Alcohols
Alcohols
Alcohols
Questions
Q1.
Answer the question with a cross in the box you think is correct . If you change
your mind about an answer, put a line through the box and then mark your new
answer with a cross .
This question is about alcohols and their reactions.
(i) Some alcohols react with concentrated phosphoric acid to form alkenes.
What is the type of this reaction?
(1)
A addition
B elimination
C oxidation
D substitution
(ii) When butan-2-ol reacts with concentrated phosphoric acid, two stereoisomers are
formed.
Explain what is meant by the term stereoisomers.
(2)
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(iii) Draw the structures and give the names of the two stereoisomers.
(2)
Q2.
(i) CH3CH2CH2CH2OH reacts with the oxidising agent potassium dichromate(VI) in dilute
sulfuric acid.
Two organic products can be formed, depending on the conditions.
Write a balanced equation for the formation of one of these products, giving its name and
the condition required to achieve this product in high yield.
Use [O] in the equation to represent each oxygen atom from the oxidising agent.
(3)
Equation
Name
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Condition
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Answer the question with a cross in the box you think is correct . If you change
your mind about an answer, put a line through the box and then mark your new
answer with a cross .
(ii) The colour of the solution at the end of the reaction in (i) will be
(1)
A brown
B green
C orange
D yellow
Q3.
Balance the ionic half-equation for the reduction of the dichromate(VI) ion.
Give the colours of all of the species involved, or state colourless if appropriate.
(2)
Q4.
250 cm3 of a solution was prepared from all of the acid in a volumetric flask.
10.0 cm3 portions of this solution were then titrated with 0.400 mol dm–3 sodium hydroxide
solution. The mean titre was 18.45 cm3.
(i) Calculate the moles of propanedioic acid in 10.0 cm3 of the acid solution.
(2)
(ii) Calculate the mass of propanedioic acid in the 250 cm3 solution.
(2)
(iii) Calculate the percentage yield for the oxidation of propane-1,3-diol to propanedioic acid.
(2)
(iv) Give one reason why the yield calculated in (iii) is less than 100%.
(1)
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(Total for question = 7 marks)
Edexcel Chemistry A-level - Alcohols
Q5.
Deduce a chemical test which would give a positive result for B but not for A.
Include the reagent and observation.
(2)
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Q6.
Answer the question with a cross in the box you think is correct . If you change
your mind about an answer, put a line through the box and then mark your new
answer with a cross .
(ii) In an experiment, 10.0 cm3 of cyclohexanol was converted to cyclohexene with a 63.0 %
yield.
Q7.
(ii) The infrared (IR) spectra of cyclohexanol and compound B are shown.
Identify the bonds, using both IR spectra, that help to confirm the reaction of
cyclohexanol to produce compound B.
Your answer must include the wavenumber ranges of any relevant bonds.
(2)
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Edexcel Chemistry A-level - Alcohols
Deduce the relative molecular mass of compound B using the mass spectrum. Justify
your answer.
(1)
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Q8.
Using the apparatus for distillation instead of reflux is not an efficient way to produce
ethanoic acid from ethanol. Explain why.
(2)
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Q9.
Data:
Draw a diagram of the separating funnel after 15 minutes, labelling the layer containing
2-chloro-2-methylpropane.
(2)
Q10.
Data:
After separation, the organic layer was shaken with sodium hydrogencarbonate solution.
Fizzing was observed.
(i) Identify, by name or formula, the gas that was given off.
(1)
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(ii) Give the formula of the ion that reacted with the hydrogencarbonate ion to form the gas.
(1)
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(iii) Describe how to dry the organic layer to prepare it for distillation.
Include the name of a suitable drying agent.
(2)
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Q11.
Data:
(i) State the appropriate temperature range over which to collect the product.
(1)
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Discuss the improvements that should be made to the set-up of the apparatus. Include the
likely effect of the errors identified on the yield or purity of the product.
Assume the apparatus is suitably clamped.
(6)
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(Total for question = 7 marks)
Edexcel Chemistry A-level - Alcohols
Q12.
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Edexcel Chemistry A-level - Alcohols
(ii) Write the formula for a species that could be responsible for the peak at m / z = 59.
(1)
(i) Using the bond enthalpies shown in the table, calculate a value for the enthalpy
change, in kJ mol−1, for the complete combustion of 2-methylpropan-2-ol.
(4)
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(iii) A Data Book value for the enthalpy change of combustion of 2-methylpropan-2-ol is
−2643.8 kJ mol−1.
Give the main reason for the difference between this value and your answer to part
(c)(i).
(1)
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Q13.
Q14.
The molecular ion peak in the mass spectrum for alcohol X occurs at m/z = 88.
Use all of these data to show that the molecular formula for alcohol X is C5H12O. Include
your working.
(2)
(iii) The mass spectrum of alcohol X has a major peak at m/z = 45.
Draw the structure of the species that could give this peak.
(1)
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Q15.
*A sample of flavan-3-ol extracted from wine contained some ethanol. The sample
was left in a flask, open to the air for several days. The contents were then analysed
to identify any new compounds formed. Several new compounds were found to be
present, including some with a distinctive fruity smell.
Identify four new organic compounds that could form under these conditions
by considering the chemistry of alcohols. Justify your answers. Include the
structure of two compounds formed from flavan-3-ol, one of which has a fruity smell.
(6)
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(Total for question = 6 marks)
Edexcel Chemistry A-level - Alcohols
Q16.
The student sets up the apparatus as shown in the diagram. You may assume that all the
equipment is suitably clamped.
The student adds dilute sulfuric acid to the pear-shaped flask. A mixture of potassium
dichromate(VI) and 3-methylbutan-2-ol is then added slowly to the dilute sulfuric acid in the
flask.
(i) Write an equation, using molecular formulae, for the oxidation of 3-methylbutan-2-ol to
3-methylbutan-2-one.
Use [O] to represent the oxidising agent.
(2)
Edexcel Chemistry A-level - Alcohols
(ii) Calculate the mass of 3-methylbutan-2-ol that the student uses at the start of the
preparation.
(2)
Q17.
Some data on the organic reactant and product are given in the table.
(a) Draw a diagram of a separating funnel, labelling the aqueous layer and the layer of
2-chloro-2-methylpropane that would be observed at the end of Step 2.
(2)
(b) Give the reason why sodium hydrogencarbonate solution is added to the organic layer
in Step 4 and why it is important to open the tap after adding this solution.
(2)
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Edexcel Chemistry A-level - Alcohols
(c) Which one of these anhydrous compounds may be used as a drying agent in Step 6?
(1)
A sodium chloride
B sodium hydroxide
C sodium nitrate
D sodium sulfate
(i) Describe three ways in which this apparatus must be modified for safe and efficient
use. Assume the apparatus is suitably clamped.
(3)
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(ii) Give a suitable temperature range over which to collect the final product during the
distillation.
(1)
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Edexcel Chemistry A-level - Alcohols
(3)
Add curly arrows to the reactants in Stages 2 and 3 to complete the mechanism.
(2)
Q18.
Hydrogen bromide can be made from sodium bromide and 50% concentrated sulfuric acid.
(a) The steps for the preparation of impure 1-bromobutane are summarised.
Step 1 Dissolve the sodium bromide in distilled water in a pear-shaped flask and then
add 20.0 cm3 of butan-1-ol.
Step 2 Surround the flask with an ice bath to cool the mixture, before adding
concentrated sulfuric acid drop by drop.
Step 3 Remove the flask from the ice bath and add a few anti-bumping granules to the
reaction mixture.
Step 4 Set up the apparatus for heating under reflux. Heat the mixture in the flask for 30
minutes and then allow the apparatus to cool.
Step 5 Rearrange the apparatus for distillation and heat the mixture until no more
1-bromobutane distils over.
(i) Parts of the method are given in bold type in Steps 2, 3 and 4.
Give a reason why each of these parts is necessary.
(3)
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Edexcel Chemistry A-level - Alcohols
(ii) A student drew a diagram of the apparatus used for heating under reflux in Step 4.
There are three errors in the apparatus shown in the diagram.
Assume the apparatus is suitably clamped.
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Edexcel Chemistry A-level - Alcohols
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(i) State the position of the aqueous layer in the separating funnel at the start of Step 6.
Justify your answer.
(1)
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Edexcel Chemistry A-level - Alcohols
(ii) Concentrated hydrochloric acid is used to remove any unreacted butan-1-ol in the
mixture in Step 7.
Give the reasons for carrying out Steps 8, 9 and 10.
(3)
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(iii) Give a suitable temperature range over which to collect the pure 1-bromobutane in
the redistillation in Step 11.
(1)
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(iv) The volume of 1-bromobutane collected was 12.0 cm3.
Calculate the number of molecules of 1-bromobutane produced in this experiment.
Give your answer to an appropriate number of significant figures.
(2)
Q19.
Q20.
(i) This Liebig condenser has been set up incorrectly. Add shading to the diagram to show
the water in the condenser, illustrating the effect of the incorrect water flow.
(1)
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Q21.
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Q22.
Explain why the use of this apparatus would give a very low yield of propanal.
(2)
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(iv) State how the use of anti-bumping granules gives smoother boiling.
(1)
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Edexcel Chemistry A-level - Alcohols
(v) Another student used the correct apparatus for this oxidation. 1.50 g of propan-1-ol
produced 0.609 g of propanal.
Calculate the percentage yield of propanal by mass.
(3)
Q23.
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Condition
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(i) Describe how the student should prepare the 250.0 cm3 of ethanedioic acid solution.
(4)
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Edexcel Chemistry A-level - Alcohols
(iv) The student thought that the ethanedioic acid crystals used may have been slightly
damp.
Explain the effect of using damp crystals on the titre and on the value of n.
(2)
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(Total for question = 14 marks)
Edexcel Chemistry A-level - Alcohols
Q24.
Ethyl ethanoate can also be formed by reacting ethanol with ethanoyl chloride, CH3COCl.
Identify three differences in the esterification reaction when ethanoyl chloride is used instead
of ethanoic acid.
(3)
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Q25.
Esters have many uses due to their characteristic aromas and often have common names.
For example, isoamyl acetate is referred to as banana oil and amyl acetate has a scent
similar to apples.
Q26.
Esters have many uses due to their characteristic aromas and often have common names.
For example, isoamyl acetate is referred to as banana oil and amyl acetate has a scent
similar to apples.
The carboxylic acid used to make isoamyl acetate and amyl acetate can also be used to
make six further ester isomers. The structures of two of these esters, A and B, are shown.
(i) Complete the skeletal formulae of three of the remaining esters. Names are not
required.
(3)
(ii) Write an equation to show the formation of ester A from an acyl chloride and an alcohol.
(2)
Mark Scheme
Q1.
Edexcel Chemistry A-level - Alcohols
Q2.
Edexcel Chemistry A-level - Alcohols
Q3.
Q4.
Edexcel Chemistry A-level - Alcohols
Edexcel Chemistry A-level - Alcohols
Q5.
Edexcel Chemistry A-level - Alcohols
Q6.
Edexcel Chemistry A-level - Alcohols
Edexcel Chemistry A-level - Alcohols
Q7.
Edexcel Chemistry A-level - Alcohols
Q8.
Edexcel Chemistry A-level - Alcohols
Q9.
Q10.
Edexcel Chemistry A-level - Alcohols
Q11.
Edexcel Chemistry A-level - Alcohols
Edexcel Chemistry A-level - Alcohols
Edexcel Chemistry A-level - Alcohols
Q12.
Edexcel Chemistry A-level - Alcohols
Edexcel Chemistry A-level - Alcohols
Q13.
Edexcel Chemistry A-level - Alcohols
Q14.
Edexcel Chemistry A-level - Alcohols
Edexcel Chemistry A-level - Alcohols
Edexcel Chemistry A-level - Alcohols
Q15.
Edexcel Chemistry A-level - Alcohols
Q16.
Edexcel Chemistry A-level - Alcohols
Q17.
Edexcel Chemistry A-level - Alcohols
Edexcel Chemistry A-level - Alcohols
Edexcel Chemistry A-level - Alcohols
Q18.
Edexcel Chemistry A-level - Alcohols
Edexcel Chemistry A-level - Alcohols
Edexcel Chemistry A-level - Alcohols
Q19.
Edexcel Chemistry A-level - Alcohols
Q20.
Edexcel Chemistry A-level - Alcohols
Q21.
Edexcel Chemistry A-level - Alcohols
Q22.
Edexcel Chemistry A-level - Alcohols
Edexcel Chemistry A-level - Alcohols
Q23.
Edexcel Chemistry A-level - Alcohols
Edexcel Chemistry A-level - Alcohols
Q24.
Q25.
Edexcel Chemistry A-level - Alcohols
Q26.