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© Mana Tohu Mātauranga o Aotearoa, 2012. Pūmau te mana.Kia kaua rawa he wāhi o tēnei tuhinga e tāruatia ki te kore te whakaaetanga a te Mana Tohu Mātauranga o Aotearoa.

MĀ TE KAIMĀKA ANAKE

TAPEKE

Te Mātauranga Matū, Kaupae 2, 201291165M Te whakaatu māramatanga ki ngā āhuatanga o

ngā matūwaro kua tīpokahia

9.30 i te ata Rātū 20 Whiringa-ā-rangi 2012 Whiwhinga: Whā

Paetae Paetae Kaiaka Paetae KairangiTe whakaatu māramatanga ki ngā āhuatanga o ngā matūwaro kua tīpokahia.

Te whakaatu māramatanga hōhonu ki ngā āhuatanga o ngā matūwaro kua tīpokahia.

Te whakaatu māramatanga matawhānui ki ngā āhuatanga o ngā matūwaro kua tīpokahia.

Tirohia mehemea e ōrite ana te Tau Ākonga ā-Motu (NSN) kei tō pepa whakauru ki te tau kei runga ake nei.

Me whakautu e koe ngā pātai KATOA kei roto i te pukapuka nei.

He taka pūmotu kua whakaritea ki te Pukaiti Rauemi L2-CHEMMR.

Ki te hiahia koe ki ētahi atu wāhi hei tuhituhi whakautu, whakamahia te wāhi wātea kei muri i te pukapuka nei.

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

HOATU TE PUKAPUKA NEI KI TE KAIWHAKAHAERE HEI TE MUTUNGA O TE WHAKAMĀTAUTAU.

SUPERVISOR’S USE ONLY

See back cover for an English translation of this cover

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Te Mātauranga Matū 91165M, 2012

MĀ TE KAIMĀKA

ANAKE

Kia 60 meneti hei whakautu i ngā pātai o tēnei pukapuka.

PĀTAI TUATAHI

(a) HewaiwaihāētahipoinanahahangangaewhāoteC4H10O.Kuatātuhiatētahioēneipoinanahametewhakaingoakitetūtohiiraronei.

WhakaotihiatetūtohiheiwhakaatuitetātaihangangamengāingoaIUPAC(nahanaha)oētahiatuongāpoinanahahanganga.

H C C C C OH

H H H H

H H HH

waihā-1-pūwaro

You are advised to spend 60 minutes answering the questions in this booklet.

QUESTION ONE

(a) FourofthestructuralisomersofC4H10Oarealcohols.Oneoftheseisomershasbeendrawnandnamedforyouinthetablebelow.

CompletethetabletoshowthestructuralformulaeandIUPAC(systematic)namesoftheotherstructuralisomers.

H C C C C OH

H H H H

H H HH

butan-1-ol

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Chemistry 91165, 2012

ASSESSOR’S USE ONLY

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MĀ TE KAIMĀKA

ANAKE

(b) Kataeateōhikitewaihā-1-pūwarokiahuriheiwaikawawaro-waihā.

(i) Tuhiateingoa,tetātairāneiotētahikaiwhakahohetōtikakataeatewhakahaereitetauhohenga.

Whakauruangāāhuatangatauwhāiti.

(ii) Whakaahuahiatehuringataekakiteaake.

(iii) KataeaanōtētahiatuongāpoinanahawaiwaihāoteC4H10Oteōhikikiahuriheiwaikawawaro-waihā.

Tautohuatēneipoinanahamāteingoa,tetātaihangangarānei:

Whakamāramahiatōkōwhiringapoinanaha.

(b) Butan-1-olcanbeoxidisedtoformacarboxylicacid.

(i) Writethenameorformulaofasuitablereagentthatcouldbeusedtocarryoutthereaction.

Includeanyspecificconditions.

(ii) Describethecolourchangethatwouldbeobserved.

(iii) OneoftheotheralcoholisomersofC4H10Ocanalsobeoxidisedtoform acarboxylicacid.

Identifythisisomerbynameorstructuralformula:

Explainyourchoiceofisomer.

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MĀ TE KAIMĀKA

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(c) Metautohungāpātaraeruawhaiwaiwarorua1-pēwāro,CH3CH2CH2CH=CH2,meteowaro,CH3CH2CH2CH2CH2CH3.

Ewāteaanangākaiwhakahoheerua,arā,tewaipūkane,Br2,metekonurehupāporowhakawaikawa,MnO4

– / H+.

ArotakehiamēnākataeatewhakamahingākaiwhakahoheeRUAheiweheweheitewaiwarorua1-pēwarometeowaro.

Irotoitōwhakautumewhakauru:

• tētahiwhakaahuatangaongāmomotauhohengakapāmai

• ngāāhuatangakahiahiatia

• ngāmātakingakaputa

• ngāwhāriteewhakaatuanaitetātaihangangaote(ngā)kaiwhakahohewhaiwaromete(ngā)hua.

(c) Twobottlescontainingpent-1-ene,CH3CH2CH2CH=CH2,andhexane,CH3CH2CH2CH2CH2CH3,requireidentification.

Tworeagents,brominewater,Br2,andacidifiedpotassiumpermanganate,MnO4– / H+,

areavailable.

EvaluatethepossibleuseofBOTHreagentstodistinguishbetweenthepent-1-eneandhexane.

Inyouransweryoushouldinclude:

• adescriptionofthetypeofreactionsthatwouldoccur

• anyconditionsthatwouldberequired

• anyobservationsthatwouldbemade

• equationsshowingthestructuralformulaeoftheorganicreactant(s)andproduct(s).

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MĀ TE KAIMĀKA

ANAKE

PĀTAI TUARUA

(a) WhakaotihiatetūtohiewhaiakeneiheiwhakaatuitetātaihangangameteingoaIUPAC (nahanaha)mōiapūhui.

Tātai hanganga Ingoa

H3C C CH3

Cl

Cl

waikawaewaro

H C C C C C OH

O

Br H H CH3

H H HH

N CH3 H

H

2-aminopēwaro

QUESTION TWO

(a) CompletethefollowingtabletoshowthestructuralformulaandIUPAC(systematic)nameforeachcompound.

Structural formula Name

H3C C CH3

Cl

Cl

ethanoicacid

H C C C C C OH

O

Br H H CH3

H H HH

N CH3 H

H

2-aminopentane

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MĀ TE KAIMĀKA

ANAKE

(b) Tuhiamaimepēheateweheweheiwaengaiteaminopūwaro,CH3CH2CH2CH2NH2,metewaikawapūwaro,CH3CH2CH2COOH,mātewhakamahipepatohuwaikawahaukū.

Homaitētahipūtakemōtōwhakautu.

(c) Inatauhoheatewaikawapūwarokitekonutaihauwaipākawawaro,NaHCO3,kakiteatekoropupūitewāotetauhohenga.

(i) Heahatemomotauhohengakeiteputa?

(ii) Whakamāramahiaheahaikiteaaitekoropupūitewāotetauhohenga.

(iii) Whakaotiatewhāriteiraroneiheiwhakaatuitetātaihangangaotehuawhaiwarokuaputa.

H C C C CO H

O+ NaHCO3

H H H

H HH

(b) Statehowyoucoulddistinguishbetweenaminobutane,CH3CH2CH2CH2NH2,andbutanoicacid,CH3CH2CH2COOH,usingdamplitmuspaper.

Giveareasonforyouranswer.

(c) Whenbutanoicacidreactswithsodiumhydrogencarbonate,NaHCO3,fizzingcanbeseenduringthereaction.

(i) Whattypeofreactionisoccurring?

(ii) Explainwhyfizzingisobservedduringthereaction.

(iii) Completetheequationbelowtoshowthestructuralformulaoftheorganicproductformed.

H C C C CO H

O+ NaHCO3

H H H

H HH

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MĀ TE KAIMĀKA

ANAKE

(d) Katauhoheteewarohaumāota,CH3CH2Cl,kiteKOHwaiwai,teKOHwaiwaihā,meteNH3.

Whakatauriteangātauhohengaoteewarohaumāotakingākaiwhakahoheetoru.


• temomotauhohengametetakeiwhakarōpūhiaaiheitauamomo

• temomorōpūmahingaiputa

• ngāwhāriteewhakaatuanaingātātaihangangamōngātauhohengaetūponoana.

(d) Chloroethane,CH3CH2Cl,reactswithaqueousKOH,alcoholicKOH,andwithNH3.

Compareandcontrastthereactionsofchloroethanewiththethreereagents.


• thetypeofreactionoccurringandthereasonwhyitisclassifiedasthattype

• thetypeoffunctionalgroupformed

• equationsshowingstructuralformulaeforreactionsoccurring.

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ANAKE

PĀTAI TUATORU

Ewhakamahiaanatewaiwarorua-1-pūwaroiteraupapatauhohengairaronei.

CH3CH2CH=CH2

A

B

C

D

CH3CH2CH2CH3

F

CH3CH2CHCH3

E

Clme te

Tauhohenga 2

Tauhohenga 1

H 2O / H

+

whakawairautanga Tauhohenga 4

Tauhohenga 3

(a) (i) Tātuhiakiaruangāwaetāruaruaotewaerau,B,ihangaiaiteTauhohenga 1.

(ii) Homaiteingoa,tetātairāneiotētahikaiwhakahohetōtikaiteTauhohenga 4; whakauruangāāhuatangatauwhāitiehiahiatiaana.

(iii) Homaiteingoa,tetātairāneiotētahikaiwhakahohetōtikaiteTauhohenga 3; whakauruangāāhuatangatauwhāitiehiahiatiaana.

(b) KataeaetepūhuiAtetīariheipoinanaha(cis-trans)āhuahanga?

Parahautiatōwhakautu,metekōreromōngāwhakaritengamōngāpoinanaha(cis-trans) āhuahanga.

QUESTION THREE

But-1-eneisusedinthereactionsequenceshownbelow.

CH3CH2CH=CH2

A

B

C

D

CH3CH2CH2CH3

F

CH3CH2CHCH3

E

Cland

Reaction 2

Reaction 1

H 2O / H

+

polymerisation Reaction 4

Reaction 3

(a) (i) Drawtworepeatingunitsofthepolymer,B,formedinReaction 1.

(ii) GivethenameorformulaofasuitablereagentinReaction 4;includeanyspecificconditionsrequired.

(iii) GivethenameorformulaofasuitablereagentinReaction 3;includeanyspecificconditionsrequired.

(b) CancompoundAexistasgeometric(cis-trans)isomers?

Justifyyouranswer,includingreferencetotherequirementsforgeometric(cis-trans) isomers.

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ANAKE

(c) (i) TātuhiangātātaihangangaongārāpoingotawhaiwaroCmeD,ihangaiaiteTauhohenga 2,kingāpouakairaronei.

C D

(ii) ĀtawhakamāramatiatetautohengaiteTauhohenga 2.


• tetautohungaongāhuamātāmua,mātāmurihoki

• tētahiwhakamāramamōtetakeeruapeangāhuakaputa

• heparahautangaotōwhakatauingāhangangarerekēkingāpouakaCmeDmetekōreromōteraupapatauhohenga.

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MĀ TE KAIMĀKA

ANAKE

(c) (i) DrawthestructuralformulaeoftheorganicmoleculesCandD,formedinReaction 2,intheboxesbelow.

C D

(ii) ElaborateonthereactionoccurringinReaction 2.


• identificationofthemajorandminorproducts

• anexplanationofwhytherearetwopossibleproducts

• justificationofyourplacementofthedifferentstructuresinboxesCandDwithreferencetothereactionsequence.

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MĀ TE KAIMĀKA

ANAKETAU PĀTAI

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

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QUESTION NUMBER

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

© New Zealand Qualifications Authority, 2012. 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, 201291165 Demonstrate understanding of the properties of

selected organic compounds

9.30 am Tuesday 20 November 2012 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 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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