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3.2.10 Alcohols
Classification of reactions
244 minutes
240 marks
Page 1 of 36
Q1. (a) An alcohol containing carbon, hydrogen and oxygen only has 64.9% carbon and 13.5% hydrogen by mass. Using these data, show that the empirical formula of the alcohol is C
4H
10O
......................................................................................................................
......................................................................................................................
......................................................................................................................
...................................................................................................................... (3)
(b) The structural formulae of two of the four possible alcohols of molecular formula C4H
10O
are shown below.
(i) What type of alcohol is Isomer 1? Suggest a reason why this type of alcohol is not easily oxidised.
Type of alcohol ...................................................................................
Reason ...............................................................................................
(ii) Draw the structural formulae of the two remaining alcohols of molecular formula C
4H
10O
Isomer 3 Isomer 4 (4)
(c) Isomer 2 was oxidised by adding it dropwise to acidified potassium dichromate(VI) solution and immediately distilling off the product. When this product was treated with Fehling’s solution, a red precipitate was formed.
(i) State the type of product distilled off during the oxidation by acidified potassium dichromate(VI) solution.
.............................................................................................................
(ii) Write an equation for the oxidation by potassium dichromate(VI), showing clearly the structure of the organic product. Use [O] to represent the oxidising agent.
.............................................................................................................
Page 2 of 36
(iii) Name and draw a structure for the organic product formed by the reaction with Fehling’s solution.
Name ..................................................................................................
Structure ............................................................................................. (5)
(d) State one advantage and one disadvantage of the production of ethanol by the hydration of ethene compared to the fermentation of glucose.
Advantage ...................................................................................................
Disadvantage ............................................................................................... (2)
(e) Outline a mechanism for the dehydration of ethanol to form ethene in the presence of an acid catalyst.
(4)
(Total 18 marks)
Q2. (a) Ethanol can be manufactured by the direct hydration of ethene and by the fermentation of sugars.
(i) State what is meant by the term hydration.
.............................................................................................................
(ii) Give one advantage and one disadvantage of manufacturing ethanol by fermentation rather than by hydration.
Do not include energy consumption or cost.
Advantage ...........................................................................................
.............................................................................................................
Disadvantage ......................................................................................
............................................................................................................. (3)
Page 3 of 36
(b) Ethanol can be oxidised to an aldehyde and to a carboxylic acid.
(i) Draw the structure of this aldehyde and of this carboxylic acid.
Structure of aldehyde Structure of carboxylic acid
(ii) Give a suitable reagent and reaction conditions for the oxidation of ethanol to form the carboxylic acid as the major product.
Reagent ..............................................................................................
Conditions ...........................................................................................
............................................................................................................. (5)
(c) (i) Draw the structure of an alcohol containing four carbon atoms which is resistant to oxidation.
Page 4 of 36
(ii) Draw the structure of an alcohol containing four carbon atoms which can be oxidised to a ketone.
(2)
(d) In the presence of a catalyst, ethanol can be dehydrated to ethene.
(i) Give a suitable catalyst for use in this reaction.
.............................................................................................................
(ii) Complete the mechanism for this dehydration reaction.
(5)
(Total 15 marks)
Q3. (a) One of the isomers in part (a) is resistant to oxidation by acidified potassium dichromate(VI).
(i) Identify this isomer.
.............................................................................................................
(ii) This isomer can be dehydrated. Give a suitable dehydrating agent and write an equation for this dehydration reaction.
Dehydrating agent................................................................................
Equation .............................................................................................. (3)
Page 5 of 36
(b) (i) Identify the isomer in part (a) which can be oxidised to a ketone. Give the structure of the ketone formed.
Isomer .................................................................................................
Structure of the ketone
(ii) Identify one of the isomers in part (a) which can be oxidised to an aldehyde. Give the structure of the aldehyde formed.
Isomer .................................................................................................
Structure of the aldehyde
(iii) Give a reagent that can be used in a test to distinguish between a ketone and an aldehyde. State what you would observe in the test.
Reagent ..............................................................................................
Observation with ketone ......................................................................
.............................................................................................................
Observation with aldehyde ..................................................................
............................................................................................................. (7)
(c) Butan-1-ol can be oxidised to form a carboxylic acid. Using [O] to represent the oxidising agent, write an equation for this reaction and name the product.
Equation ......................................................................................................
Name of product .......................................................................................... (2)
(Total 12 marks)
Q4. (a) (i) Give a suitable reagent and state the necessary conditions for the conversion of propan-2-ol into propanone. Name the type of reaction.
Reagent ..............................................................................................
Conditions ...........................................................................................
Type of reaction ...................................................................................
Page 6 of 36
(ii) Propanone can be converted back into propan-2-ol. Give a suitable reagent and write an equation for this reaction. (Use [H] to represent the reagent in your equation.)
Reagent ...............................................................................................
Equation
............................................................................................................. (5)
(b) Propanal is an isomer of propanone.
(i) Draw the structure of propanal.
(ii) A chemical test can be used to distinguish between separate samples of propanone and propanal. Give a suitable reagent for the test and describe what you would observe with propanone and with propanal.
Test reagent .........................................................................................
Observation with propanone ................................................................
Observation with propanone ................................................................ (4)
(Total 9 marks)
Page 7 of 36
Q5. Consider the following reaction schemes involving two alcohols, A and B, which are position isomers of each other.
CH3CH
2CH
2CH
2OH → CH
3CH
2CH
2CHO → CH
3CH
2CH
2COOH
A butanal butanoic acid
CH3CH
2CH(OH)CH
3 → CH
3CH
2COCH
3
B C
(a) State what is meant by the term position isomers.
......................................................................................................................
......................................................................................................................
...................................................................................................................... (2)
(b) Name compound A and compound C.
Compound A ...............................................................................................
Compound C ................................................................................................ (2)
(c) Each of the reactions shown in the schemes above is of the same type and uses the same combination of reagents.
(i) State the type of reaction.
.............................................................................................................
(ii) Identify a suitable combination of reagents.
.............................................................................................................
(iii) State how you would ensure that compound A is converted into butanoic acid rather than into butanal.
.............................................................................................................
.............................................................................................................
(iv) Draw the structure of an isomer of compound A which does not react with this combination of reagents.
Page 8 of 36
(v) Draw the structure of the carboxylic acid formed by the reaction of methanol with this combination of reagents.
(6)
(d) (i) State a reagent which could be used to distinguish between butanal and compound C.
.............................................................................................................
(ii) Draw the structure of another aldehyde which is an isomer of butanal.
(2)
(Total 12 marks)
Q6. Some alcohols can be oxidised to form aldehydes, which can then be oxidised further to form carboxylic acids. Some alcohols can be oxidised to form ketones, which resist further oxidation. Other alcohols are resistant to oxidation.
(a) Draw the structures of the two straight-chain isomeric alcohols with molecular formula, C
4H
10O
(2)
(b) Draw the structures of the oxidation products obtained when the two alcohols from part (a) are oxidised separately by acidified potassium dichromate(VI). Write equations for any reactions which occur, using [O] to represent the oxidising agent.
(6)
(c) Draw the structure and give the name of the alcohol with molecular formula C4H
10O which
is resistant to oxidation by acidified potassium dichromate(VI). (2)
(Total 10 marks)
Page 9 of 36
Q7. Glucose, C6H
12O
6, can be converted into ethanol. Ethanol can be used as a fuel or can be
converted into ethene by acid-catalysed dehydration. Most of the ethene used by industry is formed by the thermal cracking of alkanes.
(a) State four essential conditions for the conversion of glucose into ethanol. Name the process and give an equation for the reaction which takes place. Write an equation for the complete combustion of ethanol.
(7)
(b) Explain what is meant by the term dehydration. Identify a catalyst which could be used in the acid-catalysed dehydration of ethanol. Write an equation for the reaction which takes place.
(3)
(c) State what is meant by the term cracking. Describe what happens during the thermal cracking of alkanes and name the type of reactive intermediate. Give an essential condition for this process. Write an equation for the thermal cracking of butane to give ethene as one of the products.
(5) (Total 15 marks)
Q8. Consider the following reaction scheme, which leads to the formation of two compounds V and W.
(a) Give a suitable catalyst for Reaction 1 and name compound V.
Catalyst .......................................................................................................
Name of compound V .................................................................................. (2)
Page 10 of 36
(b) Name and outline a mechanism for Reaction 2.
Name of mechanism ....................................................................................
Mechanism
(5)
(c) In Reaction 4, compound W is distilled from the reaction mixture.
(i) Name compound W and draw its structure.
Name ..................................................................................................
Structure
(ii) Name the type of reaction shown by Reaction 4.
............................................................................................................. (3)
(Total 10 marks)
Page 11 of 36
Q9. There are seven isomeric carbonyl compounds with the molecular formula C5H
10O.
The structures and names of some of these isomers are given below.
(a) (i) Complete the table.
Structure Name
pentanal
2-methybutanal
2, 2-dimethypropanal
pentan-2-one
(ii) Two other isomeric carbonyl compounds with the molecular formula C5H
10O are not
shown in the table. One is an aldehyde and one is a ketone. Draw the structure of each.
isomeric aldehyde isomeric ketone
(4)
(b) Pentanal, CH3CH
2CH
2CH
2CHO, can be oxidised to a carboxylic acid.
(i) Write an equation for this reaction. Use [O] to represent the oxidising agent.
.............................................................................................................
Page 12 of 36
(ii) Name the carboxylic acid formed in this reaction.
............................................................................................................. (2)
(c) Pentanal can be formed by the oxidation of an alcohol.
(i) Identify this alcohol.
.............................................................................................................
(ii) State the class to which this alcohol belongs.
............................................................................................................. (2)
(Total 8 marks)
Q10. (a) In industry, ethanol is made from ethene in an acid-catalysed reaction. Name the type of reaction. Write an equation and identify a suitable catalyst for this reaction.
Type of reaction...........................................................................................
Equation.......................................................................................................
Catalyst ........................................................................................................ (3)
(b) Ethanol burns completely in a plentiful supply of air, but incomplete combustion occurs if the air supply is limited.
(i) Identify a solid pollutant produced by burning ethanol in a limited supply of air.
.............................................................................................................
(ii) Write an equation for the incomplete combustion of ethanol to produce the solid pollutant that you have identified in part (b)(i).
............................................................................................................. (2)
(Total 5 marks)
Q11. (a) Alcohols can be classed as primary, secondary or tertiary. Draw possible structures for a primary, a secondary and a tertiary alcohol which have the molecular formula C
4H
8O.
Which of the structures you have drawn cannot be oxidised by potassium dichromate in acid solution?
(4)
(b) Explain what is meant by the fingerprint region of an infra-red spectrum. State how it is used to confirm the identity of organic molecules such as the primary, secondary and tertiary alcohols of molecular formula C
4H
8O.
(2)
Page 13 of 36
(c) Each of the parts below concerns a different pair of isomers. Deduce one possible structural formula for each of the species A to F. Use, where appropriate, the table of infra-red absorption data given on the data sheet.
(i) A and B have the molecular formula C3H
8O. A has a broad absorption band at
3300 cm–1 in its infra-red spectrum, but B does not.
(ii) C and D have the molecular formula C5H
10. C has a weak absorption band at
1650 cm–1 in its infra-red spectrum, but D does not.
(iii) E and F have the molecular formula C3H
6O and both have strong absorption bands
at about 1700 cm–1 in their infra-red spectra. E reacts with Tollens’ reagent but F does not.
(6) (Total 12 marks)
Q12. There are four isomeric alcohols with the molecular formula C4H
10O
(a) Two of these are butan-l-ol (CH3CH
2CH
2CH
2OH) and butan-2-ol.
The other two isomers are alcohol X and alcohol Y.
Draw the displayed formula for butan-2-ol.
Alcohol X does not react with acidified potassium dichromate(VI) solution. Give the structure of alcohol X.
Name the fourth isomer, alcohol Y.
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...................................................................................................................... (3)
Page 14 of 36
(b) The infrared spectrum of one of these isomeric alcohols is given below.
Identify one feature of the infrared spectrum which supports the fact that this is an alcohol. You may find it helpful to refer to Table 1 on the Data Sheet.
Explain how infrared spectroscopy can be used to identify this isomeric alcohol.
......................................................................................................................
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......................................................................................................................
......................................................................................................................
...................................................................................................................... (3)
(c) British scientists have used bacteria to ferment glucose and produce the biofuel butan-1-ol.
Write an equation for the fermentation of glucose (C6H
12O
6) to form butan-1-ol, carbon
dioxide and water only.
State one condition necessary to ensure the complete combustion of a fuel in air.
Write an equation for the complete combustion of butan-1-ol and state why it can be described as a biofuel.
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......................................................................................................................
...................................................................................................................... (4)
Page 15 of 36
(d) Butan-1-ol reacts with acidified potassium dichromate(VI) solution to produce two organic compounds.
State the class of alcohols to which butan-1-ol belongs.
Draw the displayed formula for both of the organic products.
State the type of reaction that occurs and the change in colour of the potassium dichromate(VI) solution.
......................................................................................................................
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......................................................................................................................
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......................................................................................................................
......................................................................................................................
...................................................................................................................... (5)
(Total 15 marks)
Q13. Consider the following scheme of reactions.
(a) State the type of structural isomerism shown by propanal and propanone.
...................................................................................................................... (1)
(b) A chemical test can be used to distinguish between separate samples of propanal and propanone.
Identify a suitable reagent for the test. State what you would observe with propanal and with propanone.
Test reagent ................................................................................................
Observation with propanal ...........................................................................
Observation with propanone ........................................................................ (3)
Page 16 of 36
(c) State the structural feature of propanal and propanone which can be identified from their infrared spectra by absorptions at approximately 1720 cm–1. You may find it helpful to refer to Table 1 on the Data Sheet.
...................................................................................................................... (1)
(d) The reaction of chlorine with propane is similar to the reaction of chlorine with methane.
(i) Name the type of mechanism in the reaction of chlorine with methane.
............................................................................................................. (1)
(ii) Write an equation for each of the following steps in the mechanism for the reaction of chlorine with propane to form l-chloropropane (CH
3CH
2CH
2Cl).
Initiation step
.............................................................................................................
First propagation step
.............................................................................................................
Second propagation step
.............................................................................................................
A termination step to form a molecule with the empirical formula C3H
7
............................................................................................................. (4)
Page 17 of 36
(e) High resolution mass spectrometry of a sample of propane indicated that it was contaminated with traces of carbon dioxide.
Use the data in the table to show how precise Mr values can be used to prove that the
sample contains both of these gases.
......................................................................................................................
......................................................................................................................
...................................................................................................................... (2)
(Total 12 marks)
Atom Precise relative atomic mass
12C
12.00000
1H
1.00794
16O
15.99491
Q14. Sulfuric acid is an important chemical in many industrial and laboratory reactions. Consider the following three reactions involving sulfuric acid.
Reaction 1 Mg(OH)2 + H
2SO
4 → MgSO
4 + 2H
2O
Reaction 2 The reaction of solid sodium bromide with concentrated sulfuric acid
Reaction 3 H2C=CH
2 + H
2O CH
3CH
2OH
(a) Give a use for magnesium hydroxide in medicine.
...................................................................................................................... (1)
(b) Sulfuric acid behaves as an oxidising agent in Reaction 2.
(i) In terms of electrons, state the meaning of the term oxidising agent.
............................................................................................................. (1)
(ii) Give the formula of the oxidation product that is formed from sodium bromide in Reaction 2.
............................................................................................................. (1)
Page 18 of 36
(iii) Deduce the half-equation for the reduction of H2SO
4 to SO
2 in Reaction 2.
............................................................................................................. (1)
(c) The formation of ethanol in Reaction 3 uses concentrated sulfuric acid and proceeds in two stages according to the following equations.
Stage 1 H2C=CH
2 + H
2SO
4 → CH
3CH
2OSO
2OH
Stage 2 CH3CH
2OSO
2OH + H
2O → CH
3CH
2OH + H
2SO
4
(i) State the overall role of sulfuric acid in Reaction 3.
............................................................................................................. (1)
(ii) Outline a mechanism for Stage 1 of this reaction.
(4)
(iii) State the class of alcohols to which ethanol belongs.
............................................................................................................. (1)
(iv) Draw the displayed formula of the carboxylic acid formed when ethanol is oxidised by an excess of acidified potassium dichromate(VI) solution.
(1)
(Total 11 marks)
Page 19 of 36
Q15. A student devised an experiment to investigate the enthalpies of combustion of some alcohols. The student chose the following series of primary alcohols.
(a) (i) Name alcohol X.
............................................................................................................. (1)
Name Formula
Methanol CH3OH
Ethanol CH3CH
2OH
Propan-1-ol CH3CH
2CH
2OH
Butan-1-ol CH3CH
2CH
2CH
2OH
Pentan-1-ol CH3CH
2CH
2CH
2CH
2OH
Alcohol X CH3CH
2CH
2CH
2CH
2CH
2OH
Heptan-1-ol CH3CH
2CH
2CH
2CH
2CH
2CH
2OH
(ii) State the general name of the type of series shown by these primary alcohols.
............................................................................................................. (1)
(iii) Draw the displayed formula of the position isomer of butan-1-ol.
(1)
(iv) Using [O] to represent the oxidising agent, write an equation for the oxidation of butan-1-ol to form an aldehyde.
............................................................................................................. (1)
(v) Draw the displayed formula of a functional group isomer of this aldehyde.
(1)
Page 20 of 36
(b) The student carried out a laboratory experiment to determine the enthalpy change when a sample of butan-1-ol was burned. The student found that the temperature of 175 g of water increased by 8.0 °C when
5.00 × 10–3 mol of pure butan-1-ol was burned in air and the heat produced was used to warm the water.
Use the student’s results to calculate a value, in kJ mol–1, for the enthalpy change when one mole of butan-1-ol is burned.
(The specific heat capacity of water is 4.18 J K–1 g–1)
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...................................................................................................................... (3)
(c) (i) Give the meaning of the term standard enthalpy of combustion.
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............................................................................................................. (3)
Page 21 of 36
(ii) Use the standard enthalpy of formation data from the table and the equation for the combustion of butan-1-ol to calculate a value for the standard enthalpy of combustion of butan-1-ol.
CH3CH
2CH
2CH
2OH(l) + 6O
2(g) 4CO
2(g) + 5H
2O(l)
.............................................................................................................
.............................................................................................................
.............................................................................................................
.............................................................................................................
.............................................................................................................
............................................................................................................. (3)
CH3CH
2CH
2CH
2OH(l) O
2(g) CO
2(g) H
2O(l)
ΔHf
ο / kJ mol–1 –327 0 –394 –286
Page 22 of 36
(d) The student repeated the experiment described in part (b) and obtained an experimental value for the enthalpy of combustion for each alcohol in this series. These experimental values were then compared with calculated values from standard enthalpies of formation, as shown in the graph below.
(i) In terms of bonds broken and bonds formed, explain why the calculated values of enthalpies of combustion of these alcohols, when plotted against M
r, follow a straight
line.
.............................................................................................................
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.............................................................................................................
............................................................................................................. (2)
(ii) Give two reasons why the experimental values obtained by the student are lower than the calculated values using the enthalpy of formation data.
.............................................................................................................
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.............................................................................................................
............................................................................................................. (2)
(Total 18 marks)
Page 23 of 36
Q16. The following pairs of compounds can be distinguished by observing what happens in test-tube reactions. For each pair, give a suitable aqueous reagent that could be added separately to each compound. Describe what you would observe in each case.
(a) NaF(aq) and NaCl(aq)
Reagent ......................................................................................................
Observation with NaF(aq) ...........................................................................
Observation with NaCl(aq) .......................................................................... (3)
(b) BaCl2(aq) and MgCl
2(aq)
Reagent .......................................................................................................
Observation with BaCl2(aq) ..........................................................................
Observation with MgCl2(aq) ..........................................................................
(3)
(c) AgCl(s) and AgI(s)
Reagent .......................................................................................................
Observation with AgCl(s) .............................................................................
Observation with AgI(s) ............................................................................... (3)
(d) Butan-2-ol(l) and 2-methylpropan-2-ol(l)
Reagent …...................................................................................................
Observation with butan-2-ol(l) .....................................................................
Observation with 2-methylpropan-2-ol(l) ..................................................... (3)
(Total 12 marks)
Page 24 of 36
Q17. The table below shows the structures of three isomers with the molecular formula C5H
10O
(a) Complete the table by naming Isomer 3. (1)
Isomer 1
(E)-pent-3-en-2-ol
Isomer 2
pentanal
Isomer 3
(b) State the type of structural isomerism shown by these three isomers.
..................................................................................................................... (1)
(c) The compound (Z)-pent-3-en-2-ol is a stereoisomer of (E)-pent-3-en-2-ol.
(i) Draw the structure of (Z)-pent-3-en-2-ol.
(1)
(ii) Identify the feature of the double bond in (E)-pent-3-en-2-ol and that in (Z)-pent-3-en-2-ol that causes these two compounds to be stereoisomers.
............................................................................................................. (1)
Page 25 of 36
(d) A chemical test can be used to distinguish between separate samples of Isomer 2 and Isomer 3. Identify a suitable reagent for the test. State what you would observe with Isomer 2 and with Isomer 3.
Test reagent ...............................................................................................
Observation with Isomer 2...........................................................................
.....................................................................................................................
Observation with Isomer 3............................................................................
..................................................................................................................... (3)
(e) The following is the infrared spectrum of one of the isomers 1, 2 or 3.
(i) Deduce which of the isomers (1, 2 or 3) would give this infrared spectrum. You may find it helpful to refer to Table 1 on the Data Sheet.
............................................................................................................. (1)
Page 26 of 36
(ii) Identify two features of the infrared spectrum that support your deduction. In each case, identify the functional group responsible.
Feature 1 and functional group ...........................................................
.............................................................................................................
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.............................................................................................................
Feature 2 and functional group ...........................................................
.............................................................................................................
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............................................................................................................. (2)
(Total 10 marks)
Q18. The table shows the structures and names of three compounds with Mr = 72.0
(a) Explain why Mr values, measured to five decimal places, cannot distinguish between
compounds 1 and 3 but can distinguish between compounds 1 and 2.
........................................................................................................................
........................................................................................................................
........................................................................................................................
........................................................................................................................
........................................................................................................................ (2)
Compound Formula Name
1 CH3CH
2CH
2CHO butanal
2 CH3CH
2CH
2CH
2CH
3
pentane
3 CH3CH
2COCH
3
butanone
Page 27 of 36
(b) A simple chemical test, using either Fehling’s solution or Tollens’ reagent, can be used to distinguish between compound 1 and compound 3. Choose one of these two reagents and state what you would observe with each of compound 1 and compound 3.
Chosen reagent .............................................................................................
Observation with compound 1........................................................................
........................................................................................................................
Observation with compound 3........................................................................
........................................................................................................................ (2)
(Total 4 marks)
Q19. The reaction of butane-1,4-diol with butanedioic acid produces the polymer PBS used in biodegradable packaging and disposable cutlery. Butanedioic acid is produced by two different processes.
Process 1
• Aqueous sodium hydroxide reacts with 1,4-dibromobutane to make butane-1,4-diol.
• Butane-1,4-diol is oxidised to butanedioic acid.
Process 2
• Glucose reacts with carbon dioxide in the presence of microorganisms to produce butanedioic acid directly.
• The carbon dioxide used in this process is obtained from a local factory that produces bioethanol.
(a) Deduce one safety reason and one environmental reason why Process 2 is preferred to Process 1.
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(Extra space) .................................................................................................
........................................................................................................................ (2)
Page 28 of 36
(b) (i) Name and outline a mechanism for the following reaction that occurs in Process 1.
...............................................................................................................
(3)
BrCH2CH
2CH
2CH
2Br + NaOH BrCH
2CH
2CH
2CH
2OH + NaBr
(ii) The infrared spectra shown are those of three compounds.
Compound A 1,4-dibromobutane Compound B butane-1,4-diol Compound C butanedioic acid
Identify the compound responsible for each spectrum by writing the correct letter, A, B or C, in the box next to each spectrum. You may find it helpful to refer to Table 1 on the Data Sheet.
Page 29 of 36
(3)
(c) In the production of bioethanol, glucose (C6H
12O
6) is converted into a dilute aqueous
solution of ethanol and carbon dioxide.
Give the name of this process and state three essential conditions necessary to produce a good yield of ethanol.
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(Extra space) .................................................................................................
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........................................................................................................................ (4)
Page 30 of 36
(d) State the class of alcohols to which the diol butane-1,4-diol belongs.
Identify a suitable reagent or combination of reagents for the conversion of butane-1,4-diol into butanedioic acid (HOOCCH
2CH
2COOH).
Write an equation for this oxidation reaction using [O] to represent the oxidising agent.
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(Extra space) .................................................................................................
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........................................................................................................................ (3)
(Total 15 marks)
Q20. Glucose is an organic molecule. Glucose can exist in different forms in aqueous solution.
(a) In aqueous solution, some glucose molecules have the following structure.
(i) Deduce the empirical formula of glucose.
............................................................................................................... (1)
Page 31 of 36
(ii) Consider the infrared spectrum of solid glucose.
Wavenumber / cm–1
State why it is possible to suggest that in the solid state very few molecules have the structure shown. You may find it helpful to refer to Table 1 on the Data Sheet.
...............................................................................................................
............................................................................................................... (1)
(b) In the absence of oxygen, an aqueous solution of glucose can be fermented to produce ethanol for use in alcoholic drinks.
Write an equation for this fermentation reaction. Give two other essential conditions for the production of ethanol in this fermentation.
Equation
........................................................................................................................
Condition 1 ......................................................................................................
Condition 2 ...................................................................................................... (3)
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(c) Any ethanol present in the breath of a drinker can be detected by using a breathalyser. The ethanol is converted into ethanoic acid. The breathalyser has negative and positive electrodes. A current is measured and displayed in terms of alcohol content.
The overall redox equation is as follows
CH3CH
2OH(I) + O
2(g) CH
3COOH(I) + H
2O(I)
(i) Draw the displayed formula for ethanoic acid.
(1)
(ii) Deduce a half-equation for the reduction of atmospheric oxygen to water in acidic solution at one electrode of the breathalyser.
............................................................................................................... (1)
(iii) Deduce a half-equation for the oxidation of ethanol in water to ethanoic acid at the other electrode of the breathalyser.
............................................................................................................... (1)
(iv) The earliest breathalysers used laboratory chemicals to oxidise the ethanol to ethanoic acid. Detection was by a colour change.
Identify a reagent or combination of reagents that you would use in the laboratory to oxidise ethanol to ethanoic acid. State the colour change that you would expect to see.
Reagent or combination of reagents .......................................................
Colour change ......................................................................................... (2)
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(d) The fermentation of glucose from crops is the main method for the production of ethanol. The product is called bioethanol. The European Union has declared that bioethanol is carbon-neutral.
(i) State the meaning of the term carbon-neutral.
...............................................................................................................
...............................................................................................................
...............................................................................................................
(Extra space) .......................................................................................
............................................................................................................... (1)
(ii) Other than carbon-neutrality, state the main advantage of the use of glucose from crops as the raw material for the production of ethanol.
...............................................................................................................
............................................................................................................... (1)
(iii) Give one disadvantage of the use of crops for the production of ethanol.
...............................................................................................................
............................................................................................................... (1)
(Total 13 marks)
Q21. In each of the following questions, you should draw the structure of the compound in the space provided.
(a) Draw the structure of the alkene that would form 1,2-dibromo-3-methylbutane when reacted with bromine.
(1)
(b) Draw the structure of the alcohol with molecular formula C4H
10O that is resistant to
oxidation by acidified potassium dichromate(VI).
(1)
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(c) Draw the structure of the alkene that has a peak, due to its molecular ion, at m/z = 42 in its mass spectrum.
(1)
(d) Draw the structure of the organic product with Mr = 73, made from the reaction between 2-
bromobutane and ammonia.
(1)
(Total 4 marks)
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