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Q1. A (CH3)2CHCH(OH)CH3 undergoes reactions separately with acidified dichromate(VI) and with concentrated .

(a) Deduce the IUPAC name for alcohol A.

______(1)

(b) Draw the structure of the organic product, B, formed when A is oxidised in the reaction with acidified potassium dichromate(VI).

(1)

(c) Two isomeric alkenes, C and D, are formed when A is dehydrated in the reaction with concentrated sulfuric acid.

Name the mechanism for this dehydration reaction.

______(1)

(d) Draw the structure of each isomer.

Isomer C Isomer D

(2)

Alcohols SCT Page 1 of 20 (e) Name the type of structural isomerism shown by C and D.

______(1)

(f) List alcohol A, product B and isomer C in order of increasing boiling point.

______(1)

(g) Draw the structure of the isomer of A that is not oxidised by acidified potassium dichromate(VI).

(1)

(h) Draw the structure of the isomer of A that cannot be dehydrated to form an alkene by reaction with concentrated sulfuric acid.

(1) (Total 9 marks)

Alcohols SCT Page 2 of 20 Q2. (a) Propanoic acid can be made from propan-1-ol by oxidation using acidified potassium dichromate(VI). Propanal is formed as an intermediate during this oxidation.

(i) State the colour of the species after the potassium dichromate(VI) has reacted.

______(1)

(ii) Describe the experimental conditions and the practical method used to ensure that the acid is obtained in a high yield. Draw a diagram of the assembled apparatus you would use.

Conditions ______

______

Apparatus

(4)

(iii) Describe the different experimental conditions necessary to produce propanal in high yield rather than propanoic acid.

______

______(2)

(b) Propan-1-ol is a volatile, flammable liquid. Give one safety precaution that should be used during the reaction to minimise this hazard.

______(1)

Alcohols SCT Page 3 of 20 (c) A student followed the progress of the oxidation of propan-1-ol to propanoic acid by extracting the organic compounds from one sample of reaction mixture.

(i) Give a chemical reagent which would enable the student to confirm the presence of propanal in the extracted compounds. State what you would observe when propanal reacts with this reagent.

Reagent ______

Observation ______

______(2)

(ii) Give a chemical reagent that would enable the student to confirm the presence of propanoic acid in the extracted compounds. State what you would observe when propanoic acid reacts with this reagent.

Reagent ______

Observation ______

______(2)

(d) Predict which one of the compounds, propan-1-ol, propanal and propanoic acid will have the highest boiling point. Explain your answer.

Prediction ______

Explanation ______

______

______

______

______(3) (Total 15 marks)

Alcohols SCT Page 4 of 20 Q3. This question concerns the oxidation of a primary alcohol.

The experiment was carried out using the distillation apparatus shown in the diagram. The oxidation product was distilled off as soon as it was formed.

(a) Suggest the identity of reagent P.

______(1)

(b) State the chemical change that causes the solution in the flask to appear green at the end of the reaction.

______(1)

(c) Give one reason why using a water bath is better than direct heating with a Bunsen burner.

______

______(1)

(d) Suggest a reagent that could be used to confirm the presence of an in the distillate. State the observation you would expect to make if an aldehyde were present.

Reagent ______

Observation ______(2) (Total 5 marks)

Alcohols SCT Page 5 of 20 Q4. There are seven isomeric carbonyl compounds with the molecular formula C5H10O. The structures and names of some of these isomers are given below.

Structure Name

pentanal

2-methybutanal

2, 2-dimethypropanal

pentan-2-one

(a) (i) Complete the table.

(ii) Two other isomeric carbonyl compounds with the molecular formula C5H10O are not shown in the table. One is an aldehyde and one is a . Draw the structure of each.

isomeric aldehyde isomeric ketone

(4)

Alcohols SCT Page 6 of 20 (b) Pentanal, CH3CH2CH2CH2CHO, can be oxidised to a .

(i) Write an equation for this reaction. Use [O] to represent the oxidising agent.

______

(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)

Alcohols SCT Page 7 of 20 Q5. There are four isomeric alcohols with the molecular formula C4H10O

(a) Two of these are butan-l-ol (CH3CH2CH2CH2OH) 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.

______

______

______(3)

(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.

______

______

______

______

______(3)

Alcohols SCT Page 8 of 20 (c) British scientists have used bacteria to ferment glucose and produce the biofuel butan-1-ol.

Write an equation for the fermentation of glucose (C6H12O6) 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.

______

______

______

______

______

______

______

______(4)

(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.

______

______

______

______

______

______

______(5) (Total 15 marks)

Alcohols SCT Page 9 of 20 Q6. Ethanal is prepared by heating with potassium dichromate(VI) in the presence of sulfuric acid. Figures 1 and 2 show two possible ways of heating this reaction mixture.

Figure 1 Figure 2

State which arrangement would not be suitable for the preparation of ethanal. Explain your answer.

Arrangement ______

Explanation ______

______(Total 2 marks)

Alcohols SCT Page 10 of 20 Q7. The table below shows the structures of three isomers with the molecular formula C5H10O

Isomer 1

(E)-pent-3-en-2-ol

Isomer 2

pentanal

Isomer 3

(a) Complete the table by naming Isomer 3. (1)

(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)

Alcohols SCT Page 11 of 20 (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)

(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 ______

______

______

Feature 2 and functional group ______

______

______

______(2) (Total 10 marks)

Alcohols SCT Page 12 of 20 Mark schemes

Q1. (a) 3-methylbutan-2-ol 1

(b)

Allow (CH3)2CHCOCH3 1

(c) Elimination 1

(d)

Allow (CH3)2C=CHCH3 1

Allow (CH3)2CHCH=CH2 1

(e) Position 1

(f) C B A 1

(g)

Allow (CH3)2C(OH)CH2CH3 1

(h)

Alcohols SCT Page 13 of 20

Allow (CH3)3CCH2OH 1 [9]

Q2. (a) (i) Green Ignore shades of green. 1

(ii) Excess acidified potassium dichromate(VI) 1

Reflux (for some time) 1

In the diagram credit should be given for • a vertical condenser Lose M3 and M4 for a distillation apparatus. 1

• an apparatus which would clearly work Do not allow this mark for a flask drawn on its own. Penalise diagrams where the apparatus is sealed. 1

(iii) Distillation 1

Immediately (the reagents are mixed) 1

(b) Keep away from naked flames Allow heat with water-bath or heating mantle. If a list is given ignore eye protection, otherwise lose this mark. 1

(c) (i) Tollens’ or Fehling’s reagents Incorrect reagent(s) loses both marks. Accept mis-spellings if meaning is clear. 1

Silver mirror / red ppt. formed Accept ‘blue to red’ but not ‘red’ alone. 1

(ii) Sodium carbonate (solution) / Group II metal Allow indicator solutions with appropriate colours. Accept any named carbonate or hydrogen carbonate. 1

Alcohols SCT Page 14 of 20 Effervescence / evolves a gas Accept ‘fizzes’. 1

(d) Propanoic acid If this mark is lost allow one mark if there is reference to stronger intermolecular forces in the named compound. Lose M1 and M3. 1

Contains hydrogen bonding 1

Some comparison with other compounds explaining that the intermolecular forces are stronger in propanoic acid 1 [15]

Q3.

(a) H2SO4

Allow H3PO4 or HCl 1

(b) Dichromate / Cr(VI) reduced or Cr(III) formed. Allow Cr6+ and Cr3+ 1

(c) The alcohol is flammable Allow enables temperature to be controlled 1

(d) Tollens’ 1

Silver mirror OR Fehling’s Red precipitate OR Benedict’s Red precipitate 1 [5]

Q4. (a) (i) M1 pentan-3-one only 1

M2 CH3CH2CH2COCH3 (insist on C=O being drawn out)

(penalise use of C3H7) 1

(ii) aldehyde (CH3)2CHCH2CHO 1

ketone (CH3)2CHCOCH3

Alcohols SCT Page 15 of 20 1 (insist on a clear structure for the C=O of the functional groups, but do not be too harsh on the vertical bonds between carbon atom son this occasion) (If both structures correct, but wrong way around, award one mark) (ignore names)

(b) (i) CH3CH2CH2CH2CHO + [O] → CH3CH2CH2CH2COOH

(accept C4H9CHO going to C4H9COOH) (insist on a balanced equation – for example do not credit [O] over the arrow alone) 1

(ii) pentanoic acid (credit pentan–1–oic acid) 1

(c) (i) CH3CH2CH2CH2CH2OH OR pentan–1–ol (If both a structure and a formula are given, credit either correct one of these provided the other is a good, if imperfect, attempt) 1

(ii) Primary (credit 1o or 1) 1 [8]

Q5. (a) M1 Displayed formula for butan-2-ol

M1 displayed formula must have all bonds drawn out, including the O―H but ignore angles Penalise “sticks”

M2 Alcohol X is

M2 structure must be clearly identifiable as 2-methylpropan-2-ol and may be drawn in a variety of ways.

M3 Alcohol Y is named (2)-methylpropan-1-ol ONLY

Alcohols SCT Page 16 of 20 M3 must be correct name, but ignore structures 3

(b) M1 The infrared spectrum shows an absorption/peak in the range 3230 to 3550 (cm–1)(which supports the idea that an alcohol is present) In M1, allow the words “dip”, “spike”, “low transmittance” and “trough” as alternatives for absorption.

M2 Reference to the ‘fingerprint region’ or below 1500 (cm–1)

M3 Match with or same as known sample/database spectra Check the spectrum to see if alcohol OH is labelled and credit.

OR

M2 Run infrared spectra (of the alcohols)

M3 Find which one matches or is the same as this spectrum. 3

(c) M1 balanced equation C6H12O6 → CH3CH2CH2CH2OH + 2CO2 + H2O or C4H9OH Or multiples for M1 and M3 In M1 and M3 penalise use of C4H10O or butan-2-ol once only

M2 Any one from

• excess/adequate/sufficient/correct amount of/enough/plenty/ a good supply of or air

• good mixing of the fuel and air/oxygen For M2, do not accept simply “oxygen” or “air” alone Ignore reference to “temperature”

M3 CH3CH2CH2CH2OH + 6O2 → 4CO2 + 5H2O or C4H9OH

M4 A biofuel is a fuel produced from (renewable) biological (re)source(s)

OR

(renewable) (re)source(s) from (a specified) plant(s)/fruit(s)/tree(s) In M4 Ignore references to “carbon neutral” Ignore “sugar” and “glucose” 4

(d) M1 butan-1-ol is a primary or 1° (alcohol)

M2 Displayed formula (ONLY) for butanal CH3CH2CH2CHO

M3 Displayed formula (ONLY) for butanoic acid CH3CH2CH2COOH M2 and M3 displayed formula must have all bonds drawn out including the O―H but ignore angles.

Alcohols SCT Page 17 of 20 If butanal and butanoic acid formulae are both correctly given but not displayed, credit one mark out of two.

M4 Oxidation (oxidised) OR Redox

M5 orange to green Both colours required for M5 Ignore states 5 [15]

Q6. Figure 2 1

Further oxidation will occur / ethanoic acid formed Do not accept ‘poor yield’ without qualification Can gain this mark if logic correct but has chosen wrong Figure 1 [2]

Q7. (a) Pentan-2-one ONLY but ignore absence of hyphens 1

(b) Functional group (isomerism) Both words needed 1

(c) (i)

Award credit provided it is obvious that the candidate is drawing the Z / cis isomer

The group needs to be CHOHCH3 but do not penalise poor C–C bonds or absence of brackets around OH Trigonal planar structure not essential 1

(ii) Restricted rotation (about the C=C)

OR

No (free) rotation (about the C=C) 1

(d) M1 Tollens’ (reagent) M1 Fehling’s (solution) / Benedict’s

2+ (Credit ammoniacal silver (Penalise Cu (aq) or CuSO4 but

Alcohols SCT Page 18 of 20 OR a description of making mark M2 and M3) Tollens’)

+ (Do not credit Ag , AgNO3 or + [Ag(NH3)2 ] or “the silver mirror test” on their own, but mark M2 and M3)

M2 silver mirror M2 Red solid/precipitate

OR black solid or black precipitate (Credit orange or brown solid)

M3 (stays) colourless M3 (stays) blue

OR OR

no (observed) change / no reaction no (observed) change / no reaction

If M1 is blank CE = 0, for the clip Check the partial reagents listed and if M1 has a totally incorrect reagent, CE = 0 for the clip Allow the following alternatives M1 (acidified) potassium dichromate(VI) (solution); mark on from incomplete formulae or incorrect M2 (turns) green M3 (stays) orange / no (observed) change / no reaction OR M1 (acidified) potassium manganate(VII) (solution); mark on from incomplete formulae or incorrect oxidation state M2 (turns) colourless M3 (stays) purple / no (observed) change / no reaction In all cases for M3 Ignore “nothing (happens)” Ignore “no observation” 3

(e) (i) Spectrum is for Isomer 1

or named or correctly identified The explanation marks in (e)(ii) depend on correctly identifying Isomer 1. The identification should be unambiguous but candidates should not be penalised for an imperfect or incomplete name. They may say “the alcohol” or the “alkene” or the “E isomer” 1

(ii) If Isomer 1 is correctly identified, award any two from

• (Strong / broad) absorption / peak in the range 3230 to 3550 cm–1 or specified value in this range or marked correctly on spectrum

Alcohols SCT Page 19 of 20 and (characteristic absorption / peak for) OH group /alcohol group

• No absorption / peak in range 1680 to 1750 cm–1 or absence marked correctly on spectrum and (No absorption / peak for a) C=O group / carbonyl group / carbon-oxygen double bond

• Absorption / peak in the range 1620 to 1680 cm–1 or specified value in this range or marked correctly on spectrum and

(characteristic absorption / peak for) C=C group / alkene / carbon-carbon double bond If 6(e)(i) is incorrect or blank, CE=0 Allow the words “dip” OR “spike” OR “trough” OR “low transmittance” as alternatives for absorption. Ignore reference to other absorptions e.g. C-H, C-O 2 [10]

Alcohols SCT Page 20 of 20