Revision Sheet Term 2 Final Level –O-12IP

True
The International School
Of Choueifat
Level 12IP –OIP Chemistry March,2014
Revision Sheet
A2 chs 3-12
Term II Final
All the number of problems are related to following revision sheet

SABIS Proprietary Page 1 of 54

 Level O Class Work Home work

Chs 3-5 Questions 1,4 and 5

Discuss HW
Period 1 Chs 6-9 Questions 7,8 and9
Chs 3-5 Questions2,3&6
Discuss HW
Period 2 Chs 6-9 Questions 13&14 and 17
Chs 6-9 Questions 10,11and12,
Discuss HW
Period 3 Chs 6-9 Question 15,16 &19 Chs 10-11 Questions 23,24 and 29

Discuss HW Ch 12 Questions 27&28

Period 4
Chs 10-11 Questions 18,20,21&22 Ch 9 Question 30
Discuss HW
Period 5 Review term 2 periodics
Ch 12 Questions 25&26

Period 6 Review term 2 periodics

Reference: A2

Revision Sheet Level O

1- This question concerns the efficiency and economics of the Haber Synthesis of
ammonia:

N2(g) + 3H2(g) 2NH3(g) ∆H = -92 kJ / mol

Equilibrium concentrations of ammonia will be greater at high pressures and low

temperatures. Typical values used industrially are 500C and 200 atm which gives
about 15% conversion to ammonia at equilibrium.

a) Explain in molecular terms, why a temperature lower than the one quoted is
not used.
___________________________________________________
 ___________________________________________________

___________________________________________________

___________________________________________________
(3m)
a) Explain why a pressure higher than the one quoted is not
often used.

___________________________________________________

_______________________________________________

___________________________________________________

___________________________________________________
(2m)

c) The gases are passed through a conversion chamber containing beds of

granulated iron which acts as a catalyst

Describe and explain the effects of iron on:

i) the rate of the production of ammonia

___________________________________________________

___________________________________________________

___________________________________________________

___________________________________________________
(2m)

ii) the amount of ammonia in the equilibrium

mixture

___________________________________________________

___________________________________________________

___________________________________________________

___________________________________________________
(2m)
Total Q1= 9 marks
2-. Many industrial processes form HCl as a product. HCl can be oxidised to chlorine:

4HCl(g) + O2(g) 2Cl2(g) + 2H2O(g)

0.800 mol of HCl was mixed with 0.200 mol of O2 in a vessel of volume 10.0 dm3
in the presence of a catalyst at 400C. At equilibrium it was found that the mixture
contained 0.200 mol of HCl.

i) Write the expression for Kc

(1m)

ii) Calculate the value of Kc at 400C

(4m)
TotalQ2 = 5 marks
3- The colourless gas N2O4 dissociates into brown NO2 gas.

N2O4(g) 2NO2(g) ∆H = + 58.1 kJ / mol

a) Write an expression for Kp for this reaction.

(1 m)

b) At 400K N2O4 is 80% dissociated. Calculate the value of Kp at this

temperature knowing that the total pressure at equilibrium was found to be
6.75 atm.

(5m)

c) A sealed vessel containing an equilibrium mixture of the gases is warmed

gently.

i) What happens to the value of Kp? Explain.

___________________________________________________

___________________________________________________

___________________________________________________

___________________________________________________
(3m)
 ii) What would you observe as the mixture is heated?

___________________________________________________

__________________________________________________

___________________________________________________
(1m)
TotalQ3= 10 marks

4- a) Calculate the concentration of a solution of hydrochloric acid, HCl

which has a pH of 1.13

(1m)

b) Calculate the concentration of a solution of chloric (I) acid HOCl

which has a pH of 4.23. (Ka HOCl = 3.72 x 10-8 mol dm-3)

(4m)
Total Q4= 5 marks

5- a) What is meant by the term weak acid?

__________________________________________________________________

__________________________________________________________________

__________________________________________________________________

__________________________________________________________________
(2m)
b) A weak acid HA dissociates in water:

HA(aq) + H2O(l) H3O+(aq) + A-(aq)

Write an expression for Ka of HA.

(1m)
c) 25cm3 of 1.00 mol dm-3 aqueous HA was titrated against 1.00 mol dm-3
aqueous NaOH and the pH measured. The titration curve is shown below:

Use the curve to find:

i) the value of the pH at the end point of the titration.

__________________________________________________________________
(1m)
ii) the pH of an aqueous solution of the salt NaA.

__________________________________________________________________
(1m)

iii) the value of pKa for the acid HA and hence the value of Ka.

pKa:

Ka:
(2m)
d) Some of the solutions made during this titration would act as buffer
solutions.

i) What is meant by the term buffer solution?

__________________________________________________________________

__________________________________________________________________

__________________________________________________________________

__________________________________________________________________
(2m)

ii) Use the titration curve to find:

the range of pH values over which this mixture acts as a buffer.

(1m)
the pH of the most efficient buffer.

(1m)
TotalQ5 = 11 marks
6- The weak acud HCOOH dissociates in water:

HCOOH(aq) + H2O(l) H3O+(aq) + HCOO-(aq)

The acid dissociation constant Ka for HCOOH at 298K is 1.78 x 10-4 mol dm-3.

a) A 0.200 mol dm-3 solution of HCOOH has a pH of 2.20 at 298 K.

20.0cm3 of this solution is titrated with 0.100 mol dm-3 NaOH solution until
excess alkali has been added. Sketch a titration curve of pH versus volume
of NaOH added.

(4m)

b) Equal volumes of 0.500 mol dm-3 methanoic acid (HCOOH) and 0.250 mol
dm-3 sodium methanoate (HCOONa) are mixed to make a buffer solution.

i) Show, using equations, how this buffer works.

__________________________________________________________________

__________________________________________________________________

__________________________________________________________________

(2m)

ii) Calculate the pH of this buffer solution.

(3m)
TotalQ6 = 11 marks
7- a) What is meant by a Brønsted-Lowry acid?

__________________________________________________________________
(1m)

(b) Propanoic acid, CH3CH2COOH, dissociates in water and has

a Ka value of 1.30 × 10-5 mol dm-3 at 25°C.
CH3CH2COOH + H2O  CH3CH2COO- + H3O+

What assumptions have to be made when calculating the

H3O+ ion concentration? Explain whether it is justified.

__________________________________________________________________

__________________________________________________________________

__________________________________________________________________

__________________________________________________________________

__________________________________________________________________

__________________________________________________________________
(2)

c) A solution of sodium propanoate in water is alkaline.

i) Write an ionic equation to show why a solution of

sodium
propanoate is alkaline.

__________________________________________________________________
(1)
 ii) The pH of a solution of sodium propanoate of
concentration 0.100 mol dm-3 is 8.94 at 25°C.
Calculate the concentration of the hydroxide ions in
this solution.
[Kw = 1.00 × 10-14 mol2 dm-6 at 25°C]

(2)

d) An aqueous mixture of propanoic acid and sodium

propanoate is a buffer.

Explain why the pH of a buffer does not change when it is

diluted with water.

__________________________________________________________________

__________________________________________________________________

__________________________________________________________________

__________________________________________________________________

__________________________________________________________________

__________________________________________________________________

__________________________________________________________________

__________________________________________________________________
(1)
TotalQ7 = 7 marks
 8- Two compounds, A and B, are isomers with molecular formula C4H8O.

• Both compounds produce an orange-yellow precipitate with 2,4-

dinitrophenylhydrazine.

• Both compounds react with sodium borohydride (sodium

tetrahydridoborate(III)) or
Lithium aluminium hydride (tetrahydridoaluminate(III).

• When the compounds are warmed separately with Fehling’s solution, A forms
a red-brown
precipitate but B does not.

• Compound B forms yellow crystals when warmed with aqueous iodine and
sodium
hydroxide, whereas A does not.

(a) Draw full structural formulae for A and B, showing all bonds.

(2m)

(b) Draw the structural formula of the product from the reaction of compound A
with
2,4-dinitrophenylhydrazine.

(2m)

(c) Give the name and formula of:

 (i) The yellow solid formed when compound B reacts with aqueous iodine and
sodium hydroxide:

(2m)

(ii) The organic product of the reaction between compound B and sodium
borohydride
(sodium tetrahydridoborate(III)) or Lithium aluminium hydride
( tetrahydridoaluminate(III)) in water:

(2m)

(d) Molecules of the organic product formed in (c)(ii) are chiral and exist as
optical isomers.

(i) What is meant by the term chiral molecule?

_____________________________________________________________________________

_____________________________________________________________________________
(1m)

(ii) How could the optical isomers of the compound formed in (c)(ii) be
distinguished from each other?

_____________________________________________________________________________

_____________________________________________________________________________
(1m)
Total Q8 = 10 m

9- a)Describe what you would see and write the equations for the reactions of propanoic acid
with:

(i) A solution of sodium carbonate

Observation ............................................................................................................

Equation .................................................................................................................
 (2m)
(ii) Solid phosphorus pentachloride.

Observation ............................................................................................................

Equation .................................................................................................................

(2m)

b) Propanoic acid can also be prepared from propanal, CH3CH2CHO. State the reagents for this
conversion.

Reagents ........................................................................................................................

(2m)

c) 1-aminobutan-2-ol, CH3CH2CH(OH)CH2NH2, is an active ingredient in some deodorant sprays.

It can be prepared from propanal by the following two-step process.

(i) For Step 1

State the reagents and conditions.

_____________________________________________________________________________

_____________________________________________________________________________

Name the type of reaction.

_____________________________________________________________________________
(3m)
Total Q9 = 9 m

10-a In moths a pheromone, P, acts as an attractant for the opposite sex. P has the molecular
formulaC7H12O.

What can be deduced about the structure of P from the following information?

(a) (i) 1 mole of P reacts with 1 mole of Br2 molecules to form a compound with the formula
C7H12OBr2.
_____________________________________________________________________________

_____________________________________________________________________________
(1m)

(ii) When lithium tetrahydridoaluminate is reacted with P a compound with the formula C7H14O
is formed.

_____________________________________________________________________________

_____________________________________________________________________________
(1m)

(iii) P forms an orange precipitate with 2,4-dinitrophenylhydrazine.

_____________________________________________________________________________
(1m)

(iv) When P is heated with Fehling’s or Benedict’s solution, the solution remains blue.

_____________________________________________________________________________

_____________________________________________________________________________

(1m)

(v) P is a Z-isomer.

_____________________________________________________________________________

_____________________________________________________________________________
(1m)

(b) What does the following physical data tell you about the structure of P? Use the Data booklet
attached where necessary.

(i) The infrared spectrum of P has the following absorptions at wave numbers above
1600 cm–1.
3060 cm–1
2920 cm–1
 1690 cm–1
1660 cm–1

_____________________________________________________________________________

_____________________________________________________________________________

_____________________________________________________________________________
(3m)

(ii) The nmr spectrum does not have a peak corresponding to a chemical shift, δ, of
between 9 and 10.

_____________________________________________________________________________

_____________________________________________________________________________
(1m)

(iii) The mass spectrum showed the presence of peaks at mass/charge ratios of 15 and 29, but no
peak at 43.

_____________________________________________________________________________

_____________________________________________________________________________

_____________________________________________________________________________
(3m)

(c) Given that P has a straight chain of carbon atoms in its formula, use the information you have
deduced above to suggest a displayed formula for the pheromone P.

(2m)

(d) How could you use a purified sample of the orange precipitate in (a)(iii) to confirm the formula
of P?

__________________________________________________________________________

__________________________________________________________________________
(2m)
Total Q10 = 16 m

11- Terylene is a polymer made from ethane 1,2-diol and benzene- 1,4-dicarboxylic acid. It is a
condensation polymer.
 (a) Draw the structural formulae of the two compounds which are used to make Terylene.

(2m)

(b) Give a structural formula for the polymer.

(2m)

(c) Explain the meaning of the term condensation in this context.

_____________________________________________________________________________
(1m)

(d) Suggest why polyesters are not suitable for use under strongly alkaline conditions.

_____________________________________________________________________________

_____________________________________________________________________________
(1m)
Total Q11 = 6 m

12- The following procedure can be used to prepare ethyl ethanoate (boiling
temperature 77°C).

• Mix 20 cm3 of ethanol (an excess) and 12.6 g of ethanoic acid in a pear-shaped
flask.
• Slowly add 8 cm3 of concentrated sulphuric acid, with cooling and mixing.
• Heat the mixture under reflux for 15 minutes.
• Allow the apparatus to cool and then re-arrange it for distillation.
• Collect everything that distils up to 80°C.
• Purify the distillate.

(a) Write the equation for the reaction between ethanol and ethanoic acid.

________________________________________________________________________________
 ________________________________________________________________________________
(1m)

(b) What is the purpose of the concentrated sulphuric acid in this reaction?

________________________________________________________________________________
(1m)

(c) Draw a diagram to show how you should set up the apparatus to distil the
mixture.

(4m)

(d) 10.6 g of pure ethyl ethanoate was collected.

Calculate the percentage yield of ethyl ethanoate obtained in this experiment.

(3m)
(e) Ethyl ethanoate can also be prepared from ethanol and ethanoyl chloride.

(i) Write the equation for this reaction.

_____________________________________________________________________________
 (1m)
(ii) Explain why the yield obtained by this method is significantly higher than
that from ethanoic acid.

_____________________________________________________________________________

_____________________________________________________________________________
(1m)
Total Q12 = 11 m

13-(a) Primary alcohols can be oxidised to aldehydes. The following are the instructions for the
oxidation of ethanol (boiling temperature 78 ºC) to ethanal (boiling temperature 21 ºC).

· Place 50 cm3 of water in a round bottom flask and add, carefully with stirring, 17 cm3 of
concentrated sulphuric acid. Arrange the flask, with a tap funnel attached, in a distillation apparatus.

· Dissolve 50 g of sodium dichromate(VI) in 50 cm3 of water and add 40 cm3 of ethanol, mix and
place in the tap funnel.

· Heat the dilute acid in the flask until it is boiling and then remove the flame.

· Slowly run the solution of sodium dichromate(VI) into the flask. A vigorous reaction takes place.

· Collect the mixture of ethanal and water, which distils off, in a conical flask, which is
surrounded by iced water.

(i) Draw a diagram of the apparatus which could be used for this reaction.

(3m)
 (ii) Explain why the ethanol and the oxidising agent are not initially placed in the round-
bottomed flask with the sulphuric acid.

_____________________________________________________________________________
(1m)

(iii) Explain why the heat is removed before the solution of ethanol and sodium
dichromate(VI) is added.

_____________________________________________________________________________

_____________________________________________________________________________
(1m)

(iv) Suggest why the flask in which the product is collected is surrounded by iced water.

_____________________________________________________________________________

_____________________________________________________________________________
(1m)

b) Butanone can be made from 2-bromobutane by a synthetic route involving two steps, the first using
aqueous sodium hydroxide and the second potassium dichromate(VI) solution acidified with dilute
sulphuric acid.

Give the structural formula of the intermediate compound in this synthetic route.

(1m)
Total Q13 = 7 m

14- Compound V, the structure of which is shown below, is found in human sweat.
a) Compound V has two functional groups. Identify both functional groups and state a chemical test for
each. The result of each chemical test should be included in your answer.

(4m)

b) Compound V can be converted into two carbonyl compounds, W and X shown below:

i) Which of the compounds, W or X would react when warmed with Fehling’s solution? Justify
your answer.

_____________________________________________________________________________

_____________________________________________________________________________
(1m)

ii) Compound W can be reduced in two steps to compound Y of molecular formula C2H6O2.

Identify Y:

(1m)

iii) Compound W can be oxidized to compound Z of molecular formula C2H2O4.

Identify Z:
 (1m)

c) The compound Y and Z react together under certain conditions to form a polymer.

i) Draw the structural formula of the repeating unit for the polymer formed

(2m)

ii) What type of polymerization reaction occurs between compounds Y and Z?

________________________________________________________________________________
(1m)
Total Q14 = 10 m

15- This question concerns the compounds in the following reaction scheme:

(a) F and G are compounds which both decolorise bromine water. F has two stereoisomers.

(i) What functional group is present in both F and G?

_____________________________________________________________________________
(1m)

(ii) Give the structural formulae of both stereoisomers of F.

 (2m)

(iii) Explain how these two isomers arise.

_____________________________________________________________________________

_____________________________________________________________________________
(2m)

(iv) Write the structural formula of G.

(1m)

(b) B cannot be oxidised by acidified potassium dichromate(VI) solution.

(i) Write the structural formula of B.

(1m)

(ii) Draw the general structural features of molecules which can be detected by the reaction with
iodine and alkali.

(2m)

(iii) Give the structure of the substance in solution D, and of the product E.
 (2m)

(c) The mass spectrum of A gives peaks at m/e 29 and 45, amongst others. That at 45 is the
largest. This spectrum shows no molecular ion peak, which would be expected at m/e 74. A is
chiral.

(i) Give the structural formula for A.

(1m)

(ii) Identify the ions responsible for the peaks at m/e 45 and 29, and hence suggest why the
molecule shows no molecular ion peak.

_____________________________________________________________________________

_____________________________________________________________________________

_____________________________________________________________________________
(3m)
(Total Q 15= 15 marks)

16- Compounds A and B are structural isomers.

a. (i) The mass spectrum of one of the compounds is shown below. Explain how the fragmentation
pattern allows you to deduce that it is not compound B.
 [2]

(ii) Write an equation to show the formation of the molecular ion for compound A.

[1]
b. One of the compounds A or B gives the infrared spectrum below.
 Using the Data Sheet at the end of the exam, identify which of the two compounds A or B has this
spectrum. Explain your reasoning carefully.

[2]

(Total Q 16= 5 marks)

17- Two compounds, A and B, are isomers with molecular formula C4H8O.
• Both compounds produce an orange-yellow precipitate with
2,4-dinitrophenylhydrazine.
• Both compounds react with sodium borohydride (sodium tetrahydridoborate(III)).
• When the compounds are warmed separately with Fehling’s solution, A forms a
red-brown precipitate but B does not.
• Compound B forms yellow crystals when warmed with aqueous iodine and
sodium hydroxide, whereas A does not.

(a) Draw full structural formulae for A and B, showing all bonds.

Full Structural formula

Compound A

Compound B

(2)

b) Give the name and formula of:

(i) the yellow solid formed when compound B reacts with aqueous iodine and
sodium hydroxide:
name .......................................................................................................................
formula
(2)
(ii) the organic product of the reaction between compound B and sodium borohydride
(sodium tetrahydridoborate(III)) in water:
name .......................................................................................................................
formula
(2)
(c) Molecules of the organic product formed in (c)(ii) are chiral and exist as optical
isomers.
(i) What is meant by the term chiral molecule?
...............................................................................................................................
...............................................................................................................................
...............................................................................................................................
(1)
(ii) How could the optical isomers of the compound formed in (c)(ii) be distinguished
from each other?
...............................................................................................................................
...............................................................................................................................
(1)

(d) Draw the structural formula of the product from the reaction of compound A with
2,4-dinitrophenylhydrazine.
(2)

(e) Compound C has the molecular formula C4H8O.

• When phosphorus pentachloride, PCl5, was added to a dry sample of C, steamy
 fumes were observed.
• When bromine water was shaken with a sample of C, the bromine water turned
colourless.
• Compound C can be oxidised to a carboxylic acid which has a geometric
isomer.
Use the information above to draw the formulae of the two isomers which could be
compound C.

(2)
(TotalQ17= 12 marks)

18-
 (2 marks)

Total Q 18= 11 marks

19-
 Total Q 19= 8 marks

20-

Total Q20 = 9 m
21- a- Cr3+(aq) + e- Cr2+(aq) E=-0.41V
Cr2O72-(aq) + 14H+(aq) + 6e- 2Cr3+(aq) + 7H2O(l) E=+1.33V
S(S) + 2H+(aq) + 2e- H2S(aq) E=+0.14V

(i) Hydrogen sulfide , H2S, reduces dichromate(VI) ions in acid solution. Is the product
Cr3+ ions or Cr2+ ions? Justify your answer by calculating the Ecell values for the
possible reductions.

(4m)

(ii) Write the ionic equation for the reaction that takes place between
hydrogen sulfide and dichromate(VI) ions in acid solution.
 (2m)

(iii) Define disproportionation.

(1m)
(iv) Explain in terms of E values , wether Cr3+(aq) ions will disproportionate.

(2m)
b- The water from volcanic hot springs often contains significant amount of the poisonous gas
hydrogen sulfide. The amount present can be measured by titration against a standard
solution of acidified potassium manganate (VII).
5H2S(g) + 2 MnO4- + 6H+ 2Mn2+ + 5S +8H2O
A portion of hot spring water of volume 250 cm3 was taken and 50.0 cm3 portions were
titrated against acidified 0.0100 mol dm-3 potassium manganate (VII). The mean titre of
was 7.55 cm3. Calculate the volume of hydrogen sulfide dissolved in the 250 cm3 sample of
hot spring water.( 1 mole of gas under the conditions of the experiment ,has a volume of
24000 cm3)

(4m)
Total Q21 = 13 m
22- (a) Cobalt has only one naturally occurring type of atom, Co, but the isotope Co can be made
artificially.

(i) Define the term atomic number

(1 mark)

(ii) What is the difference between the atomic structures of Co and Co?

(1 mark)

(iii) Why do both isotopes have the same chemical reactions?

(1 mark)

(b) Give the electronic configuration of a cobalt atom and a Co2+ ion.

(2 marks)

(c) Cobalt can be described both as a d-block element and as a transition element.

State what is meant by each of the terms.

(i) d-block element ____________________________________________

__________________________________________________________

__________________________________________________________
 (1 mark)

(ii) Transition element___________________________________________

__________________________________________________________

__________________________________________________________
(1 mark)

(d) In aqueous solution water combines with the Co2+ ion to form the complex ion [Co(H2O)6]2+
which gives a pink colour to the solution.

(i) What feature of the water molecule allows it to form a complex ion with Co2+?

(1 mark)

(ii) What types of bond are present in the complex ion [Co(H2O)6]2+?

(2 marks)

(iii) Suggest the shape of the ion [Co(H2O)6]2+.

__________________________________________________________
(1 mark)

(e) Consider the following reactions

(i) Give the name of the blue precipitate, A, and write an ionic equation for its formation from
[Co(H2O)6]2+.
 (2 marks)

(ii) What name is given to the type of reaction occurring in (i)?

(1 mark)

(iii) Suggest a formula for the cobalt complex ion B present in the solution.

(1 mark)

(i) Write an equation for the formation of ion D from [Co(H2O)6]2+ and suggest the type of
reaction taking place.

(2 marks)
(Total Q22=17 marks)

23- (a) (i) Enter the electron structures required in the boxes below.

(2 marks)
(ii) How is the electron structure of Cr unusual, and why?

(2 marks)

(b) (i) Calculate the oxidation number of Mn in MnO42-.

(2 marks)
 (ii) Why does Sc form only Sc3+ ions?

(2 marks)

(iii) Why are transition metals able to show a variety of oxidation states?

(2 marks)

(c) Fe2+ ions will catalyse the reaction between peroxodisulphate ions and iodide ions, which
otherwise is slow: the uncatalysed exothermic reaction is

S2O8 +2I- 2SO4 +I2

and the catalysed steps are:

2Fe2+ + S2O8 2SO4 + 2Fe3+

2Fe3+ + 2I- 2Fe2+ + I2

(i) Sketch reaction profiles (enthalpy level diagrams) for both the uncatalysed and the
catalysed reactions. Label each profile.

(4 marks)

(ii) Examine the equations for the catalysed steps of the reaction. Suggest why this process is
more energetically favorable.
 (1 mark)

(iii) On what property of the transition metal does the catalysis depend?

(1 mark)
(TotalQ23= 16 marks)

24- (a) Define oxidation in terms of electron transfer.

(1 mark)

(b) State three properties which distinguish transition metals from main group metals.

(3 marks)

(c) Give the electronic configurations for Fe and for Fe3+ in the table below.

Suggest why Fe3+ is a more stable ion than Fe2+ under normal conditions.

_______________________________________________________________
(3 marks)

(d) (i) Name the types of reaction involved in the following changes:
 A to B ____________________________________________________

B to C ____________________________________________________
(2 marks)
(ii) Give the formula of compound B.

__________________________________________________________
(1 mark)
 (iii) Draw the structure of the ion responsible for the colour in solution C and show its shape.

(2 marks)

(e) Addition of aqueous copper(II) ions to aqueous iodide ions gives a precipitate of copper(I) iodide
and liberates iodine; the iodine can be titrated with aqueous sodium thiosulphate, so these
reactions form the basis for a volumetric analysis of copper, for example in metal alloys.

(i) Write an ionic equation for the reaction of copper(II)ions with iodide ions.

(ii) Given that the reaction of iodine with sodium thiosulphate is

I2(aq)+ 2S2O (aq) 2I (aq) + S4O (aq)

(1 mark)
-3
find the volume of sodium thiosuolphate solution of concentration 1.00mol dm needed to
react with the iodine liberated by copper ions from a brass screw of mass 2.00 g, containing
60% of copper by mass.

(3 marks)
(TotalQ24= 16 marks)
25- The hexagonal ring structure of benzene was first suggested by Kekulé in 1865, but the nature
of the bonding was not elucidated until the 1930s. This question concerns aspects of the
structure of benzene.

(a) The enthalpy of hydrogenation of cyclohexene to give cyclohexane is

–120 kJ mol–1

and that of cyclohexa-1,4-diene is –240 kJ mol–1 .

(i) What would you expect the value of the enthalpy of hydrogenation to be for the
hypothetical molecule cyclohexa-1,3,5-triene, on the basis of these data?

(1)
(ii) The hydrogenation enthalpy of benzene to give cyclohexane is
–208 kJ mol–1. Use your result from (i) and this information to draw an enthalpy level
diagram to show that benzene is thermodynamically more stable than the hypothetical
cyclohexa-1,3,5-triene. Label the stabilisation energy on your diagram.
 (iii) Explain in terms of bonding why benzene would be less reactive with bromine than
the hypothetical cyclohexa-1,3,5-triene.

(3)

(b) Ethanol, CH3CH2OH, and phenol, C6H5OH, both contain hydroxyl groups as their functional
group. However, they do not always react similarly.

(i) Write TWO equations to show one reaction of ethanol and one reaction of phenol
where they react in a similar manner.

(2)

(ii) Give an equation for a reaction of phenol which is not shown by ethanol.

(2)

(Total Q25=10 marks)

26-a Nitrobenzene can be prepared from benzene. Give the reagents and conditions and write the
equation for this reaction. Why must the temperature be controlled?

(5 marks)
b Benzene also reacts with ethanoyl chloride in a Friedel–Crafts reaction. Give the mechanism
for this reaction, including the production of the electrophile.

(4 marks)

c Phenol reacts with bromine water.

(i) Write the equation for this reaction

(1 mark)

(ii) Explain why this reaction does not need a catalyst and is much faster than the reaction
of bromine with benzene.

(3 marks)
Total 26= 13 marks
27- Some reactions of benzene are shown below.

(a) (i) Suggest the formula of reagent A in reaction 1.

(1)
...............................................................................................................................................................................................................................................

(ii) Write the equation to show how the catalyst, AlCl 3, reacts with reagent
A to
form the species which attacks the benzene ring.
(1)

(iii) Draw the structure of the intermediate ion formed when the species in
(ii)
attacks the benzene ring.
(1)
(b)The methylbenzene formed in reaction 1 generally reacts in a similar
way to
benzene but faster, as the ring is said to be activated.

(i) Explain how the presence of a methyl group activates the benzene
ring.
(1)
...............................................................................................................................................................................................................................................

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

(ii) Use your answer to (i) to explain why methylbenzene reacts faster.
(1)
...............................................................................................................................................................................................................................................

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

(c) (i) Draw the structural formula of compound X, formed in reaction 2.

(1)

(ii) The organic product of reaction 2 is also formed when the same
reactants, but
with an aluminium catalyst, are heated using microwave radiation.
Suggest
two reasons why this technique may be considered ‘greener’.

(2)
...............................................................................................................................................................................................................................................

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

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

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

(d) Name reagent B needed for reaction 3.

(1)
...............................................................................................................................................................................................................................................
 (Total for Question 27 = 9 marks)

28- Read the passage below carefully and answer the questions which
follow.
 (a) (i) Explain why Perkin’s attempted synthesis of quinine was almost
certain to fail.

(1)
.............................................................................................................................................................................................................................................
..

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

(ii) Suggest the effect that the growth of the organic chemicals industry in
the
 late19th century had on Holland and India in particular.

(2)
.............................................................................................................................................................................................................................................
..

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

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

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

(b) (i) What observation did Kekulé make to show that benzene does not
react
with bromine water? Explain the significance of this with reference to
his
representation of the molecule.
(2)
.............................................................................................................................................................................................................................................
..

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

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

(ii) Explain, in terms of the bonding in the benzene ring, why the
enthalpy of
hydrogenation is less exothermic than would be expected from a
molecule
with three double bonds.

(3)
.............................................................................................................................................................................................................................................
..

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

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

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

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

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

.............................................................................................................................................................................................................................................
..
 (Total for Question 28 = 8 marks)

29-Solid W is a blue salt containing a transition metal complex cation and one anion.

(a) Give the formulae of two different transition metal ions which can form blue
complex cations.

(2)
..........................................................................................................................................................

(b) Complete the following table.

(iii) Suggest two sources of the water which was given off when a pure dry sample
of W was heated.

(2)
...............................................................................................................................................................................................................................................

...............................................................................................................................................................................................................................................
(c) The following tests are carried out on separate portions of an aqueous solution of W.

Complete the table.

Note: in the third column, the formula of the ion, molecule or compound giving rise
to the observation is required.

(d) Suggest the formula of the complex cation in an aqueous solution of compound W.

(1)
.........................................................................................................................................................
...

(Total for Question 29 = 12 marks)

30- This question concerns the three isomers A, B and C, each of which has a relative molecular
mass of 134.

(a) The mass spectrum of substance A is shown below. Identify the species responsible for the
peaks labeled 1, 2 and 3.

Peak 1 .........................................................................................................................

Peak 2 .........................................................................................................................
 Peak 3 .........................................................................................................................

(3m)

(b) The infra-red spectra of two of these substances were also measured.

(i) Use the table and the spectra below to identify which spectrum is that of substance C.
The spectrum of substance C is spectrum number ..........................................
(1m)

(ii) Give one reason for your choice.

__________________________________________________________________________

__________________________________________________________________________
(1m)

(iii) Give one other reason why the other spectrum could not be that of substance C.

__________________________________________________________________________

__________________________________________________________________________

__________________________________________________________________________
(1m)

(Total for Question 30 = 6 marks)