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Questions 1-3 : N/A
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Question 21: N/A
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*N36506A0424*

3 In which reaction is water acting as a Brønsted-Lowry acid?

A H2O + HCl → H3O+ + Cl–

B H2O + SO3 → H2SO4

C H2O + NH3 → NH4+ + OH–

D H2O + CO2 → H2CO3

(Total for Question 3 = 1 mark)

25 Which of the following compounds has both optical and E-Z isomers?

A CH3CH=CHCH2CH3

B CH3CHClCH=C(CH3)2

C CH3CCl=CClCH3

D CH3CHBrCH=CHCl

(Total for Question = 1 mark)

26 Which of the following reacts with hydrogen cyanide, HCN, to make a racemic mixture?

A Methanal, HCHO

B Ethanal, CH3CHO

C Propanone, CH3COCH3

D Pentan-3-one, C2H5COC2H5

(Total for Question = 1 mark)

27 Which of the following is a redox reaction?

A Ethanal reacting with Tollens’ reagent.

B Ethanoyl chloride reacting with ammonia.

C Ethanoic acid reacting with ethanol.

D Ethanoic acid reacting with sodium hydroxide.

(Total for Question = 1 mark)

Use this space for any rough working. Anything you write in this space will gain no credit.

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*N36506A0524* Turn over

28 The following methods can be used to distinguish between pairs of organic compounds without further tests.

A Warm each compound with Fehling’s or Benedict’s solution.

B Add solid sodium carbonate to each compound.

C Add 2,4-dinitrophenylhydrazine (Brady’s reagent) to each compound.

D Add water, drop by drop, to each compound.

(a) Which test would distinguish propanone from propan-1-ol?(1)

A

B

C

D

(b) Which test would distinguish between aqueous solutions of ethanoic acid and ethanol?(1)

A

B

C

D

(c) Which test would distinguish ethanoyl chloride from ethanol?(1)

A

B

C

D

(Total for Question = 3 marks)

Use this space for any rough working. Anything you write in this space will gain no credit.

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*N36506A0624*

29 When propanone reacts with iodine in the presence of sodium hydroxide, the crystalline solid product has the formula

A CH3I

B CHI3

C CH3COCH2I

D CH3COCI3

(Total for Question = 1 mark)

30 When the following reaction mixtures are warmed, which will contain ethanoic acid as one of the products?

A Ethyl methanoate and sodium hydroxide solution.

B Ethyl methanoate and dilute sulfuric acid.

C Methyl ethanoate and sodium hydroxide solution.

D Methyl ethanoate and dilute sulfuric acid.(Total for Question = 1 mark)

31 The spectra of the compounds with the formulae CH3CH(OH)CH3 and CH3CH2CH2OH can be distinguished by

A the value of m/e of the molecular ion in the mass spectrum.

B the presence of a fragment with m/e =15 in the mass spectrum.

C the presence of an absorption peak due to O–H in the infrared spectrum.

D the number of peaks in the nmr spectrum.

(Total for Question = 1 mark)

32 Which of the following has two singlet peaks in its nmr spectrum?

A Methanal, HCHO

B Methanol, CH3OH

C Chloromethane, CH3Cl

D Dichloromethane, CH2Cl2

(Total for Question = 1 mark)

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*N36506A0724* Turn over

33 The nmr spectrum of 2,2-dimethylpropane, H3C—C—CH3, contains

A one singlet peak.

B four singlet peaks.

C one quartet peak.

D four quartet peaks.

(Total for Question = 1 mark)

13 Which of the following solutions has the lowest pH?

A 0.010 mol dm–3 hydrochloric acid.

B 0.100 mol dm–3 hydrochloric acid.

C 0.010 mol dm–3 ethanoic acid.

D 0.100 mol dm–3 ethanoic acid.(Total for Question 13 = 1 mark)

14 Which of the following solutions, when mixed, would make a buffer with pHmore than 7?

A Methanoic acid and sodium methanoate.

B Sodium hydroxide and sodium chloride.

C Ammonia and ammonium chloride.

D Ammonium chloride and ammonium ethanoate.

(Total for Question 14 = 1 mark)

Use this space for any rough working. Anything you write in this space will gain no credit.

CH3

CH3

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*N36506A01224*

34 This question is about butanoic acid, CH3CH2CH2COOH.

(a) Some reactions involving butanoic acid are shown below.

(i) What type of reaction is Reaction A?(1)

. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .

(ii) Identify, by name or formula, the reagent which is used with sulfuric acid to carry out Reaction B.

(1)

. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .

(iii) What reagent is used in Reaction C?(1)

. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .

(iv) Name the organic product of Reaction D and write a balanced equation for its formation.

(2)

Name . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .

Equation

(v) Write the displayed formula for Z, the organic product of the reaction of butanoic acid with phosphorus(V) chloride, PCl5.

(1)

CH3CH2CH2CH2OHCH3CH2CH2CN

CH3CH2CH2COOH

CH3CH2CH2COOCH3

Reaction AReaction B

Reaction C

Reaction DPCl5

Z

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*N36506A01324* Turn over

(b) Butanoic acid and propane-1,2,3-triol are formed when fats in milk are hydrolysed. The presence of milk fat in low fat spreads is detected by hydrolysing the spread, and then analysing the products using gas chromatography (also called gas-liquid chromatography, GLC).

(i) Explain why nitrogen, rather than oxygen, is used as the carrier gas in GLC.(1)

. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .

. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .

(ii) What property determines whether butanoic acid or propane-1,2,3-triol would move faster through the chromatography column?

(1)

. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .

(c) The formula of 3-hydroxybutanoic acid is shown below.

HO—C—CH2—COOH

(i) 3-hydroxybutanoic acid can form a polymer which is used to make “green” packaging as it is biodegradable.

Draw a section of this polymer, showing TWO monomer units. Clearly show any double bonds.

(2)

(ii) The polymer cannot be used in acidic conditions. What reaction would occur when the polymer is in prolonged contact with an acid?

(1)

. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .

. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .

(Total for Question = 11 marks)

H

CH3

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