Alcohols

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Edexcel Chemistry A-level - 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)

(iv) Name this type of stereoisomerism.


(1)
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(Total for question = 6 marks)
Edexcel Chemistry A-level - Alcohols

Q2.

This question is about alcohols and their reactions.

(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

(Total for question = 4 marks)


Edexcel Chemistry A-level - Alcohols

Q3.

Some alcohols can be oxidised by acidified sodium dichromate(VI), Na2Cr2O7.

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)

(Total for question = 2 marks)


Edexcel Chemistry A-level - Alcohols

Q4.

This question is about the chemistry of propane-1,3-diol and propanedioic acid.

In an experiment, 15.2 g of propane-1,3-diol was oxidised to propanedioic acid, which is a


solid dibasic acid. This acid may be represented as H2X.

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.

H2X + 2NaOH → Na2X + 2H2O

[Relative formula masses: propane-1,3-diol = 76.0; propanedioic acid = 104.0]

(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.

Analysis shows that a compound has the molecular formula C4H8O2.

A student suggests that the compound could be either A or B.

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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(Total for question = 2 marks)


Edexcel Chemistry A-level - Alcohols

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 .

This question is about some reactions of cyclohexanol.

(i) Cyclohexanol can be converted to cyclohexene.


What is the classification for this reaction?
(1)
A addition
B elimination
C oxidation
D substitution

(ii) In an experiment, 10.0 cm3 of cyclohexanol was converted to cyclohexene with a 63.0 %
yield.

Calculate the volume of cyclohexene produced.


(4)
Edexcel Chemistry A-level - Alcohols

*(iii) Cyclohexene can be prepared by reacting cyclohexanol with phosphoric(V) acid.


The mixture is warmed in a water bath for 15 minutes before distilling off a mixture of
cyclohexene and water.
Devise a procedure to obtain a pure, dry sample of cyclohexene from the distillate.
Include a reason for each step.
[Boiling temperature of cyclohexene = 83 °C
Density of cyclohexene = 0.811 g cm–3]
(6)

(Total for question = 11 marks)


Edexcel Chemistry A-level - Alcohols

Q7.

This question is about some reactions of cyclohexanol.

(i) Give the name and displayed formula of compound B.


(2)
Edexcel Chemistry A-level - Alcohols

(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

(iii) The mass spectrum of compound B is shown.

Deduce the relative molecular mass of compound B using the mass spectrum. Justify
your answer.
(1)
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(iv) In the mass spectrum of cyclohexanol, there is a peak at m/z = 83.


Give the formula of a fragment that could be responsible for this peak.
(2)

(Total for question = 7 marks)


Edexcel Chemistry A-level - Alcohols

Q8.

Some alcohols can be oxidised by acidified sodium dichromate(VI), Na2Cr2O7.

Reflux apparatus can be used to carry out the oxidation of alcohols.

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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(Total for question = 2 marks)


Edexcel Chemistry A-level - Alcohols

Q9.

The preparation of 2-chloro-2-methylpropane, (CH3)3CCl, involves the reaction of


concentrated hydrochloric acid with 2-methylpropan-2-ol, (CH3)3COH, a tertiary alcohol.

(CH3)3COH + HCl → (CH3)3CCl + H2O

In an experiment, 12.0 g of 2-methylpropan-2-ol was shaken with excess concentrated


hydrochloric acid in a separating funnel.

After about 15 minutes, the product formed as a separate layer.

Data:

Draw a diagram of the separating funnel after 15 minutes, labelling the layer containing
2-chloro-2-methylpropane.
(2)

(Total for question = 2 marks)


Edexcel Chemistry A-level - Alcohols

Q10.

The preparation of 2-chloro-2-methylpropane, (CH3)3CCl, involves the reaction of


concentrated hydrochloric acid with 2-methylpropan-2-ol, (CH3)3COH, a tertiary alcohol.

(CH3)3COH + HCl → (CH3)3CCl + H2O

In an experiment, 12.0 g of 2-methylpropan-2-ol was shaken with excess concentrated


hydrochloric acid in a separating funnel.

After about 15 minutes, the product formed as a separate layer.

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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(Total for question = 4 marks)


Edexcel Chemistry A-level - Alcohols

Q11.

The preparation of 2-chloro-2-methylpropane, (CH3)3CCl, involves the reaction of


concentrated hydrochloric acid with 2-methylpropan-2-ol, (CH3)3COH, a tertiary alcohol.

(CH3)3COH + HCl → (CH3)3CCl + H2O

In an experiment, 12.0 g of 2-methylpropan-2-ol was shaken with excess concentrated


hydrochloric acid in a separating funnel.

After about 15 minutes, the product formed as a separate layer.

Data:

The dried 2-chloro-2-methylpropane was transferred to the distillation apparatus.

(i) State the appropriate temperature range over which to collect the product.
(1)
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* (ii) A diagram of the distillation apparatus is shown.


Edexcel Chemistry A-level - Alcohols

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.

This question is about 2-methylpropan-2-ol.

(a) Draw the fully displayed formula of 2-methylpropan-2-ol.


(1)

(b) The mass spectrum of 2-methylpropan-2-ol is shown.

(i) The relative molecular mass of 2-methylpropan-2-ol is 74.


Give a possible reason why there is no molecular ion peak in the mass spectrum of
2-methylpropan-2-ol.
(1)
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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)

(c) The equation for the complete combustion of 2-methylpropan-2-ol is

(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)

(ii) 2-methylpropan-2-ol burns in air with a smoky flame.


Explain how burning with a smoky flame affects the value of the experimentally
determined enthalpy change of combustion.
(2)
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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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(Total for question = 10 marks)


Edexcel Chemistry A-level - Alcohols

Q13.

This question is about some reactions of cyclohexanol.

Write the skeletal formula of compound A.


(1)

(Total for question = 1 mark)


Edexcel Chemistry A-level - Alcohols

Q14.

This question is about the identification of an alcohol, X.

(a) Alcohol X has the following percentage composition by mass:

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)

(b) (i) When alcohol X is oxidised, a carboxylic acid is formed.


State what information this gives about alcohol X.
(1)
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(ii) Draw the displayed formulae of the four possible structural isomers that could be
alcohol X.
(3)
Edexcel Chemistry A-level - Alcohols

(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)

(iv) Alcohol X has a branched chain.


Identify alcohol X, explaining your reasoning.
(2)

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(Total for question = 9 marks)


Edexcel Chemistry A-level - Alcohols

Q15.

The compound flavan-3-ol is found in tea, fruit and wine.

*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.

This question is about the preparation of a sample of the ketone, 3-methylbutan-2-one.

A student's research suggested that 3-methylbutan-2-one may be prepared by oxidising


3-methylbutan-2-ol with acidified potassium dichromate(VI) solution.

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.

The sample of purified 3-methylbutan-2-one is found to have a mass of 2.15 g.


This mass of 3-methylbutan-2-one represents a yield of 62.5% by mass.

(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)

(Total for question = 4 marks)


Edexcel Chemistry A-level - Alcohols

Q17.

The following procedure may be used to prepare 2-chloro-2-methylpropane.

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

(d) A student set up this apparatus for distillation in Step 7 as shown.

(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

(e) In the preparation, 15cm3 of 2-methylpropan-2-ol produced 6.9 cm3 of


2-chloro-2-methylpropane.
The equation for the reaction is
(CH3)3COH + HCl → (CH3)3CCl + H2O
Calculate the percentage yield of 2-chloro-2-methylpropane, using data from the table.

(3)

(f) The mechanism for the reaction is in three stages.

Add curly arrows to the reactants in Stages 2 and 3 to complete the mechanism.
(2)

(Total for question = 14 marks)


Edexcel Chemistry A-level - Alcohols

Q18.

1-bromobutane can be prepared from butan-1-ol and hydrogen bromide.

CH3CH2CH2CH2OH + HBr → CH3CH2CH2CH2Br + H2O

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.

Identify the three errors, including the effect of each error.


(3)
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Edexcel Chemistry A-level - Alcohols

(iii) The student corrected the errors.


While the mixture was heating under reflux, the student noticed a small
amount of a brown vapour was formed.
Explain why the brown vapour forms.
(2)
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(b) The distillate collected in Step 5 is a mixture consisting of two layers.


There is an aqueous layer and a layer containing impure 1-bromobutane.

The steps for the purification of the 1-bromobutane are summarised.


Step 6 Transfer the mixture from Step 5 to a separating funnel and remove the aqueous
layer.
Step 7 Wash the impure 1-bromobutane with concentrated hydrochloric acid in the
separating funnel.
Remove the aqueous layer.
Step 8 Add aqueous sodium hydrogencarbonate to the impure 1-bromobutane in the
separating funnel.
Step 9 Shake the mixture in the separating funnel and, from time to time, invert the funnel
and open the tap.
Step 10 Collect the 1-bromobutane layer from Step 9 in a small conical flask.
Add anhydrous sodium sulfate and swirl the flask until the liquid becomes clear.
Step 11 Decant the 1-bromobutane into a clean pear-shaped flask and redistil it.
Measure the volume of 1-bromobutane produced.

(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)

(Total for question = 15 marks)


Edexcel Chemistry A-level - Alcohols

Q19.

The preparation of 2-chloro-2-methylpropane, (CH3)3CCl, involves the reaction of


concentrated hydrochloric acid with 2-methylpropan-2-ol, (CH3)3COH, a tertiary alcohol.

(CH3)3COH + HCl → (CH3)3CCl + H2O

Primary alcohols react very slowly with concentrated hydrochloric acid.


State a different reagent for the chlorination of primary alcohols.
(1)
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(Total for question = 1 mark)


Edexcel Chemistry A-level - Alcohols

Q20.

Some alcohols can be oxidised by acidified sodium dichromate(VI), Na2Cr2O7.

Reflux apparatus can be used to carry out the oxidation of alcohols.

(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)

(ii) State how the granules prevent bumping.


(1)
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(Total for question = 2 marks)


Edexcel Chemistry A-level - Alcohols

Q21.

This question is about esters with the molecular formula C6H12O2.

Another ester, A, with molecular formula C6H12O2, was hydrolysed.


It produced ethanoic acid, and an alcohol, B, with molecular formula C4H10O.

Alcohol B undergoes an elimination reaction to produce a mixture of


but-1-ene and but-2-ene.

Deduce the structures of B and A. Justify your structure of B.


(3)

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(Total for question = 3 marks)


Edexcel Chemistry A-level - Alcohols

Q22.

Propanal can be produced from the oxidation of propan-1-ol.

(i) A student assembled the apparatus shown for this oxidation.

Explain why the use of this apparatus would give a very low yield of propanal.
(2)
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(ii) The oxidising agent is acidified Na2Cr2O7.


State the oxidation number of chromium in Na2Cr2O7.
(1)
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(iii) Complete the ionic half-equation for the oxidation of propan-1-ol.


(1)

CH3CH2CH2OH → CH3CH2CHO + ...............H+ + ...............e–

(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)

(Total for question = 8 marks)


Edexcel Chemistry A-level - Alcohols

Q23.

Ethanedioic acid has two carboxylic acid groups.

(a) Ethanedioic acid, H2C2O4, can be prepared from ethane-1,2-diol.

Give the reagents and condition required for this reaction.


(2)
Reagents

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Condition

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(b) The formula for ethanedioic acid crystals is H2C2O4.nH2O.


To determine the number of moles of water of crystallisation, n, in 1 mol of ethanedioic
acid crystals, a student carried out the following procedure.

 Prepare 250.0cm3 of a solution containing a known mass of about 1g of ethanedioic


acid crystals.
 Titrate 25.0cm3 portions of the ethanedioic acid solution with 0.103 mol dm−3 sodium
hydroxide solution, using phenolphthalein as indicator.
The student obtained these results:
mass of ethanedioic acid crystals = 1.09g
mean titre = 16.20cm3
The equation for the reaction is
H2C2O4 + 2NaOH → Na2C2O4 + 2H2O

(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

(ii) Give the colour change at the end-point in this titration.


(1)
From ........................................ to ........................................
(iii) Calculate a value of n in the formula H2C2O4.nH2O from these data.
(5)

(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 is an ester.

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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(Total for question = 3 marks)


Edexcel Chemistry A-level - Alcohols

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.

Deduce the name of the alcohol that forms isoamyl acetate.


(1)
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(Total for question = 1 mark)


Edexcel Chemistry A-level - Alcohols

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)

(Total for question = 5 marks)


Edexcel Chemistry A-level - Alcohols

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.

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