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1. In colder parts of the universe, between stars, molecules have been identified.

One
such molecule is carbon monoxide, CO.

(i) The structure of carbon monoxide is represented as C O

What type of covalent bond is represented by the arrow?

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[1]

(ii) Draw a dot-cross diagram for a molecule of carbon monoxide.

C O
[3]

(iii) Another molecule found in space is OCS, which has the same shape as CO2.
OCS is not stable under the conditions on Earth. We can, however, predict the
shape of the molecule using electron pair repulsion theory. Explain this theory
and use it to predict the shape of the OCS molecule.

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[5]
[Total 9 marks]

Bishop Thomas Grant School 1


2. (i) Give the oxidation states of chlorine in Cl2 and HClO.

Cl2 …….. HClO ……..


[2]

(ii) Give the name of the process in whichCl2 is changed into HClO.

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[1]

(iii) Explain your choice of answer in (ii).

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[1]
[Total 4 marks]

3. (i) Ammonia molecules form hydrogen bonds with each other.


What features of the ammonia molecule cause it to undergo hydrogen bonding
with other ammonia molecules?

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[2]

(ii) Ammonia is very soluble in water because of the hydrogen bonds formed
between ammonia molecules and water molecules.

Draw a diagram showing an ammonia molecule hydrogen bonded to a water molecule.


Include lone pairs and partial charges (δ + and δ –).
[3]
[Total 5 marks]

Bishop Thomas Grant School 2


4. A rocket is powered by the reaction between methylhydrazine and dinitrogen tetroxide.

4CH3NHNH2(l) + 5N2O4(l) → 4CO2(g) + 12H2O(l) + 9N2(g)

A partially completed dot-cross diagram and a full structural formula for


methylhydrazine are shown below.

(i) Complete the dot-cross diagram for methylhydrazine, showing all the outer shell
electrons.

H H
A
H C H N C NN HN H
B
H H H H H H
[2]

(ii) Give approximate values for the bond angles A and B in the methylhydrazine
molecule.

A ............................................................ B ............................................................
[2]
[Total 4 marks]

Bishop Thomas Grant School 3


5. Titanium alloys are often used for reaction vessels in the chemical industry because of
their high chemical resistance. However, they cannot be used with concentrated
hydrochloric acid. This reacts with titanium to form a mixture of coloured ions.

(i) One of the coloured ions formed when titanium reacts with hydrochloric acid is
3+
the hexaaquatitanium(III) ion, [Ti(H2O)6] (aq).

In the box below, draw the shape of this complex ion indicating the charge on the
ion.

Give the name for the shape of this complex ion.

shape of complex ion ......................................................


[3]

+
(ii) The [Ti(H2O)4Cl2] ion is also formed in concentrated hydrochloric acid. Suggest
why there are two possible structures for this ion.

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[2]
[Total 5 marks]

Bishop Thomas Grant School 4


6. Nitrous oxide, N2O, can be injected into an internal combustion engine in order to
significantly increase power output.

Nitrous injection has been used in high performance cars such as dragsters and even
in aircraft engines.

(a) The bonding in nitrous oxide can be represented as follows.

N≡N → O
Draw an electron ‘dot-cross’ diagram for this molecule. Use the outline below.

N N O
[4]

(b) At the high temperature of the engine’s combustion chamber, nitrous oxide
decomposes into nitrogen gas and oxygen gas. This means more oxygen is
available during combustion and therefore more fuel can be burnt.

(i) The equation for the decomposition is given below.

2N2O(g) → 2N2(g) + O2(g)

Use the following bond enthalpy data to calculate the enthalpy change for
this reaction.

–1
bond bond enthalpy / kJ mol
N≡N (in N2O) +481
N≡N (in N2 gas) +945
O=O (O2) +498
N→O (in N2O) +167

–1
enthalpy change = ................................... kJ mol
[4]

Bishop Thomas Grant School 5


(ii) Another oxide of nitrogen, nitrogen monoxide, NO, does not decompose
completely under the conditions present in the combustion chamber. This is
because the bond enthalpy of the nitrogen–oxygen bond in this molecule is
much greater than that in nitrous oxide.

What can you conclude from the above information about the N–O bond length in
nitrogen monoxide compared to that in nitrous oxide?

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[1]

(c) The decomposition of nitrous oxide, as shown in the equation below, is


accompanied by an increase in entropy.

2N2O(g) → 2N2(g) + O2(g)

Explain why there is an increase in entropy for this decomposition.

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[1]
[Total 10 marks]

7. One example of an HFC is CH2F2. The C – F bond is polar.

(i) Mark partial charges (δ – and δ + ) on the C and F atoms in the structure below.

H

FCF

H
[1]

(ii) Explain what determines where the partial charges are placed on this molecule.

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[2]

Bishop Thomas Grant School 6


(iii) Does the whole molecule have a dipole? Explain your answer.

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[2]
[Total 5 marks]

8. ‘Low sulphur fuel’ is now a familiar label on the pumps at petrol stations. The removal
of sulphur from diesel and petrol significantly reduces the emission of toxic oxides of
sulphur from vehicle exhausts.

(i) One oxide of sulphur is the gas sulphur dioxide, SO2.

One way to represent the bonding in sulphur dioxide is given below.

O = S →O
Use the structure above to draw a dot-cross diagram in the box below.
Show all outer electrons.

O S O
[3]

(ii) The actual shape of the sulphur dioxide molecule is ‘V’-shaped.

Explain why you would predict this shape for the SO2 molecule.

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[3]
[Total 6 marks]

Bishop Thomas Grant School 7


9. The polymer commonly known as PVC exists in two forms. Plasticised PVC is used
where flexibility is required. Unplasticised PVC, uPVC, is rigid at room temperature and
is used to make things such as guttering for houses.

PVC owes many of its properties to the intermolecular forces between the polymer
chains.

(i) Name the strongest type of intermolecular force that is present in PVC.

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[1]

Bishop Thomas Grant School 8


(ii) Use the diagram below to show how these intermolecular forces hold the PVC
chains together.

C 2
H C H 2
C H C H 2
C H

C l C l

C 2H C H C 2H C H C 2H

C l C l
[2]
[Total 3 marks]

Bishop Thomas Grant School 9


–3 –3
10. (a) Phenobarbitol has a low solubility of 4.3 × 10 mol dm in water.

(i) The C O and N–H groups encourage solubility in water by hydrogen


bonding.

On the diagram below, show how water molecules form hydrogen bonds
with each of C O and N–H. Show lone pairs and partial charges.

O O
N

C 2 H 5
N
H

O
[4]

Bishop Thomas Grant School 10


(ii) Name the part of the molecule that inhibits the solubility of phenobarbitol in
water.

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[1]

Bishop Thomas Grant School 11


H

O O
N

C 2 H 5
N
H

(b) Phenobarbitol is acidic. The acidic proton is shown by the arrow in the structure
above.

Complete the structure below to show both the ions present in the salt that
phenobarbitol forms with sodium hydroxide.

O O
N

C 2 H 5
N

O
[2]
[Total 7 marks]

Bishop Thomas Grant School 12


11. Large quantities of chloromethane, CH3Cl, and bromomethane, CH3Br, are released
into the Earth’s troposphere (lower atmosphere) each year from marine life in the
oceans.

(a) Name the homologous series of compounds to which both chloromethane and
bromomethane belong.

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[1]

Bishop Thomas Grant School 13


(b) Chloromethane and bromomethane are both gases at room temperature whilst
water is a liquid.

(i) Water molecules are held together by hydrogen bonds. Draw a diagram to
show how two water molecules can be linked by a hydrogen bond. Include
relevant lone pairs and partial charges in your diagram.

[4]

Bishop Thomas Grant School 14


(ii) Describe two features of a water molecule that enable it to form hydrogen
bonds.

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[2]

Bishop Thomas Grant School 15


(iii) Name the strongest type of intermolecular force that can form between
molecules of chloromethane.

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[1]

Bishop Thomas Grant School 16


(iv)

boiling point / K
bromomethane 277
chloromethane 249
water 373

Use ideas about intermolecular forces to explain:

• why chloromethane has a lower boiling point than water;

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• why bromomethane has a higher boiling point than chloromethane.

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[3]
[Total 11 marks]

Bishop Thomas Grant School 17


12. In this question, one mark is available for the quality of the use and organisation of
scientific terms.

Compound C is an isomer of myrcene. It has the structure shown below.

C H 2 C HC H C 3H C H

H 3 C C H C 2H C H
c o m p o u n d C

H 3 C C H C 2H C H

C C 2H C C 2H
m y r c e n e
C 3H C 2H

Bishop Thomas Grant School 18


Both compound C and myrcene have instantaneous dipole-induced dipole forces of
attraction between their molecules. Compound C has a higher boiling point than
myrcene. Explain this in terms of intermolecular forces.

Bishop Thomas Grant School 19


In your answer you should refer to:

• how instantaneous dipole–induced dipole forces arise;

• how these forces can be used to account for the higher boiling point of
compound C compared to that of myrcene.

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[5]
Quality of Written Communication [1]
[Total 6 marks]

Bishop Thomas Grant School 20


13. Seaweed and marine algae produce the gas dimethylsulphide, DMS. In the
atmosphere this is oxidised to two other compounds whose structures are shown
below.

H 3 C H 3 C H 3 C O

S S O S

H C H C H C O
3 3 3

DMS DMSO MSM


dimethyl sulphide dimethylsulphoxide methylsulphonylmethane

DMSO is used as an industrial solvent and occasionally as a medicine. MSM is


marketed as a medicine to provide sulphur to build body protein.

DMSO is liquid at room temperature. It is used as a solvent because it can dissolve


non-polar solutes but it is also very soluble in water.

Bishop Thomas Grant School 21


(i) DMSO has a relatively small dipole. One reason is that the S O bond is not
very polar.
Explain why this is so.

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[1]

Bishop Thomas Grant School 22


(ii) Some molecules have strongly polar bonds but still have little or no overall dipole.
Suggest why.

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[2]

Bishop Thomas Grant School 23


(iii) One molecule of DMSO forms hydrogen bonds with two molecules of water.
Complete the diagram below to illustrate this, showing lone pairs and partial
charges.

H 3 C

S O

H 3 C
[4]
[Total 7 marks]

Bishop Thomas Grant School 24


14. Seaweed and marine algae produce the gas dimethylsulphide, DMS. In the
atmosphere this is oxidised to two other compounds whose structures are shown
below.

H 3 C H 3 C H 3 C O

S S O S

H C H C H C O
3 3 3

DMS DMSO MSM


dimethyl sulphide dimethylsulphoxide methylsulphonylmethane

DMSO is used as an industrial solvent and occasionally as a medicine. MSM is


marketed as a medicine to provide sulphur to build body protein.

Bishop Thomas Grant School 25


(i) Complete the dot-cross diagram for DMS to show the outer shell electrons
around the sulphur atom.

H S H
+ +
+ C C
+ H
H + +
H H
[2]

Bishop Thomas Grant School 26


S
(ii) Suggest a value for the C C in DMS. Explain how you arrived
bond angle
at your answer.

angle ......................................................... º

explanation ....................................................................................................

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[3]
[Total 5 marks]

Bishop Thomas Grant School 27


15. One reason for the new treatment of water with ozone was the concern that domestic
water supplies were being contaminated with halogenoalkanes, such as CHCl3. These
form when plant matter decays. The organic compounds then enter the river water.
Ozone breaks down these organic contaminants.

(i) Give the systematic name for CHCl3.

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[1]

Bishop Thomas Grant School 28


(ii) The C–Cl bond is polar. On the diagram of the CHCl3 molecule shown below,
mark the partial charges on the C and Cl atoms.

C l

H C C l

C l
[1]

Bishop Thomas Grant School 29


(iii) Draw a diagram to represent the shape of a molecule of CHCl3.
[1]

Bishop Thomas Grant School 30


(iv) In this question, one mark is available for the quality of spelling, punctuation and
grammar.

• Explain why the molecule CHCl3 has the partial charges you have shown in
(ii).

• Describe the shape you drew in (iii) and explain whether or not this leads to
an overall permanent dipole for the molecule.

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[4]
Quality of Written Communication [1]
[Total 8 marks]

Bishop Thomas Grant School 31


16. (a) A molecule that has the same effect on the body as GHB is called ‘GHB
alcohol’. Its structure is shown below, together with the structure of GHB.

H H H H H H H
O
H O C C H C O C C C C C
H H O HH H H H H
G H B G H B a l c o h o l

(i) On the molecule of GHB above, draw a ring round the largest part of the
molecule that could be the pharmacophore.
[1]

Bishop Thomas Grant School 32


(ii) Suggest why both of these molecules are able to bind to the same receptor
site in the body. Name the intermolecular bonds involved.

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[3]

Bishop Thomas Grant School 33


(b) Chemists are constantly seeking new medicines, starting from known
pharmacophores.

(i) Name a modern technique that allows chemists to view the possible ways
in which a molecule can bind on to a receptor site.

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[1]

Bishop Thomas Grant School 34


(ii) Suggest how chemists might justify continuing to manufacture GHB when it
has been implicated as a ‘date-rape’ drug.

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[2]
[Total 7 marks]

Bishop Thomas Grant School 35


17. (a) The C–Cl bond in chloromethane is slightly polar. On the diagram of the
CH3Cl molecule shown below, mark the partial charges on the atoms.

H C C l

H
[1]

Bishop Thomas Grant School 36


(b) Draw a diagram to represent the three-dimensional shape of a molecule of
CH3Cl and give the bond angle.

Bond angle: ...................................................................... °


[2]
[Total 3 marks]

Bishop Thomas Grant School 37


18. One example of an HFC is CH2F2. The C–F bond is polar.

(i) Mark partial charges on the C and F atoms in the structure below.

F F C

H
[1]

Bishop Thomas Grant School 38


(ii) Explain what determines where the partial charges are placed on this molecule.

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[2]

Bishop Thomas Grant School 39


(iii) Does the whole molecule have a dipole? Explain your answer.

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[2]
[Total 5 marks]

Bishop Thomas Grant School 40


19. Some microorganisms in seawater can convert chloride ions into chlorine-containing
molecules, such as chloromethane, CH3Cl. Chloromethane is then released into the
atmosphere.

(i) Explain, in terms of intermolecular bonds, why chloromethane has a lower boiling
point than water.

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[1]

(ii) Draw a diagram showing how two molecules of chloromethane, CH3Cl, would
form one intermolecular bond. Include relevant partial charges.

[2]

Bishop Thomas Grant School 41


(iii) Chloromethane is slightly soluble in water. Give the strongest type of
intermolecular bond that could form between molecules of chloromethane and
water.

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[1]

(iv) In the atmosphere, C–Cl bonds in chloromethane molecules can be broken when
the molecules absorb energy.
–1
The bond enthalpy of the C–Cl bond is +346 kJ mol .

Calculate the minimum energy (in Joules) needed to break a single C–Cl bond.
23 –1
Avogadro constant, NA = 6.02 × 10 mol

minimum energy = ...................................................... J


[2]

Bishop Thomas Grant School 42


(v) Calculate the frequency of radiation that is needed to break one C–Cl bond.

Give your answer to three significant figures.


–34 –1
Planck constant, h = 6.63 × 10 J Hz

frequency = ................................................... Hz
[3]
[Total 9 marks]

Bishop Thomas Grant School 43


20. A student decided to make some propene from propan-1-ol.

Propan-1-ol is a liquid at room temperature, whilst propene is a gas. The strongest type
of intermolecular bond between propan-1-ol molecules is hydrogen bonding.

(i) Draw a diagram to show the hydrogen bonding between two propan-1-ol
molecules.
Include relevant lone pairs and partial charges in your diagram.

[4]

Bishop Thomas Grant School 44


(ii) Propan-1-ol has a higher boiling point than propene. Explain this in terms of
intermolecular bonding.

In your answer, you should make it clear how the steps you describe are linked
to one another.

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[4]
[Total 8 marks]

Bishop Thomas Grant School 45


21. Radiowaves can provide information about the molecules found in some regions of
space.

(i) One molecule found in the coldest regions of outer space has the formula H2CO.
This molecule can be represented as:

C O

Bishop Thomas Grant School 46


Draw the ‘dot-and-cross’ diagram for this molecule.
[3]

Bishop Thomas Grant School 47


(ii) Use your diagram from (i) to help you describe and explain the shape of H2CO,
giving the bond angle.

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[5]
[Total 8 marks]

Bishop Thomas Grant School 48


22. (a) One physical property chemists examined was the melting point of the
elements. This is tabulated below for the Period 2 elements.

element Li Be B C N O F Ne
(diamond)

atomic number 3 4 5 6 7 8 9 10

melting point / K 453 1560 2349 3800 63 55 53 25

(i) Describe the pattern in melting point as you go across the period.

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[1]

Bishop Thomas Grant School 49


(ii) The change in melting point across the period can be explained in terms of
the structure and bonding of the elements.

Describe the changes, both in type of bonding and in structure, as the


period is crossed from left to right.

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[4]

Bishop Thomas Grant School 50


(b) The electron structure of an element is 2.8.8.2.

In which group and period of the modern Periodic Table is this element found?

Group .................................................. Period ..................................................


[1]
[Total 6 marks]

Bishop Thomas Grant School 51


23. (i) Predict the shape and bond angle around the lead atom in lead tetraethyl.

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[2]

Bishop Thomas Grant School 52


(ii) Explain your answer to (i).

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[3]
[Total 5 marks]

Bishop Thomas Grant School 53


24. Explain, in terms of intermolecular bonds, why chlorine is a gas at room temperature
and pressure but bromine is a liquid under the same conditions. As part of your
answer, you should explain how the intermolecular bonds arise.

In your answer, you should use appropriate technical terms, spelt correctly.

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[Total 5 marks]

Bishop Thomas Grant School 54

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