................................................................................................................ [2]

(b) Table 3.1 shows energy changes to be used in this question and in (c).

Table 3.1

energy change value / kJ mol–1

standard enthalpy change of atomisation of zinc +131
first ionisation energy of zinc +906
second ionisation energy of zinc +1733
standard enthalpy change of formation of ZnI2(s) –208
lattice energy, , of zinc iodide, ZnI2(s) –2605
first ionisation energy of iodine +1008
second ionisation energy of iodine +1846
I–I bond energy +151
enthalpy change of sublimation of iodine, I2(s) → I2(g) +62
 Page 17

Calculate the first electron affinity for iodine. Use relevant data from Table 3.1 in your working.
It may be helpful to draw a labelled energy cycle.
Show all working.

 first electron affinity for iodine = .............................. kJ mol–1 [3]

(c) Predict how of CdI2(s) differs from of ZnI2(s).

Place a tick (✓) in the appropriate box in Table 3.2.

of CdI2(s) is less of CdI2(s) is the of CdI2(s) is more

negative than of ZnI2(s) same as of ZnI2(s) negative than of ZnI2(s)

Explain your answer.

.....................................................................................................................................................

............................................................................................................................................... [1]

 [Total: 9]
 Page 18

8 (a) Compare the relative acidities of ethanol, ethanoic acid, chloroethanoic acid and phenol.
Explain your reasoning.

.................................. > .................................. > .................................. > ..................................

most acidic least acidic

.....................................................................................................................................................

.....................................................................................................................................................

.....................................................................................................................................................

.....................................................................................................................................................

.....................................................................................................................................................

....................................................................................................................................................
[5]

(b) An excess of ethanedioic acid, HOOCCOOH(aq), is reacted with warm acidified KMnO4(aq).

State the type of reaction undergone by ethanedioic acid.

Describe what you would observe.
Write an equation for this reaction.

Your equation can use [O] or [H] as necessary.

type of reaction ...........................................................................................................................

observations ...............................................................................................................................

equation ......................................................................................................................................
[3]
 Page 19

(c) A section of a polyester is shown.

polyester
O O O O

O CH2 C O CH C O CH2 C O CH C

CH3 CH3

Fig. 8.1

Draw the structures of the two monomers that form this polyester.

[2]

(d) S
 erine can polymerise to form two different types of condensation polymer; a polyester and a
polypeptide.

serine
OH
H2C O
H2N C C

H OH

Fig. 8.2

Draw the structure of the polypeptide showing two repeat units. The peptide linkage should be
shown displayed.

[2]

(e) Explain why condensation polymers normally biodegrade more readily than addition polymers.

.....................................................................................................................................................

............................................................................................................................................... [1]

[Total: 13]
 Page 20

Important values, constants and standards

molar gas constant R = 8.31 J K–1 mol–1

Faraday constant F = 9.65 × 104 C mol–1
Avogadro constant L = 6.022 × 1023 mol–1
electronic charge e = –1.60 × 10–19 C
molar volume of gas Vm = 22.4 dm3 mol–1 at s.t.p. (101 kPa and 273 K)
Vm = 24.0 dm3 mol–1 at room conditions
ionic product of water Kw = 1.00 × 10–14 mol2 dm–6 (at 298 K (25 °C))
specific heat capacity of water c = 4.18 kJ kg–1 K–1 (4.18 J g–1 K–1)
 The Periodic Table of Elements
Group
1 2 13 14 15 16 17 18
1 2

H He
hydrogen helium
Key 1.0 4.0
3 4 atomic number 5 6 7 8 9 10

Li Be atomic symbol B C N O F Ne
lithium beryllium name boron carbon nitrogen oxygen fluorine neon
6.9 9.0 relative atomic mass 10.8 12.0 14.0 16.0 19.0 20.2
11 12 13 14 15 16 17 18
Na Mg Al Si P S Cl Ar
sodium magnesium aluminium silicon phosphorus sulfur chlorine argon
23.0 24.3 3 4 5 6 7 8 9 10 11 12 27.0 28.1 31.0 32.1 35.5 39.9
19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36
K Ca Sc Ti V Cr Mn Fe Co Ni Cu Zn Ga Ge As Se Br Kr
potassium calcium scandium titanium vanadium chromium manganese iron cobalt nickel copper zinc gallium germanium arsenic selenium bromine krypton
39.1 40.1 45.0 47.9 50.9 52.0 54.9 55.8 58.9 58.7 63.5 65.4 69.7 72.6 74.9 79.0 79.9 83.8
37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54
Rb Sr Y Zr Nb Mo Tc Ru Rh Pd Ag Cd In Sn Sb Te I Xe
rubidium strontium yttrium zirconium niobium molybdenum technetium ruthenium rhodium palladium silver cadmium indium tin antimony tellurium iodine xenon
85.5 87.6 88.9 91.2 92.9 95.9 – 101.1 102.9 106.4 107.9 112.4 114.8 118.7 121.8 127.6 126.9 131.3
55 56 57–71 72 73 74 75 76 77 78 79 80 81 82 83 84 85 86
lanthanoids
Cs Ba Hf Ta W Re Os Ir Pt Au Hg Tl Pb Bi Po At Rn
caesium barium hafnium tantalum tungsten rhenium osmium iridium platinum gold mercury thallium lead bismuth polonium astatine radon
132.9 137.3 178.5 180.9 183.8 186.2 190.2 192.2 195.1 197.0 200.6 204.4 207.2 209.0 – – –
87 88 89–103 104 105 106 107 108 109 110 111 112 113 114 115 116 117 118
actinoids
Fr Ra Rf Db Sg Bh Hs Mt Ds Rg Cn Nh Fl Mc Lv Ts Og
francium radium rutherfordium dubnium seaborgium bohrium hassium meitnerium darmstadtium roentgenium copernicium nihonium flerovium moscovium livermorium tennessine oganesson
– – – – – – – – – – – – – – – – –

57 58 59 60 61 62 63 64 65 66 67 68 69 70 71
lanthanoids La Ce Pr Nd Pm Sm Eu Gd Tb Dy Ho Er Tm Yb Lu
lanthanum cerium praseodymium neodymium promethium samarium europium gadolinium terbium dysprosium holmium erbium thulium ytterbium lutetium
138.9 140.1 140.9 144.4 – 150.4 152.0 157.3 158.9 162.5 164.9 167.3 168.9 173.1 175.0
89 90 91 92 93 94 95 96 97 98 99 100 101 102 103
actinoids Ac Th Pa U Np Pu Am Cm Bk Cf Es Fm Md No Lr
actinium thorium protactinium uranium neptunium plutonium americium curium berkelium californium einsteinium fermium mendelevium nobelium lawrencium
– 232.0 231.0 238.0 – – – – – – – – – – –
Page 21