2019 ife and ealth sciences - ccea

TIME1 hour 45 minutes.

INSTRUCTIONS TO CANDIDATESWrite your Centre Number and Candidate Number in the spaces provided at the top of this page.Answer all six questions.Write your answers in the spaces provided in this question paper.

INFORMATION FOR CANDIDATESThe total mark for this paper is 100.Figures in brackets printed down the right-hand side of pages indicate the marks awarded to each question or part question.Your attention is drawn to the Data leaflet which is used with the question paper.You may use an electronic calculator.Quality of written communication will be assessed in Question 5(a).

12306

For Examiner’suse only

Question Number Marks

1 2 3 4 56

TotalMarks

Centre Number

Candidate Number

Life and Health Sciences

Assessment Unit A2 2assessing

Organic Chemistry

[AZ021]TUESDAY 28 MAY, AFTERNOON

ADVANCEDGeneral Certificate of Education

2019

*AZ021*

AZ0

21

12306 2

Examiner OnlyMarks Remark

1 Alkanes and alkenes react with halogens. Alkenes also react with hydrogen bromide.

(a) Two reactions of ethene are shown below.

CH3CH2OH CH2BrCH2BrCH2 CH2

substance Xbromine water

(i) What colour change is observed when ethene reacts with brominewater?

[2]

(ii) State the IUPAC name of CH2BrCH2Br.

[2]

(iii) Identify substance X.

[1]

(b) The diagram below shows some details of the mechanism for thereaction of ethene with hydrogen bromide.

Reactants Intermediates Product

(i) In the reactants stage, draw two curly arrows to show theformation of the intermediates. [2]

(ii) What general name is given to the positively charged organicintermediate?

[1]

12306 3 [Turn over


(iii) In the intermediates stage, draw a curly arrow to show theformation of the product. [1]

(iv) State the IUPAC name of the product.

[1]

(v) What is the name of this mechanism?

[2]

(vi) Write a balanced symbol equation for the reaction of ethene withhydrogen bromide.

[1]

(c) Alkanes and halogenoalkanes react with halogens. One reactionwhich occurs is shown below.

CH3F + F2 CH2F2 + HF

(i) State the IUPAC name of CH3F and CH2F2.

CH3F

CH2F2 [1]

(ii) What name is given to this type of reaction?

[1]

(iii) Write a balanced symbol equation for the reaction of methanewith fluorine forming tetrafluoromethane.

[2]

12306 4


2 (a) Four different alcohols, all with the same formula C5H11OH, were labelled A, B, C and D.

(i) Complete the table giving the IUPAC name, structural formula andclassification (P = primary, S = secondary, T = tertiary) for eachalcohol.

Alcohol IUPAC name Structural formula Classification

A P

B pentan-2-ol

C P

D

[6]

(ii) Which alcohol(s) (A, B, C, D) can undergo oxidation to form aketone?

[1]

(iii) Draw the structural formula and state the IUPAC name of anotherprimary alcohol, apart from alcohols A and C, which has theformula C5H11OH.

IUPAC name: [2]

12306 5 [Turn over


(b) Alcohol A from the table in (a)(i) reacts as shown below in thepresence of a catalyst.

(i) Name the type of reaction shown above.

[1]

(ii) State the IUPAC name of the organic product of the reaction.

[1]

(iii) Name the catalyst used in this reaction.

[2]

(iv) Alcohol C undergoes the same type of reaction. Complete theequation below for this reaction and state the IUPAC name of theorganic product.

IUPAC name: [2]

12306 6


3 Crude oil is a complex mixture of hydrocarbons.

(a) The diagram below shows how crude oil is processed.

Crude oil

Process A

Process B

Some branched hydrocarbons

Process C

Some unsaturated hydrocarbons

Simpler mixtures of saturated hydrocarbons

(i) Name processes A, B and C.

A

B

C [3]

(ii) What is meant by the term unsaturated?

[1]

(iii) What is meant by the term hydrocarbon?

[1]

12306 7 [Turn over


(b) The IUPAC names of some hydrocarbons are given below.

ethene octane hex-2-ene

pentane propane but-1-ene

(i) Write the names of all the hydrocarbons from the table which aresaturated.

[1]

(ii) Draw the skeletal formula of hex-2-ene.

[1]

(iii) Hex-2-ene forms cis-trans isomers. Draw the two isomers in theboxes below and label them appropriately as cis and trans.

[3]

12306 8


(iv) Hex-2-ene reacts with hydrogen. State the catalyst used in thisreaction and give the name of the organic product formed.

Catalyst:

Product: [2]

(v) Draw the structural formula and state the IUPAC name of onebranched chain isomer of pentane.

IUPAC name: [2]

(vi) Write a balanced symbol equation for the combustion of pentanein a plentiful supply of air.

[2]

(c) A sample of 1.16 g of a hydrocarbon contains 0.96 g of carbon. Therelative molecular mass of the hydrocarbon is 58. The empiricalformula and molecular formula of the hydrocarbon may be determinedusing the data.

(i) What is meant by the terms empirical formula and molecularformula?

Empirical formula

Molecular formula

[2]

12306 9 [Turn over


(ii) Determine the empirical formula of the hydrocarbon.

Empirical formula = [3]

(iii) Determine the molecular formula of the hydrocarbon.

Molecular formula = [2]

(iv) Name the homologous series to which the hydrocarbon belongs.Explain your answer.

[2]

12306 10


4 Poly(chloroethene) and nylon are polymers.

(a) What is meant by the term polymer?

[2]

(b) Part of the structure of poly(chloroethene) is shown below.

(i) Draw the structure of the monomer from which poly(chloroethene)is formed.

[1]

(ii) State the type of polymerisation which occurs in formingpoly(chloroethene).

[1]

(iii) State one way in which polymer waste is disposed of and explainone advantage of this method of disposal.

[2]

12306 11 [Turn over


(c) The diagram below shows the reaction between hexanedioic acid andhexane-1,6-diamine. Continued reaction would produce the polymernylon-6,6.

(i) State the type of polymerisation which occurs to form nylon-6,6.

[1]

(ii) Suggest why the polymer is known as nylon-6,6.

[2]

(iii) This type of polymerisation may be reversed when the polymerreacts with water. Suggest the name of this type of reaction.

[1]

12306 12


5 Ethanol is a recreational drug and is the main component in alcoholic drinks. Aspirin is a pharmaceutical drug. Ethanol in alcoholic drinks is manufactured by fermentation whereas aspirin may be manufactured from salicylic acid and ethanoic anhydride.

(a) Explain the process of fermentation including the starting materials,conditions required and any other products formed.

You will be assessed on the quality of your writtencommunication.

[6]

12306 13 [Turn over


(b) The reaction below shows the production of aspirin from salicylic acidand ethanoic anhydride. The molecular formula of salicylic acid isC7H6O3 and its relative formula mass is 138.

salicylic acid ethanoic anhydride aspirin ethanoic acid

(i) Write the molecular formula of aspirin.

[1]

(ii) Calculate the relative formula mass of aspirin.

[1]

(iii) In a laboratory experiment 2.25 g of aspirin was obtained.Calculate the number of moles of aspirin obtained.

Moles of aspirin = [1]

(iv) State the number of moles of ethanoic anhydride required toproduce this number of moles of aspirin.

Moles of ethanoic anhydride = [1]

12306 14


(v) During this reaction 0.024 moles of ethanoic anhydride wereused. Using your answer to (b)(iv), calculate the percentage ofethanoic anhydride which reacted. Give your answer to 1 decimalplace.

Percentage of ethanoic anhydride = % [2]

(vi) Suggest one reason why not all the ethanoic anhydride reacted.

[1]

(c) An impure sample of aspirin is purified using the following method.

Dissolve the sample of aspirin in a minimum volume of hot solventto increase yield. Filter the mixture through filter paper. Allow thefiltrate to cool and crystallise. Filter off the crystals using suctionfiltration. Dry the crystals and determine their melting point. A purelaboratory sample of aspirin will melt at 139 °C.

(i) State a reason why dissolving the sample of aspirin in a minimumvolume of hot solvent increases yield.

[1]

12306 15 [Turn over


(ii) Draw a labelled diagram of the assembled apparatus used forsuction filtration.

[4]

(iii) State two reasons why suction filtration is used rather than gravityfiltration for the second filtration.

1.

2.

[2]

(iv) Suggest two ways the melting point would be different if therewere impurities in the sample of aspirin.

1.

2.

[2]

12306 16


6 Alcohols can be oxidised to aldehydes, ketones and carboxylic acids depending on the alcohol and the conditions used.

(a) Some oxidation reactions of alcohols are shown below where [O]represents a suitable oxidising agent.

Reaction 1:

Substance A Substance B

Reaction 2:

Substance C Substance D

Reaction 3:

Substance E Substance F

(i) Name a suitable oxidising agent to carry out the oxidationreactions of alcohols. State the colour change observed when thereaction occurs.

[3]

(ii) State the IUPAC names of substances B, D and F.

B

D

F [3]

(iii) Draw the skeletal formula for substance D.

[1]

12306 17 [Turn over


(b) The mass spectrum shown below was obtained for one of thesubstances A, C or E. The peaks occur at mass values which showthe relative formula mass of the molecule and its fragments.

100

80

60

40

20

0.0

10 20 30 40 50mass

relative abundance / %

Identify which substance A, C or E would produce this spectrum and explain your answer.

[2]

Source: Adapted - Reprinted courtesy of the National Institute of Standards and Technology, U.S. Department of Commerce. Not copyrightable in the United States

12306 18


(c) The following infrared (IR) spectrum was obtained from one of thesubstances A, B, C, D, E or F.

100

80

60

40

20

4000 3500 3000 2500 2000 1500 1000 500wavenumber / cm−1

transmittance / %

Using the table below identify which substance (A, B, C, D, E or F) would produce this spectrum and explain your answer.

Wavenumber (cm−1) Bond

750 – 1100 C—C (alkanes, alkyl groups)

1000 – 1300 C—O (alcohols, carboxylic acids)

1650 – 1800 C O (carboxylic acids, aldehydes, ketones)

2500 – 3200 O—H (carboxylic acids)

2750 – 2850 C—H (aldehydes)

2850 – 3000 C—H (alkanes, alkyl groups, alkenes)

3200 – 3600 O—H (alcohols)

[2]

——

Graph – Spectrum 1 from © Inspirational chemistry – resources for modern curricula by Vicky Wong. Chapter 7, Analysis, 7.5 Spectroscopy, page 185. Published by the Royal Society of Chemistry, 2006. https://pubs.rsc.org/en/content/ebook/978-0-85404-399-6

THIS IS THE END OF THE QUESTION PAPER

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