Alcohols Questions Part 1: Answer three of the following questions (1 – 4).

1. Cyclohexene, C6H10, can be prepared from cyclohexanol, C6H11OH, by the dehydration method described
below.
A reaction mixture of 5.0 g of cyclohexanol and 3.0 cm3 of concentrated sulfuric acid, H2SO4, was placed
in a round-bottomed flask and the apparatus arranged for distillation is shown below. An impure liquid,
consisting of two immiscible layers, was collected after distillation.

The upper organic layer was separated and dried. Finally it was re-distilled to yield 1.8 g of cyclohexene.
The equation for the preparation is shown below.

a. i. What is the relative molecular mass of cyclohexanol? [1]

ii. How many moles of cyclohexanol were used in the experiment? [1]
iii. Calculate the percentage yield of cyclohexene in the experiment.
Give your answer to two significant figures. [3]

b. i. A chemical test could have been used to show that an alcohol was present.
State the reagent and the expected observation. [2]
ii. Draw the structure of the organic product that would have been form in (b. i) if cyclohexanol
was the alcohol. [1]

2. This question is about the six alcohols below.

a. Which alcohol is an example of a tertiary alcohol? [1]

b. Draw the skeletal formula for 2-methylpentan-3-ol. [1]
c. Butan-2-ol and 2-methylpropan-2-ol are structural isomers.
i. What is meant by the term structural isomer? [1]
ii. Draw another structural isomer of these two alcohols. [1]
d. Ethane-1,2-diol can be dissolved in water to act as an anti-freeze in car radiators.
Explain why ethane-1,2-diol is very soluble in water. [2]
e. Butan-2-ol is heated with H2SO4 catalyst.
 A mixture of three alkenes forms, B, C, and D.
 The alkenes B and C are stereoisomers.
i. Draw the structures of the two stereoisomers B and C. [2]
ii. What type of stereoisomerism is shown by B and C? [1]
iii. Draw the structure of the other alkene, D, that is formed in this reaction. [1]
3. There are four structural isomers of C4H10O that are alcohols.
a. Alcohols can be classified as either primary, secondary or tertiary.
Draw, name and classify each of the four structural isomers of C4H10O by completing the boxes in
the table below. Some have been completed for you. [6]

b. Which structural isomer of C4H10O that can be oxidised to form butanone. [1]
c. Alcohols such as butan-1-ol have high boiling points due to the presence of hydrogen bonds.
Draw two molecules of butan-1-ol linked by a hydrogen bond. Include any relevant dipoles and lone
pairs of electrons. [3]

4. Menthol is a naturally occurring cyclic alcohol found in peppermint oil. It has been used in throat sprays
and cough drops for many years. The skeletal formula of menthol is shown below.

a. i. What is the molecular formula of menthol? [1]

ii. Classify menthol as a primary, secondary or tertiary alcohol. [1]
b. The reaction scheme below shows some of the reagents and conditions needed to convert menthol
into three organic compounds H, I and K.

Draw compounds H and I. [1]

c. Menthol can be oxidised to form compound K.
i. State the reagents and conditions. [2]
ii. State what you would see during the oxidation. [1]
iii. Write a balanced equation, using skeletal formulae, for the oxidation.
Use [O] to represent the oxidising agent. [1]
Alcohols Questions Part 2: Answer all of the final question (5).

5. The alcohols are an example of an homologous series.

The table shows the boiling points for the first four members of straight-chain alcohols.

a. i. What is the general formula of a member of the alcohol homologous series? [1]
ii. Deduce the molecular formula of the alcohol that has 13 carbon atoms per molecule. [1]
b. Alcohols contain the hydroxyl functional group.
What is meant by the term functional group? [2]
c. At room temperature and pressure, the first four members of the alcohol homologous series are
liquids whereas the first four members of the alkanes homologous series are gases.
i. Explain this difference. [3]
ii. Methylpropan-1-ol and butan-1-ol are structural isomers. Methylpropan-1-ol has a lower boiling
point that butan-1-ol.
Suggest why. [2]
d. Alcohols, such as methanol, can be used as fuels.
i. Write equations for the complete and incomplete combustion of methanol. [2]
ii. Suggest what conditions might lead to incomplete combustion of methanol. [1]
e. Butan-1-ol can be oxidised.
Write an equation for the reaction that takes place.
Use [O] to represent the oxidising agent. [2]
Haloalkanes Questions Part 1:

1. This question is about halogenoalkanes A to D, shown below.

*
a. Answer the questions that follow by using the appropriate letter A, B, C or D.
Each letter may be used once, more than once or not at all.
i. Which is 2-chloro-2-methylpropane? [1]
ii. Which could react with hot aqueous sodium hydroxide to produce butan-2-ol? [1]
iii. Which could react with hot aqueous sodium hydroxide to produce a tertiary alcohol? [1]
iv. Which two could react with hot ethanolic sodium hydroxide to produce but-1-ene? [1]
b. Compound A can react with aqueous hydroxide ions, OH–. The hydroxide ion is a nucleophile.
i. Define the term nucleophile. [1]
ii. Complete, with the aid of curly arrows, the mechanism involved in this reaction. [3]
2. Halogenoalkanes are polar molecules that react with nucleophiles.
a. The displayed formula of chloromethane is shown below. Label the dipole on the C–Cl bond and
state the value of the H–C–Cl bond angle. [2]

b. Chloromethane reacts with ammonia in a nucleophilic substitution reaction.

Part of the mechanism for this reaction is shown below.

i. What is meant by the term nucleophile? [1]

ii. Add ‘curly arrows’ to step 1 of the mechanism to show the movement of electron pairs. [2]
iii. Deduce a balanced equation for the overall reactions. [1]
c. Ammonia was reacted with iodomenthane rather than with chloromethane.
What would happen to the rate of reaction? Explain your answer. [2]
Haloalkanes Questions Part 2: Answer all the following questions (3-5).

3. Poly(tetrafluoroethene), PTFE, and poly(chloroethene), PVC, are halogenated plastics.

a. Write an equation, using displayed formulae, for the reaction to form PTFE from its monomer. [3]
b. The combustion of waste polymers can be used for energy production.
What problem is caused by disposing of PTFE and PVC in this way? [1]

4. A student carried out an investigation to compare the rates of hydrolysis of 1-iodoproane and 1-
bromopropane. The student found that 1-iodopropane was hydrolysed faster.
The equation for the reaction with 1-iodopropane is shown below.
CH3CH2CH2I + OH–  CH3CH2CH2OH + I–
a. i. Outline the mechanism for this hydrolysis of 1-iodopropane.
Show curly arrows and relevant dipoles. [3]
ii. State the name of this type of mechanism. [1]
b. Explain why 1-iodopropane is hydrolysed faster than 1-bromopropane. [2]
c. Chlorofluoroalkanes, CFCs, were developed from flouroalkanes and were used in aerosols and as
refrigerants. Under the Montreal Protocol, CFCs are now largely banned because of their ozone-
depleting properties. CFCs have now been replaced in many applications.
Suggest two reasons why there is still concern about ozone depletion. [2]
d. Fluoroalkenes are used to make polymers. For example, PVF, (CH2CHF)n, is used to make non-
flammable interiors of aircraft.
i. Draw two repeat units of the polymer PVF showing all bonds. [1]
ii. Draw the structure of the monomer of PVF. [1]
e. Once polymers have been used, they become waste.
Outline two ways that waste polymers are processed usefully, rather than just dumped in landfill
sites. [2]

5. NO is a radical and contributes towards ozone depletion in the stratosphere.

a. What is a radical? [1]
b. One of the processes leading to the breakdown of ozone in the stratosphere can be represented by
the following two equations.
NO(g) + O3(g)  NO2(g) + O2(g)
NO2(g) + O(g)  NO(g) + O2(g)
What is the role of NO in this process? [1]
c. Ozone in the stratosphere is broken down to make O2 and O.
Describe and explain how the concentration of ozone in the stratosphere is maintained. [2]
d. Why is it important to life on the Earth’s surface that the concentration of ozone in the stratosphere
is maintained? [1]
e. Research chemists have proposed possible reduction mechanisms for ozone depletion caused by
chlorine radicals. The equations below represent part of such a mechanism.

i. Complete the equations. [2]

ii. Write an equation for the overall reaction in (i). [1]
Haloalkanes Questions Part 3:

The following questions are all long prose, so there will be an additional mark for each question for the
quality of written communication.

6. A student investigates the rate of hydrolysis of six halogenoalkanes.

The student mixes 5 cm3 of ethanol and five drops of halogenoalkane. This mixture is warmed to 50 oC
in a water bath. The student adds 5 cm3 of aqueous silver nitrate, also heated to 50 oC, to the
halogenoalkane. The time taken for a precipitate to form is recorded in a results table.
The student repeats the whole experiment at 60 oC instead of 50 oC.

Describe and explain factors that affect the rate of hydrolysis of halogenoalkanes.
Include ideas about:
 The halogen in the halogenoalkanes.
 The groups attached to the carbon of the carbon-halogen bond (the type of halogenoalkane).
 The temperature of hydrolysis.
In your answer you should link evidence with your explanation. [7]

7. The rates of hydrolysis of 1-chloropentane, 1-bromopentane and 1-iodopentane are different.

 Briefly outline how you would compare the reaction rates.
 Explain why 1-chloropentane, 1-bromopentane and 1-iodopentane react at different rates and
state the order of reactivity.
 Use suitable equations in your answer. [8]
Synthesis Questions: Answer all questions (1 – 5).

1. Prop-2-en-1-ol, CH2=CHCH2OH is a colourless liquid with a pungent smell. It is produced in industry to

make resins, plasticisers and many other chemicals.
a. The reaction scheme below shows how prop-2-en-1-ol can be used for the production of a variety of
chemicals.

State the reagent(s) and catalyst, if any, for each of reactions 1, 2 and 3.
i. Reaction 1. [2]
ii. Reaction 2 [2]
iii. Reaction 3 [1]
b. CH2=CHCH2OH also reacts with bromine to form CH2BrCHBrCH2OH.
Describe, with the aid of curly arrows, the mechanisms involved. Show any relevant dipoles. [4]
c. Prop-2-en-1-ol polymerises rapidly.
i. Show three repeat units and draw a circle around one repeat unit. [2]
ii. Write a balanced equation for this polymerisation. [2]
iii. Name the polymer. [1]
d. The products from reactions 1 and 2 are CH3CH2CH2OH and CH3CH(OH)CH2OH, respectively. Both
undergo oxidation reactions with acidified dichromate ions, H+/Cr2O72–.
i. Write a balanced equation for the reaction of CH3CH2CH2OH with excess H+/Cr2O72– under reflux.
Use [O] to represent the oxidising mixture. [2]
+ 2–
ii. When CH3CH(OH)CH2OH is oxidised with H /Cr2O7 it produces a mixture of organic products,
one of which is shown below.

Suggest the structure of two other possible oxidation products from this reaction. [2]
2. Alkenes are unsaturated hydrocarbons used in the industrial production of many organic compounds.
a. Complete the flowchart below to show the organic product formed in each addition reaction of
methylpropene. [4]

b. Curly arrows are used in reaction mechanisms to show the movement of electron pairs during
chemical reactions.
Use curly arrows to outline the mechanism for the addition reaction of methylpropene with
bromine.
Include relevant dipoles in your answer. [4]
c. Alkenes can be prepared from the dehydration of alcohols with an acid catalyst.
Cyclohexene can be prepared by the dehydration of cyclohexanol, shown below.

A student reacted 7.65 g of cyclohexanol, C6H12O, and obtained 0.0268 mol of cyclohexene.
i. What is the molecular formula of cyclohexene? [1]
ii. Calculate the percentage yield of cyclohexene. [3]
d. Percentage yield has been used for many years to measure the ‘success’ of a reaction.
Recently, chemists have turned their thoughts also to the atom economy of a reaction.
i. Explain the term atom economy. [1]
ii. Cyclohexene can also be prepared by the reaction below.

Explain why the atom economy of this cyclohexene preparation is higher than that from
cyclohexanol in (c). [2]
3. Alcohols are used in the industrial production of many organic compounds.
a. Complete the flowchart below to show the organic product formed in each of the reactions of
butan-1-ol. [4]

b. Butan-1-ol can be prepared by the alkaline hydrolysis of 1-iodobutane.

CH3CH2CH2CH2I + OH–  CH3CH2CH2CH2OH + I–
The reaction mixture is gently heated for 20 minutes.
i. The curly arrows model is used in reaction mechanisms to show the movement of electron pairs.
Use the curly arrow model to outline the mechanism for the alkaline hydrolysis of 1-iodobutane.
In you answer, include the name of the mechanism, the type of bond fission and relevant
dipoles. [5]
ii. A student decides to prepare butan-1-ol by the alkaline hydrolysis of 1-chlorobutane.
Suggest, with reasons, any change in the conditions from those used in the alkaline hydrolysis of
1-iodobutane. [2]
4. The flowchart below shows some of the organic compounds that could be made starting from
cyclohexane.

a. Explain why cyclohexene is described as unsaturated and as a hydrocarbon. [2]

b. The reaction between chlorine and cyclohexane is an example of radical substitution.
State one problem of using this reaction to prepare a sample of chlorocyclohexane. [1]
c. The formation of cyclohexanol from chlorocyclohexane involves the reaction of a nucleophile, the
hydroxide ion.
Suggest what feature of the hydroxide ion makes it able to act as a nucleophile. [1]
d. Using the flowchart, draw the structures of compound A and compound B. [2]
e. Describe, using the ‘curly arrow model’, the mechanism for the reaction between Br 2 and
cyclohexene.
Show relevant dipoles and charges. [4]
5. This question is about the following organic compounds.

You will have to refer to these compounds throughout the question.

a. Explain why compound A is a hydrocarbon. [1]
b. Which compound is a saturated hydrocarbon? [1]
c. What is the molecular formula for compound E? [1]
d. Which compounds are structural isomers of one another? [1]
e. In compound G, there are different shapes around different carbon atoms.
i. State and explain the shape around carbon atom number 1 in compound G. [2]
ii. State the shape around carbon atom number 2 in compound G. [1]
f. i. Which compound shows E/Z isomerism? [1]
ii. Explain why some molecules show E/Z isomerism. [2]
g. Compounds B and C are halogenoalkanes. Both compounds can be hydrolysed with aqueous
potassium hydroxide, KOH(aq).

Describe and explain the hydrolysis of B and C.

In your answer, include:
 One equation including the structure of the organic product.
 The reaction mechanism, using the curly arrow model, showing any relevant dipoles.
 The type of bond fission that occurs.
 The reasons for the difference in the rate of hydrolysis.
Your answer needs to be clear and well organised using the correct terminology. [10]
h. Compound A is 1-methylcyclohex-1-ene.
Compound A reacts with H2 to give one product and with HBr to give two products.
Draw the structures of the products of these reactions. [3]
Analysis Questions Part 1: Answer all questions (1 – 4).

1. Mass spectrometry is an important analytical technique. It can be used to distinguish between the
isomers 1-bromopropane, CH3CH2CH2Br, and 2-bromopropane, CH3CHBrCH3.
a. The relative molecular mass of 2 bromopropane is 123.
The mass spectrum of 2-bromopropane contains peaks at m/z 122 and 124.
i. Identify the ion responsible for the two peaks. [2]
ii. What are the relative heights of the peaks at m/z 122 and 124.
b. Mass spectra can be used to distinguish between 1-bromopropane and 2-bromopropane.
Deduce the m/z value of a peak that would be found in the mass spectrum of 1-bromopropane but
not in the mass spectrum of 2-bromopropane. [1]

2. There is much international concern that an increase in atmospheric concentrations of carbon dioxide
and methane may lead to global warming and climate change as they are both greenhouse gases.
a. What type of radiation is absorbed by methane molecules and what effect does this radiation have
on these molecules. [2]
b. Some scientists are more concerned about carbon dioxide as greenhouse gas than methane.
Suggest why. [1]

3. Butan-1-ol was oxidised using acidified potassium dichromate. The organic product was analysed by
infra-red spectroscopy. The infra-red spectrum obtained is shown below.

a. Use the spectrum to identify the organic product. Explain your reasoning. [3]
b. Write a balanced equation for this oxidation. Use [O] to represent the oxidising agent. [2]
4. Alcohols A, B, C and D are shown below.

A student heated each alcohol, A-D, with acidified potassium dichromate (VI) as the oxidising agent.
With alcohols A, B and C, the colour turned from orange to green.
a. Identify the organic product and write a balanced equation for the reaction of alcohol B with
acidified potassium dichromate (VI).
Use [O] to represent the oxidising agent, acidified potassium dichromate (IV). [2]
b. The organic product obtained from C was analysed by infrared (IR) spectroscopy.
The IR spectrum of the product is shown below.

Identify the organic product. Explain your reasoning. [3]

Analysis Questions Part 2: Answer five of the following questions (5 – 11).

5. A chemistry student was interested in aromatherapy and decided to investigate rose oil which can be
extracted from both the flowers and the leaves of roses.
a. The student separated an organic liquid, compound A, from rose oil. Compound A has a relative
molecular mass of 154 and contains 77.9% C, 11.7% H and 10.4% O by mass.
Calculate the molecular formula of compound A. [3]
b. The student reacted compound A with bromine and observed that the bromine was decolourised.
i. What conclusion can be drawn from this observation? [1]
ii. Further investigation revealed that 0.0100 mol of compound A reacted exactly with 3.196 g of
bromine.
Calculate the number of moles of bromine, Br2, that reacted. [2]
iii. What conclusion could the student draw about compound A from this investigation? [1]
c. The student analysed the infra-red spectrum of compound A and concluded that the compound is
an alcohol.
On the infra-red spectrum below label, with a letter X, the absorption confirms that compound A is
an alcohol. [1]

d. After careful research the student concluded that A was one of the three compounds below.

The student heated compound A with acidified potassium dichromate and the orange colour did
not turn green. The student was therefore able to identify compound A as one of the three
compounds shown above.
State what compound A is and explain your reasoning. [2]
e. Suggest a reagent that would react with the alcohol group in compound A to produce a gas.
State the reagent and identify the gas and the organic product. [3]
6. Compound A contains carbon and hydrogen only. The mass spectrum of A is shown below.

a. The ratio of the M : (M + 1) peaks is 29.1 : 3.2.

i. What is responsible for the M + 1 peak. [1]
ii. Determine the number of carbon atoms in compound A. [2]
iii. Deduce the molecular formula for compound A. Show your working. [3]
iv. Suggest the ion responsible for peak X. [1]
Compounds B, C and D are all isomers, each with the molecular formula C4H8O2.

b. In the mass spectra of the three compounds, identify:

i. An ion which could cause a peak in all three spectra. [1]
ii. An ion which could cause a peak in the mass spectra of C and D but not of B. [1]
c. Infra-red spectroscopy could be used to distinguish between compounds B, C and D.
The infra-red spectrum of one of the three isomers is shown below.

Identify the isomer. Explain your reasoning. [2]

7. In this question, you are asked to suggest structures for several organic compounds.
a. Compounds F, G and H are unbranched alkenes that are isomers, each with a relative molecular
mass of 70.0.
Compounds F and G are E/Z stereoisomers.
Compound H is a structural isomer of compounds F and G.
 Explain what is meant by the terms structural isomer and stereoisomer.
 Explain why some alkenes have E/Z isomerism.
 Analyse this information to suggest possible structures for compounds F, G and H.
In your answer you should make clear how each structure fits with the information given above. [11]
b. An analytical chemist was provided with compound J which has an unbranched carbon skeleton.
After analysis, the chemist obtained the following results.

Use this information to suggest all the possible structures for the unbranched compound J.
In your answer you should make clear how your explanation is linked to the evidence. [8]
8. Alcohol E is one of the following alcohols.

A student oxidises alcohol E by heating under reflux with excess acidified potassium dichromate (VI). An
organic product F is isolated.
The mass spectrum of alcohol E is shown below.

The infrared spectrum of the organic product F is shown below.

 Name or draw the structures of the alcohol E and the organic product F.
 Write an equation for the reaction of alcohol E with acidified potassium dichromate (VI).
Use [O] to represent the oxidising agent, acidified potassium dichromate (VI).
In your answer, you should make clear how each structure fits with the information given above. [7]
9. Infrared spectroscopy and mass spectroscopy are used to identify substances.
a. Police use breathalysers to detect ethanol in the breath of drivers.
i. Some modern breathalysers use infrared spectroscopy.
Suggest two characteristic infrared absorption that could be used to identify the presence of
ethanol vapour. [2]
ii. Some older breathalysers use the redox reaction between acidified dichromate(VI) ions and
ethanol. A colour change was seen which indicated the presence of ethanol in the breath.
What is the colour change that would be seen in this breathalyser if ethanol was present in the
breath? [1]
iii. Give an equation to show the reaction between acidified dichromate (VI) ions and ethanol.
Use [O] to represent the acidified dichromate (VI) ions, the oxidising agent. [2]
b. Infrared spectroscopy and mass spectrometry are used in the search for organic molecules in outer
space.
Compound A has been analysed by infrared spectroscopy.

The mass spectrum of compound A is shown below.

i. A research chemist concludes that compound A is a hydrocarbon.

What evidence is there to support this conclusion? [2]
ii. How does the mass spectrum confirm that compound A has a molecular formula of C4H10? [1]
iii. Draw the structural isomers of C4H10. [1]
iv. Identify the fragment ions that give rise to the following peaks in the mass spectrum.
 m/z 15.
 m/z 29.
 m/z 43.
v. Use your answer to part (iv) to identify which of the isomers in part (iii) is compound A.
Explain your reasoning. [1]
10. Compound G was extracted from the leaves of a plant. A sample of G was analysed by a research
chemist. A summary of the chemist’s results is shown in the table.

Use this information to suggest a possible structure for compound G.

In your answer, you should make clear how your explanation is linked to the evidence. [8]

11. Mass spectrometry and infrared spectroscopy are used in analysis.

a. The mass spectrum of compound Z is shown below.

Compound Z has the molecular formula C3H6Ox.

i. Using the mass spectrum, deduce the value of x in C C3H6Ox. [2]
ii. Suggest a possible structure for Z. [1]
iii. Suggest the formula of an ion that gives rise to the peak at m/z = 29 in this spectrum. [1]
b. A space probe has detected the presence of the element iron on the surface of the planet Mars.
Outline how a mass spectrum would show the presence of iron. [1]
c. The space probe also detected different isotopes of sulfur on Mars.
i. Outline how the mass spectrum would show how many different isotopes of sulfur were present
on Mars. [1]
ii. The relative atomic mass of the sulfur found by the space probe was different from the relative
atomic mass of sulfur on Earth.
Suggest why. [1]

d. An environmental chemist used infrared spectroscopy to monitor air pollution outside a petrol
station. The infrared spectrum below was obtained from one of these pollutants.
 What evidence is there in the spectrum that the pollutant may be a hydrocarbon rather than an
alcohol or a carbonyl compound? [1]
e. The infrared spectrum of a drug is shown below.

Suggest, with reasons, possible functional group(s) present in the drug. [2]
Analysis Questions Part 3: Optional question – This will require research of esters.

12. Compound X and compound Y react together to make an ester Z. Samples of X and Y were analysed by
a research chemist. A summary of the chemist’s results are shown below.

Use this information to suggest the identity of compound X, compound Y and ester Z.
In your answer you should make clear how your explanation is linked to the evidence. [10]