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Level 2 Chemistry, 201791165 Demonstrate understanding of the properties of

selected organic compounds

2.00 p.m. Thursday 16 November 2017 Credits: Four

Achievement Achievement with Merit Achievement with ExcellenceDemonstrate understanding of the properties of selected organic compounds.

Demonstrate in-depth understanding of the properties of selected organic compounds.

Demonstrate comprehensive understanding of the properties of selected organic compounds.

Check that the National Student Number (NSN) on your admission slip is the same as the number at the top of this page.

You should attempt ALL the questions in this booklet.

A periodic table is provided on the Resource Sheet L2–CHEMR.

If you need more room for any answer, use the extra space provided at the back of this booklet and clearly number the question.

Check that this booklet has pages 2 –12 in the correct order and that none of these pages is blank.

YOU MUST HAND THIS BOOKLET TO THE SUPERVISOR AT THE END OF THE EXAMINATION.

QUESTION ONE

(a) Polyvinylchloride(polychloroethene)isoftenusedtomakeartificialleather.Thiscanthenbeusedtocoverchairs,covercarseats,andmakeclothing.

Asectionofapolyvinylchloridemoleculeisshownbelow.

~ C C C C C C ~

H H H H H H

H Cl H Cl H Cl

(i) Drawthemonomerfromwhichthepolymerpolyvinylchloridewouldbemade.

(ii) Explain the difference in the structures and chemical reactivity of the monomer and polymer,andwhythedifferenceisimportantfortheusesofthepolymer.

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(iii) Making polyvinyl chloride (polychloroethene) from its monomer is called ‘addition polymerisation’.

Explaintheterm‘additionpolymerisation’usingpolyvinylchlorideasanexample.

Includeanequationinyouranswer.

Equation:

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(b) Achemistryclasswaslearningaboutthechemistryofhaloalkanes.Theywereresearchingtheeffectofheatandconcentratedpotassiumhydroxideinethanol,conc.KOH(alc),onthehaloalkane 2-chloropropane.

(i) Drawtheorganicproductformedinthefollowingreaction.

CH3CH CH3

Cl

conc. KOH(alc)

heat

(ii) Explainhowthefunctionalgroupoftheorganicproductdrawnabovecouldbeidentified.

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(iii) 2-bromo-3-methylbutanealsoreactswithconc.KOH(alc).However,inthisreactionTWOorganicproductsareformed,amajorandaminorproduct.

Giveanaccountofthechemicalprocessesthatoccurinthisreaction.

In your answer you should:

• write an equation for this reaction showing the organic compounds

• name the type of reaction occurring

• explain how the products form

• explainwhichproductyouwouldexpecttobetheminorproduct.

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QUESTION TWO

(a) Thestructureofamoleculeofanorganiccompound,threonine,isshownbelow.

H C OH

H

H2N C COOH

CH3

threonine

alcohol functional group

Analcoholfunctionalgrouphasbeenidentifiedinthethreoninemoleculeabove.

(i) Circle and name two otherfunctionalgroupsonthethreoninemoleculeabove.

(ii) Classifythealcoholfunctionalgroupasprimary,secondary,ortertiary.

(iii) Explainhowyouclassifiedthealcoholgroup.

(b) Nametheorganiccompoundsinthetablebelow.

Compound IUPAC (systematic) name

CH3 CH2 CH2 C CH

CH3 CH CH CH2 CH2 CH3

Br CH3

CH3 CH2 CH C CH3

CH3

OH CH3

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(c) (i) Draw four alkene isomers for the organic compound C4H8inthetablebelow.

1. 2.

3. 4.

(ii) Identify the compounds that are cis and trans(geometric)isomersfromthetableabove.

cis trans

Number

Justify your choices, and explain why only these two compounds are cis and trans (geometric)isomers.

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(d) Alkanesandalkenescanbeidentifiedbytheirreactionswithasolutionofbrominewater,Br2(aq).

Contrast the types of reactions an alkane and an alkene will undergo with an orange solution ofbrominewater.

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QUESTION THREE

(a) (i) Completethefollowingreactionschemebydrawingthestructuralformulaefortheorganic compounds A, C, and D, and identifying reagents 2 and 3.

C C

H

H H

H

Compound A

Compound B

Compound C

Reagent 1

H2O / H+

Reagent 2

CH3COOH

CH3CH2NH2

Compound D

Reagent 4

Cl2 / UV light

Reagent 3

Compound E

Reagent 5

NH3(alc)

(ii) Identify the types of reactions that occur to produce compounds A, B, C, D, and E:

A.

B.

C.

D.

E.

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(b) DescribeasimpletestthatwilldistinguishbetweensolutionsofthefinalorganiccompoundsB and E.

(c) Compounds B and Ereacttogether.

(i) WriteabalancedequationforthereactionthatoccursbetweencompoundsB and E.

(ii) IdentifythetypeofreactionthatoccursbetweencompoundsB and E.

Justifyyouranswer.

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(d) Explain how compound Afromthereactionschemecouldbedirectlyconvertedintocompound D.

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QUESTION NUMBER

Extra paper if required.Write the question number(s) if applicable.