Te Mātauranga Matū, Kaupae 2, 2014€¦ · 4 no reaction CH 3 CH 2 NH + CH 3 CH CH 2 Compare and...

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Te Mātauranga Matū, Kaupae 2, 201491165M Te whakaatu māramatanga ki ngā āhuatanga o

ētahi matūwaro

2.00 i te ahiahi Rātū 11 Whiringa-ā-rangi 2014 Whiwhinga: Whā

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Tirohia mehemea kei roto nei ngā whārangi 2 – 21 e raupapa tika ana, ā, kāore hoki he whārangi wātea.

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Te Mātauranga Matū 91165M, 2014

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PĀTAI TUATAHI

(a) Kingāpouakairaro,tātuhiatētahiwaiwaihā1tuatahi,tuarua,tuatoruhokimōterāpoingotaC5H11OH.

Tuatahi Tuarua Tuatoru

(b) (i) Inaōhikitiangāwaiwaihātuatahietepāharekonupangowhakawaikawa,MnO4– / H+,

kaputamaikongāwaikawawaro-waihā(carboxylic).

Kitepouakairaro,tātuhiatewaiwaihātuatahiiōhikitiakiaputaaitewaikawawaro-waihāewhakaaturiaana.

CH3 CH

2 CH

2 CH

2 C OH

O

MnO4

– / H+

(ii) Kataeatewhakamahitekatotepāharekonupango,MnO4–,heiōhikiingāwaiwarorua.

Tātuhiatehuaotetauhohengaewhaiakeana:

CH3 CH

2 CH

2 CH

2 CH CH

2

MnO4

–

1waipiro

2

QUESTION ONE

(a) Intheboxesbelow,drawaprimary,asecondary,andatertiaryalcoholforthemoleculeC5H11OH.

Primary Secondary Tertiary

(b) (i) Whenprimaryalcoholsareoxidisedbyacidifiedpermanganate,MnO4– / H+,theyform

carboxylicacids.

Intheboxbelow,drawtheprimaryalcoholthatwasoxidisedtoformthecarboxylicacidshown.

CH3 CH

2 CH

2 CH

2 C OH

O

MnO4

– / H+

(ii) Permanganateion,MnO4–,canbeusedtooxidisealkenes.

Drawtheproductofthefollowingreaction:

CH3 CH

2 CH

2 CH

2 CH CH

2

MnO4

–

3

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(c) Ewhakarōpūhiakatoatiaanangātauhohengaewhakaaturiaanairaronōtemomotauhohengakotahi.

Tauhohenga Tuatahi

Kahoheteowaro,CH3CH2CH2CH2CH2CH3,kitewaipūkane,Br2(waiwai)

Tauhohenga Tuarua

Kahohetewaihā-1-owaro,CH3CH2CH2CH2CH2CH2OH,kitePCl3

Tauhohenga Tuatoru

Kahohete1-owaropūhaumāota,CH3CH2CH2CH2CH2CH2Cl,kiteNH3 kukū(waiwaihā)

Whakatauriteaēneitauhohenga.

Itōwhakautu,me:

• tuhimēnāehiahiatiaanaētahiāhuatanga

• whakaahuatemomotauhohengakaputametewhakamāramahokiitetakeewhakarōpūhiakatoatiaanangātauhohengaetorukitēneimomotauhohenga

• whakamāramaheahaiputaaingāpapatūrangaeruaiteTauhohenga Tuatahi.

4

(c) Thereactionsshownbelowareallclassifiedasbeingthesametypeofreaction.

Reaction One hexane,CH3CH2CH2CH2CH2CH3,reactswithbrominewater,Br2(aq)

Reaction Two hexan-1-ol,CH3CH2CH2CH2CH2CH2OH,reactswithPCl3

Reaction Three 1-chlorohexane,CH3CH2CH2CH2CH2CH2Cl,reactswithconcNH3(alc)

Compareandcontrastthesereactions.

Inyouransweryoushould:

• statewhetheranyconditionsarerequired

• describethetypeofreactionoccurringandexplainwhyallthreereactionsareclassifiedasthistypeofreaction

• explainwhytwolayersforminReaction One.

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MĀ TE KAIMĀKA

ANAKE

PĀTAI TUARUA

(a) Whakaotiatetūtohiiraroneiheiwhakaatuiteturetātaihangangameteingoa(nahanaha)IUPACmōiapūhui.

Ture tātai hanganga Ingoa (nahanaha) IUPAC

Waiwarotoru-1-pōwaro

2,2-waihā-1-pēwaropūhaumāota-rua

CH3 CH

2 CH

2 CH

2 CH

2 NH

2

CH3 CH

2 CH

2 CH CH

2 C OH

OCH3

CH3 CH CH C CH

2 CH

3

Cl Cl

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QUESTION TWO

(a) CompletethefollowingtabletoshowthestructuralformulaandIUPAC(systematic)nameforeachcompound.

Structural formula IUPAC (systematic) name

But-1-yne

2,2-dichloropentan-1-ol

CH3 CH

2 CH

2 CH

2 CH

2 NH

2

CH3 CH

2 CH

2 CH CH

2 C OH

OCH3

CH3 CH CH C CH

2 CH

3

Cl Cl

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(b) Kuawhakaaturiairaroneingāhangangaongāpūhuiwhaiwaroetoru.

PūhuiA CH3 CH

2 CH CH CH

3

PūhuiB CH3 CH

2 CH

2 CH CH

2

PūhuiC CH3 CH

2 CH

2 CH

2 CH

3

WhakamāramahiatetakekataeaetepūhuiA tenohoheipoinanahaāhuahanga(cismetrans),engarikāoreetaeaeBmeC.

Itōwhakautu,me:

• tātuhingāpoinanaha(cismetrans)āhuahangaotepūhuiAirotoingāpouakairaro

• whakamāramangāwhakaritengamōngāpoinanaha(cismetrans)āhuahangamātekōreromōngāpūhuiA,B,meC.

poinanahacis poinanaha trans

8

(b) Thestructuresofthreeorganiccompoundsareshownbelow.

CompoundA CH3 CH

2 CH CH CH

3

CompoundB CH3 CH

2 CH

2 CH CH

2

CompoundC CH3 CH

2 CH

2 CH

2 CH

3

ExplainwhycompoundA canexistasgeometric(cisandtrans)isomers,butcompoundsB andCcannot.


• drawthegeometric(cisandtrans)isomersofcompoundAintheboxesbelow

• explaintherequirementsforgeometric(cisandtrans)isomersbyreferringtocompoundsA,B,andC.

cisisomer transisomer

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He wāhi anō mō tō whakautu ki tēnei pātai kei te whārangi 12.


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(c) Katāpirihiatekonutaipākawawaro,tewaikawapūhaumāota,metewaikawapungatarakingātīpakongarerekēongāpūhuiwhaiwaroetoru.

Keitetūtohiorarongāhangangaongāpūhuimengāhuaongātauhohenga.

Whakahohe

Pūhui whaiwaroCH

3 CH

2 C OH

O

CH3 CH

2 CH

2 NH

2CH

3 CH

2 CH

2 OH

Na2CO3 (i) kāorehetauhohenga kāorehetauhohenga

HCl kāorehetauhohenga (ii) CH3 CH

2 CH

2 Cl

H2SO4 kāorehetauhohenga CH3 CH

2 CH

2 NH

3

+ CH3 CH CH

2

Whakatauriteangātauhoheka hua maiiwaengaiēneipūhuiwhaiwaromengāwhakahohekitetūtohiirungaake.

Itōwhakautu,me:

• homaitehangangaongāhuawhaiwaro(i)me(ii)

• whakaahuangāmomotauhohengarerekēkahuamai,kahomaiingātakeewhakarōpūhiaanakitauamomo

• tautohungāmomoāhuatangaehiahiatiaanakiahuamaiaingātauhohenga.

10

(c) Sodiumcarbonate,hydrochloricacid,andsulfuricacidareeachaddedtoseparatesamplesofthreeorganiccompounds.

Thestructuresofthecompoundsandtheproductsofanyreactionsaregiveninthetablebelow.

Reagent

Organic compoundCH

3 CH

2 C OH

O

CH3 CH

2 CH

2 NH

2CH

3 CH

2 CH

2 OH

Na2CO3 (i) noreaction noreaction

HCl noreaction (ii) CH3 CH

2 CH

2 Cl

H2SO4 noreaction CH3 CH

2 CH

2 NH

3

+ CH3 CH CH

2

Compareandcontrastthereactionsthatdooccurbetweentheseorganiccompounds,andthereagentsinthetableabove.


• givethestructureoftheorganicproducts(i)and(ii)

• describethedifferenttypesofreactionsoccurring,andgivereasonswhytheyareclassifiedasthattype

• identifyanyspecificconditionsthatarerequiredforthereactionstooccur.

There is more space for your answer to this question on page 13.

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PĀTAI TUATORU

Ewhakaaturiaanatētahimaheretauhoheiraro.

CH3 CH

2 CH

2 CH CH

2

CH3 CH

2 CH

2 CH CH

3

Cl

CH3 CH

2 CH CH CH

3

C C C C

CH3 CH

2 CH

2 CH

2 CH

2

Cl

C2H

5

CH3

HCl

KOH (alc)

KOH (alc)

(major product) (minor product)

(minor product)

polymerisation reaction


two repeating units

Reaction 1

Reaction 2

Reaction 3

Reaction 4

A

C D

B

Reaction 5

H

H CH3

H

C2H

5H

Tauhohenga 1

Tauhohenga 4

Tauhohenga 3Tauhohenga 5

(huanui) (huaiti)

(huaiti)

tauhohengawhakawaerautanga

KOH(waiwaihā)

tauhohengawhakawaerautanga

ngāwaetāruaruaerua

Tauhohenga 2

KOH (waiwaihā)

(a) (i) Whakamāramahiatetakemaiitemaheretauhoheewhakaaturiaanaanōiraro,ewhakarōpūhiaanateTauhohenga 1heitauhohengatāpiri.

CH3 CH

2 CH

2 CH CH

2

CH3 CH

2 CH

2 CH CH

3

Cl

CH3 CH

2 CH

2 CH

2 CH

2

Cl

HCl


Reaction 1

A B(huanui) (huaiti)

Tauhohenga 1

14

QUESTION THREE

Areactionschemeisshownbelow.

CH3 CH

2 CH

2 CH CH

2

CH3 CH

2 CH

2 CH CH

3

Cl

CH3 CH

2 CH CH CH

3

C C C C

CH3 CH

2 CH

2 CH

2 CH

2

Cl

C2H

5

CH3

HCl

KOH (alc)

KOH (alc)


(minor product)



two repeating units

Reaction 1

Reaction 2

Reaction 3

Reaction 4

A

C D

B

Reaction 5

H

H CH3

H

C2H

5H

(a) (i) ExplainwhyReaction 1fromthereactionscheme,shownagainbelow,isclassifiedasanadditionreaction.

CH3 CH

2 CH

2 CH CH

2

CH3 CH

2 CH

2 CH CH

3

Cl

CH3 CH

2 CH

2 CH

2 CH

2

Cl

HCl


Reaction 1

A B

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ANAKE

(ii) WhakamāramahiatetakekotepūhuiAtehuamatuamōteTauhohenga 1ewhakaaturiaanaitemaheretauhoheitewhārangiomuaake.

(b) (i) Whakamāramahiatetakemaiitemaheretauhoheewhakaaturiaanaanōiraro,ewhakarōpūhiaanateTauhohenga 2heitauhohengatangohanga.

CH

3 CH

2 CH CH CH

3

KOH (alc)

(minor product)

Reaction 2

C D

CH3 CH

2 CH

2 CH CH

3

Cl

Tauhohenga 2

KOH (waiwaihā)

(huaiti)

(ii) HetauhohengatangohangaanōteTauhohenga 4.

TātuhiatetātaihangangaotehuakaputaiteTauhohenga 4.

(c) (i) TātuhiangāwaetāruaruaeRUAotewaeraukaputaiteTauhohenga 5.

Ka haere tonu te Pātai Tuatoru i te whārangi 18.

16

(ii) ExplainwhycompoundAisthemajorproductforReaction 1showninthereactionschemeonthepreviouspage.

(b) (i) ExplainwhyReaction 2fromthereactionscheme,shownagainbelow,isclassifiedasaneliminationreaction.

CH

3 CH

2 CH CH CH

3

KOH (alc)

(minor product)

Reaction 2

C D

CH3 CH

2 CH

2 CH CH

3

Cl

(ii) Reaction 4isalsoaneliminationreaction.

DrawthestructuralformulaoftheproductformedinReaction 4.

(c) (i) DrawTWOrepeatingunitsofthepolymerformedinReaction 5.

17



Question Three continues on page 19.


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ANAKE

(ii) WhakatauriteatewaeraukaputaiteTauhohenga 5kitewaeraukaputaiteTauhohenga 3.

Itōwhakautumewhakamāramaekoeheahairerekēaingāwaeraukaputaiēneitauhohengaerua.

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(ii) CompareandcontrastthepolymerformedinReaction 5tothepolymerformedinReaction 3.

Inyouransweryoushouldexplainwhythepolymersformedinthesetworeactionsaredifferent.

19




MĀ TE KAIMĀKA

ANAKETAU PĀTAI

He puka anō mēnā ka hiahiatia.Tuhia te (ngā) tāu pātai mēnā e hāngai ana.

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21



QUESTION NUMBER

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© New Zealand Qualifications Authority, 2014. All rights reserved.No part of this publication may be reproduced by any means without the prior permission of the New Zealand Qualifications Authority.

Level 2 Chemistry, 201491165 Demonstrate understanding of the properties of

selected organic compounds

2.00 pm Tuesday 11 November 2014 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–CHEMMR.

If you need more space for any answer, use the page(s) provided at the back of this booklet and clearly number the question.

Check that this booklet has pages 2 – 21 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.

English translation of the wording on the front cover

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Te Mātauranga Matū, Kaupae 2, 2014€¦ · 4 no reaction CH 3 CH 2 NH + CH 3 CH CH 2 Compare and...

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