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Revision Exercises Unit 5
Revision Exercises Unit 5
Chemistry
Revision Exercises
Unit 5
April 2010
July 2010 Gp B & C
Name:
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c) O22-
d) OF2
c) S2Cl2
d) H2SO3
5 Draw a labelled diagram of the apparatus that you would use to measure the standard reduction potential
of acidified potassium manganate(VII).
6 a) Calculate the standard cell potential and hence the thermodynamic feasibility of a reaction in which
manganate(VII) ions in acid solution oxidise ethanedioate ions to carbon dioxide, under standard
conditions at 25C.
2CO2(g) + 2eC2O42-(aq)
E = 0.49 V
+
2+
MnO4 (aq) + 8H (aq) + 5e
Mn (aq) + 4H2O(l)
E = +1.52 V
b) Suggest why, in practice, the reaction does not occur under standard conditions at 25C.
.
7 Explain how the potential of the standard hydrogen electrode would alter if the pressure of hydrogen gas
were to be increased.
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8 Refer to the Data Book (pg 14 16) and select:
a) the strongest oxidising agent
9 a) Calculate the cell potential for each of the following reactions and suggest whether or not the reaction
is feasible:
(i) a reaction between lead(IV) ions and chloride ions
b) Write equations for any of the reactions in (i)(iii) that are feasible.
10 Both potassium manganate(VII) and potassium dichromate(VI) are used in acid solution as oxidising
agents.
Use the data in Data Book to explain why hydrochloric acid must not be used in the oxidation of an
organic substance by potassium manganate(VII) but can be used when potassium dichromate(VI) is the
oxidising agent.
d) Predict the effect of increasing the pH of the solution on the feasibility of this disproportionation.
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12 Calculate Ecell for the oxidation by oxygen of iron in aqueous solution. Write the overall equation for this
reaction.
13 Explain why iron corrodes to a lesser extent in oxygenated water if the pH of the water is increased by
the addition of alkali.
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14 An empty crucible and its lid were weighed. Some metal carbonate, MCO3 was added and the crucible
and lid were reweighed. The crucible was then heated until there was no further loss in mass. The
carbonate decomposed according to the equation:
MCO3 MO + CO2
The mass of the carbonate was 1.51 g; the mass of the oxide was 0.93g.
a) Calculate the mass of carbon dioxide produced,
b) Calculate the amount (in moles) of carbon dioxide and hence the molar mass of the metal carbonate.
c) Calculate the relative atomic mass of the metal M and suggest its identity.
d) Assume that there is a possible error of 0.01 g in each weighing, calculate the percentage error in
the molar mass of MCO3.
e) Calculate the possible maximum and minimum values of the molar mass of MCO3 and hence of the
relative atomic mass of M.
f) Comment on the reliability of the identity of M that you suggested in part c).
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g) How might the experiment be improved to give a more reliable identification of the metal?
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15 a) Predict whether ferrate(VI) ions, FeO42-, will be reduced to Fe3+ or to Fe2+ ions by hydrogen peroxide
in an acidic solution.
FeO42-(aq) + 8H+(aq) + 3eFe3+(aq) + eO2(g) + 2H+(aq) + 2e-
Fe2+(aq)
Fe3+(aq) + 4H2O(l)
E = +2.20 V
E = +0.77 V
H2O2(aq)
E = +0.68 V
b) Write the overall equation for the reaction that takes place.
16 25.00 cm3 of a solution of potassium iodate(V) was pipetted into a conical flask. 25 cm3 of dilute sulfuric
acid and 2 g of potassium iodide (an excess) were added. The iodine liberated was titrated with 0.104
mol dm-3 sodium thiosulfate solution using starch as an indicator. The mean titre was 23.20 cm3.
Calculate the concentration of the potassium iodate(V) solution.
17 Describe how the concentration of a solution of sodium chlorate(I), NaClO, could be found
experimentally.
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18 What are the advantages and disadvantages of running a motor vehicle using a fuel cell that is powered
by hydrogen?
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19 Discuss the advantages and disadvantages of a breathlyser that uses potassium dichromate and a
breathlyser that uses a fuel cell.
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20 Explain why the strong OH bond stretching vibration in ethanol cannot be used in infrared
breathlysers.
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21 Iron(II) sulfate contains water of crystallization and its formula can be written as FeSO4.xH2O.
Describe an experiment that would enable you to find the value of x. The method must involve a
titration.
Your answer should include what you would do, what measurements you would make and show how
you would use your to calculate the value of x.
(Heating the hydrated solid would decompose the iron(II) sulfate, so this is not an acceptable method.)
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22 Search the internet to find details of the composition of rechargeable lithium cells that are used in
cameras and camcorders.
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1s2 _________________________
3 Explain why the first ionisation energies of the p-block elements increase considerably from left to right
whereas those of the d-block elements hardly alter.
4 Explain why the melting point of titanium is higher than that of calcium.
6 Explain why titanium can form both 2+ and 3+ ions whereas calcium and zinc do not form 3+ ions.
..
7 Write equations for the reactions, if any, of dilute hydrochloric acid and of aqueous sodium hydroxide
with:
a) iron(III) oxide, Fe2O3
b) iron(VI) oxide, FeO3
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8 Draw a diagram of the [Cr(H2O)6]3+ ion to show its shape. Mark on your diagram the bond angles. Name
the types of bond in the ion and say where in the structure these bonds occur.
.
13 Explain why hydrated Ti4+ ions are colourless. but hydrated Ti3+ ions are coloured.
14 explain why, when excess ammonia is added to copper(II) sulfate solution, the colour changes from
turquoise (blue-green) to violet-blue.
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16 Why is anhydrous copper(II) sulfate white and why are copper(I) complexes also white?
17 State what you would see, and write the equations for, the reactions of sodium hydroxide and of
ammonia solution with:
a) a solution of nickel(II) ions
18 When sodium hydroxide solution is added to a solution of iron (II) ions, a green precipitate is produced.
When hydrogen peroxide solution is then added, the precipitate turns red-brown. Identify the green and
red-brown precipitates and explain what is happening in the two reactions.
19 Hydrated chromium(III) ions can be deprotonated. Write equations to show the deprotonation that takes
place when:
a) the hydrated ions are dissolved in water
b) sodium hydroxide is added to the hydrated ions, slowly and then in excess
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21 A 25.0 cm3 sample of a 0.100 mol dm-3 solution of V3+ ions was placed in a conical flask and excess
dilute sulfuric acid added. Potassium manganate(VII) of concentration 0.0500 mol dm-3 was added from
a burette until a taint pink colour was seen. The titre was 20.0 cm3.
a) Calculate the amount (moles) of potassium manganate(VII) ions in the titre.
b) Calculate the number of moles of electrons that the manganate(VII) has received from the
vanadium(III) ions.
d) Calculate the oxidation state of the vanadium after reaction with potassium manganate(VII).
Use the E values in the Data Book for the following questions
22 a) Predict whether hydrogen sulfide will reduce VO2+ ions to VO2+ or V3+ ions.
b) Write the overall equation for the reaction that takes place.
23 a) Predict the oxidation state of vanadium when oxygen gas is blown through an acidified solution of V2+
ions.
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b) Write the equation for the overall reaction that takes place.
24 a) Predict whether iodine will oxidise V3+ ions to VO2+ or to VO2+ or not react at all.
25 Predict whether chloride and bromide ions will be oxidised by manganese(IV) oxide, MnO2, in acid
solution.
26 The reduction potential for Cr2+ ions being reduced to chromium metal is 0.91 V and that for Cr3+ ions
being reduced to Cr2+ ions is 0.41 V:
Cr2+ + e-
Cr
E = 0.91 V
Cr3+ + e-
Cr2+
E = 0.41 V
Predict whether Cr2+ ions will disproportionate in aqueous solution to Cr metal and Cr3+ ions. If so, write
the equation for the reaction that takes place.
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b) a solution containing chromate(VI) ions
b) heterogeneous catalyst
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c) Hence, draw a labelled energy-level diagram showing both the formation of cyclohexatriene and
benzene from solid carbon and hydrogen gas and the resonance stabilisation energy.
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b) C6H4BrNO2
6 Write equations for the production of the electrophiles for the following reactions of aromatic compounds:
a) nitration
b) bromination
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c) alkylation
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7 Write the mechanism, including the production of the electrophile, of the reaction of benzene with
ethanoyl chloride.
8 Write equations and state the conditions for the reactions of methylbenzene with:
a) ethanoyl chloride
.
b) bromine
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c) nitric acid
.
9 Explain why phenol
a) is a stronger acid than ethanol
10 Write the structural formulae of the organic products, if any, of attempting to react phenol with:
a) aqueous potassium hydroxide
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b) chlorine water
11 Calculate the pH of a 0.20 mol dm-3 solution phenol, Ka = 1.3 x l0-10 mol dm-3.
12 Calculate:
a) the mass of bromine that would react with 1.23 g of phenol
14 Draw a diagram to show how two molecules of benzoic acid are hydrogen bonded. Mark in the bond
angles around the hydrogen bond.
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16 Write the mechanism, including the formation of the electrophile, of the nitration of methylbenzene.
17 An organic compound X burns with a smoky flame. It gives an orange precipitate with Bradys reagent
but does not form a silver mirror with Tollens reagent. It gives a yellow precipitate when warmed gently
with a solution of iodine and sodium hydroxide. Draw the structural formula of a compound that could be
X.
18 Search the internet and write a brief account of the discovery in the nineteenth century of phenol
(carbolic acid) and its use as an antiseptic by the surgeon Joseph Lister.
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2 C4H11N has several structural isomers. Write the structural formula of the isomer of C4H11N that is:
a) a primary amine with a branched chain
d) a tertiary amine
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5 Explain why ethylamine is soluble in water but chloroethane and ethane are both insoluble.
6 Explain why ethanoic acid, CH3COOH, has a higher boiling point than 1-propylamine, CH3CH2CH2NH2,
and why both these compounds have a higher boiling point than butane, CH3CH2CH2CH3.
7 Ethylamine, C2H5NH2, can be prepared from ethanoic acid by a three-step synthesis. Outline this process.
8 An organic compound contains 39.3% carbon, 11.5% hydrogen, 26.2% oxygen and 23.0% nitrogen by
mass.
a) Calculate its empirical formula.
b) The molecular formula of this compound is the same as its empirical formula. It reacts with
phosphorus pentachloride, giving off misty fumes. Suggest a structural formula for this compound.
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b) ethanoyl chloride
c) iodomethane
10 Explain why methylamine is a stronger base than ammonia which itself is a stronger base than
phenylamine.
11 Explain why aminoethanoic acid is a solid at room temperature and is soluble in water.
12 Ethylamine has a distinctive smell. When some dilute hydrochloric acid is added, the smell disappears.
If aqueous sodium hydroxide is now added in excess, the smell returns. Write equations for the
reactions involved.
14 Phenylamine and chlorobenzene are equally polar molecules. Phenylamine boils at 184C;
chlorobenzene boils at 132C. Phenylamine is slightly soluble in water and forms a clear solution when
dilute hydrochloric acid is added. Chlorobenzene is immiscible with both water and dilute hydrochloric
acid.
Explain:
a) the difference in boiling temperatures of the two substances
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b) ethanoyl chloride
16 When phenylamine is treated with an acidified solution of sodium nitrite at a temperature between 0C
and 10C, benzenediazonium ions are formed. Explain why the temperature must not
a) drop below 0C
.
19 Write the equation for the formation of the polymer made from 1,5-pentanedioic acid and
diaminoethane.
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20 Explain why a polyamide such as Terylene has a higher melting temperature than an addition polymer
such as poly(propene).
22 The formula of all naturally occurring amino acids can be written as NH2CHRCOOH.
a) Rewrite this formula as the zwitterion.
b) Write an equation for the reaction of the zwitterion with aqueous acid.
c) Write an equation for the reaction of the zwitterion with aqueous alkali.
23 Draw the two optical isomers of aminobutane-1,4-dioic acid. Identify which of the two is aspartic acid.
24 Write the structure of a dipeptide formed from aminoethanoic acid and 2-amino- propanoic acid.
26
Draw a diagram of a uracil molecule in one strand of mRNA when hydrogen-bonded to an adenine
molecule in a strand of DNA .
The information needed for questions 2629 is not found in this textbook. You are advised to do your
own research to find answers to these questions. Possible sources are the internet, biology textbooks
and other students who are studying biochemistry.
26 Explain the link between a DNA molecule, an mRNA molecule and the polypeptide formed. What is the
sequence of bases needed to put a leucine residue in a polypeptide?
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Write brief notes on the discoveries about DNA structure made by Wilkins and Franklin in London and
Crick and Watson in Cambridge.
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3 Spearmint oil contains the compound carvone. Use the results of the following tests that were carried out
on carvone to deduce the functional groups present in the molecule. Justify your deductions from each
test.
a) It turned brown bromine water colourless.
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5 This question concerns citral, C10H16O (found in lemon grass oil) and geraniol, C10H18O (found in rose oil).
a) Describe a test to show that citral is an aldehyde.
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d) In what way would the infrared spectra of citral and geraniol differ?
6 Compound Z has the following composition by mass: carbon, 55.8 %; hydrogen, 7.0%; oxygen, 37.2%.
a) Calculate the empirical formula of compound Z.
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7 An ester E has the molecular formula C7H14O2. When heated under reflux with aqueous sodium
hydroxide,
followed by the addition of excess acid, it was converted into two compounds F and G:
Compound F has the following composition by mass: carbon, 54.5%; oxygen, 36.4%; hydrogen, 9.1%.
Compound F gives off carbon dioxide when added to a solution of sodium hydrogen- carbonate.
Compound F has three peaks in its NMR spectrum.
Compound G does not give a precipitate with iodine and sodium hydroxide.
Deduce the structural formula of the ester E and write the equation for its reaction with sodium
hydroxide.
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8 When phenylamine reacts with ethanoyl chloride, a solid is formed that is soluble in hot water but
insoluble in cold water. Describe how you could purify this solid.
9 Cyclohexanol (boiling point 161C) can be converted into cyclohexanone (boiling point 156C).
a) State the reagents and conditions for this reaction.
b) State how you would obtain a pure sample of cyclohexanone from a mixture containing it and 2%
cyclohexanol.
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c) State how you would obtain a pure sample of cyclohexanone from a mixture containing it and 25%
cyclohexanol.
10 Before cyclohexanone and cyclohexanol (produced as in question 9) can be separated, the organic
substances, which are insoluble in water, have to be extracted from the reaction mixture.
a) Describe how this would be achieved.
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c) How would you know when the water removal was complete?
11 An organic compound Z contains carbon, hydrogen and oxygen only. When 4.85g of Z was burnt in
excess oxygen 11.9 g of carbon dioxide and 4.85g of water were produced.
The mass spectrum of Z had a peak due to its molecular ion at a mass/charge ratio of 72. Compound Z
gave a yellow precipitate with Bradys solution but no precipitate with iodine and sodium hydroxide
solution. Its NMR spectrum had four peaks in the ratio 3:2:2:1.
Showing all your working and using all the data provided, deduce the structural formula of Z.
12 a) Give the reagents, conditions and intermediates in the conversion of but-2-ene to 3-aminobutan-2one, CH3COCH(NH2)CH3.
.........................................................................................................................................................
b) Explain what effect the product would have on the plane of polarisation of plane-polarised light.
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with the following (you may assume that the functional groups behave independently):
a) phosphorus pentachloride
b) sodium hydrogencarbonate
d) 2,4-dinitrophenylhydrazine
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14 Give the reagents, conditions and intermediates in the conversion of ethanol to ethanoyl chloride.
.
15 A compound C4H8O2 was tested as follows:
It did not give a precipitate with Bradys reagent.
It turned bromine water from brown to colourless.
When excess PCl5 was added, 2 mol of HCl was given off per mol of the organic compound.
The compound had three peaks in its NMR spectrum and a peak at m/e = 57 in its mass spectrum,
Suggest a formula for the compound. Justify your answer
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17 A student wished to convert propan-1-ol into 1-bromopropane. Two different methods were suggested:
(i) Heat the alcohol under reflux with a mixture of solid potassium bromide and concentrated sulfuric acid
(ii) Heat the alcohol under reflux with a mixture of solid potassium bromide and concentrated phosphoric
acid.
Both methods initially produce gaseous hydrogen bromide. This then reacts with the alcohol to form the
bromoalkane which is distilled off and condensed.
The hazards were identified as:
concentrated sulfuric acid: corrosive and an oxidising agent
concentrated phosphoric acid: corrosive
hydrogen bromide vapour: irritant and a reducing agent
propan-1-ol and 1-bromopropane: volatile and flammable
bromine: volatile and irritant vapour
a) Explain which method should be used to minimise the risk.
b) For the method selected in a, suggest suitable special safety precautions that should be taken to
minimise the risk
18 a) Outline how you would convert C6H5CH=CHCH3 into the following compound,
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b) Identify the product formed by reacting compound M with iodine and sodium hydroxide.
19 12.6 g of benzene was nitrated and the nitrobenzene produced was reduced with tin and concentrated
hydrochloric acid. After addition of sodium hydroxide, the phenylamine was steam-distilled out of the
reaction mixture, washed, dried and redistilled. The mass of pure phenylamine produced was 6.75g.
Calculate the percentage yield.
20 It was required to prepare the compound (CH3)2C(OH)CONH2 from propanone. A student suggested the
following outline synthesis:
Explain why this sequence would not give the required product.
21 Explain why the addition of hydrogen cyanide, HCN, to butanone, CH3COC2H5, gives a racemic mixture,
rather than a single optical isomer.
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22 The rate equation for the nucleophilic substitution reaction of a single optical isomer of the
halogenoalkane, 1-fluoro-1-iodoethane, CH3CHFI, with cyanide ions is:
rate = k[CH3CHFI][CN-]
a) Use this information to explain whether the product would be a single optical isomer or the racemic
mixture.
23 This question is about the combinatorial reaction between two hydroxyacid chlorides, HORCOCl and
HORCOCl. Each was separately adsorbed onto resin beads through the OH group. The results
were mixed and divided into two portions. One sample was then reacted with HORCOCl and the other
with HORCOCl. The results of these reactions were mixed and divided again; one portion was reacted
with HORCOCl and the other with HORCOCl. This was repeated twice more. How many different
polyester compounds were produced?
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