A STRATEGY TO ENHANCE CONCEPTUAL ......Project Aim 1 – Design a template for using active learning that could be applied across disciplines. The first aim was to develop and refine

LITE 2017 Teaching Excellence Project Leader Report

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LEEDS INSTITUTE TEACHING EXCELLENCE

for

A STRATEGY TO ENHANCE CONCEPTUAL UNDERSTANDING USING ACTIVE LEARNINGProject Report

Nimesh Mistry

PATRICKSON | Mobilising the curriculum

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LITE creates a sector-leading community of excellence in teaching practice and scholarship.

Join the discussion: @leedsteaching teachingexcellence.leeds.ac.uk

|Astrategytoenhanceconceptualunderstandingusingactivelearning

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TableofcontentsExecutivesummary 5Listoftablesandfigures 61.Introduction 7 1.1Howimportantisthediscipline-specificpedagogydomain? 82.Projectaims 9 2.1Activelearningtemplate 9 2.2Aims 103.Methodology 12

3.1Methodstomeasureconceptualunderstanding 12 3.2Designanddeliveryofdiagnostictests 13

3.3Methodforanalysingdiagnostictests 14 3.3.1Interpretation 14

3.3.2Codingandscoring 15 3.3.3Rankingandclustering 15 3.3.4Clusteranalysis 15 3.3.5Cross-sectionalanalysis 15 3.4Validationofthemethodology 154.Reactivitytopic|resultsanddiscussion 16 4.1OrganicChemistry 16 4.2ResultsfromtheReactivitydiagnostictests 16 4.3Designingactivelearningworkshopsfortertiarylevelconcepts 17 4.4Deliveringactivelearningworkshopsfortertiarylevelconcepts 18 4.5Determiningthesuccessoftheactivelearningworkshops 19 4.6SummaryoftheactivelearningstrategyappliedtoReactivity 195.MolecularShapetopic|resultsanddiscussion 20 5.1MolecularShape(stereochemistry) 20 5.2ResultsfromMolecularShapediagnostictests 20 5.3Developingactivelearningresourcesfor3Dspatialreasoning 21 5.4Creatingafreeonlinetooltotranslatebetween2Dand3D representations 21 5.5CreatingatextbooktoteachMolecularShape 226.Conclusions 23 6.1Futurework 23

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References 25Appendices 27 AppendixA|SummaryofconceptsusedforbothReactivityand MolecularShapediagnostictests § 27 AppendixB|Exampleoftheanalysismethodology 28 AppendixC|ResultsfromReactivitydiagnostictests 29 AppendixD|Timelineofprojectobjectivesandimpact 30 AppendixE|Summaryofprojectdissemination 31Abouttheauthorandacknowledgements 32


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ExecutivesummaryOverview

AstudybyFreeman(2014)showedthatactivelearninginSTEMsubjectsleadstohighergradesand

lower failure rates. However, active learning is only successful when challenging students’

misconceptionsaboutscientificphenomena(OrtizandHeron2005;HunterandHeron2013).

Thisprojectaimstodevelopastrategyforusingactivelearningthattranslatesacrossdisciplinesand

can be applied in different teaching environments. The key feature of this strategy is that it first

identifiesstudentmisconceptionsofagiventopic,thenusesanactivelearningactivitythatspecifically

challenges those misconceptions (below). The context for this study was organic chemistry (the

chemistryofcarbon-basedmolecules).

Activelearningtemplatetoimproveconceptualunderstanding

Keyfindings

• Students relyon simpler concepts they learn in secondaryeducation to solveproblems in

chemistry.

• Activelearningapproachestoteachmorecomplicatedconceptsintertiaryeducationshould

firstexposethelimitationsofsimplermodelsfromsecondaryeducation.

• Studentsemployalgorithmicapproacheswhenusingspatialreasoningtotranslatebetween

2Dand3Drepresentationsofmolecules.

• Activelearningapproachestoteachspatialreasoningcontainexplicitinstructionsofhowto

use3Dmodelstotranslatebetweenrepresentations.

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ListoftablesandfiguresFigure1|Domainsofactivelearning 7Figure2|Studentmisconceptionsaboutbalancingobjects 8Figure3|Activelearningtemplatetoimproveconceptualunderstanding 9Figure4|Exampleoforganicmoleculesreacting 10Figure5|Exampleofanorganicmoleculein3dimensions 11Figure6|Summaryofhowdiagnostictestsweredelivered 13Figure7|Studentsmusttranslatebetween2Dand3Drepresentations 20Figure8|Exampleofanalysismethodologyappliedtoquestion1of

Reactivitytest 28Table1|Summaryofmethodsusedtodiagnosestudentlearning 12Table2|NumberofresponsesforbothReactivityandMolecularShapetests 14Table3|SummaryofconceptsusedinReactivitydiagnostictest 27Table4|SummaryofconceptsusedinMolecularShapediagnostictest 27Table5|Breakdownofconceptsineachquestionandwhethertheyaretaughtinsecondaryortertiaryeducation 29


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1.IntroductionActivelearningisaninstructionalmethodthatengagesstudentsintheirlearningduringclasstime.It

is considered to be a student-centred teaching method where students are required to perform

meaningfullearningactivitiesinthepresenceofateacher.Thisisincontrasttotraditionalformsof

teachingwheretheteacherwilldelivermaterialinadidacticformatwhilstthestudentsarepassive

recipientsofthisinformation.

AstudybyFreeman(2014)comparingtraditionaltoactive learningapproaches inSTEMeducation

found that active learning improved performance amongst all students. The improvement was

particularlyeffectivewiththelowerquartilewiththesestudents1.5timeslesslikelytofailasaresult

of active learning. Active learning also reduces the achievement gap between students from

disadvantagedandnon-disadvantaged students (HaakandFreeman,2011).Whilst researchactive

learningforthisproject,authorshavefoundthatmuchoftheexistingresearchcouldbegroupedinto

oneoffourdomains(Figure1).

Figure1:Domainsofactivelearning.

Thefirstdomainconsidersthelearningspacesthathavebeendevelopedtofacilitateactivelearning.

TheseincludeinteractivelecturetheatressuchasRogerStevenslecturetheatre18andMechanical

EngineeringlecturetheatreBattheUniversityofLeeds.Theseconddomainconsidersgenericmodels

foremployingactivelearningsuchastheflippedmodelandpeerinstruction.Thesearemodelsthat

considergeneralprinciplesofstudentlearningsuchasconstructivismwhichappliestoallstudents,

nomatterthesubjecttheyarestudying.Thethirddomainistechnologicalapproachessuchasclickers

andlecturecapturethatallowstudentstoengagemoreinanactivelearningclassroom.Thefourth

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andfinaldomainconsidersthedisciplinethatactivelearningisbeingusedwithin.Thisisimportant,

yetoftenunderrepresenteddomainwithintheactivelearningliterature.

1.1Howimportantisthediscipline-specificpedagogydomain?

Heron showed that active learning which did not address student misconceptions showed no

improvement,howeverthosedidwereparticularyeffective(OritzandHeron,2005;CloseandHeron,

2013).Byapplyingdiscipline-specificconsiderationsHeronwasabletosuccessfullyuseactivelearning

toimprovestudentunderstanding.

Figure2:Studentsmisconceptionsaboutthebalancingobjectsremainedaftercertaintypesofactive

learning.Onlybyunderstanding theoriginsof themisconceptions could successful active learning

tasksbedeveloped(OritzandHeron,2005).

Wereasonthatthosewhowishtouseactivelearningintheirteachingneedtoconsiderdiscipline-

specificpedagogyalongsidetheotherdomainsforittobesuccessful.If,likeintheauthor’sownfield

(organicchemistry),there is littleexisting literatureofstudentmisconceptions,thresholdconcepts

andotherdifficultieswithinthediscipline,designingactivelearningtaskwouldbechallenging.


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2.Projectaims2.1Activelearningtemplate

Anactivelearningtemplatehasbeendesignedthatpractitionerscouldusetodevelopactivelearning

taskswhichwillimprovestudents’conceptualunderstanding.Thetemplateisalsodesignedsothatit

couldbeappliedinanysubject(Figure3).

Figure3:Activelearningtemplatetoimproveconceptualunderstanding

Diagnose –The first stageof theprocess is todiagnosestudent learningwithin thedisciplineand

identify student difficulties. This provides the foundation uponwhich the practitioner can design

activelearningtasks.Tomeetthisgoalanovelmethodfordiagnosingstudentlearningisneededthat

isbothreliablebutalsobeeasytoimplementandanalyse.

Design–Thesecondstageisthedesignofactivelearningmethodsthatwilltargetspecificlearning

difficulties.Herethepractitionermaywanttoconsideranappropriatetheoreticalframeworkinthe

design. For example, the conceptual change model (Duit and Treagust, 2003) stipulates that for

students to learn a concept theymust be dissatisfiedwith oldways of thinking; the newway of

thinkingmustbeintelligible;andthenewwayofthinkingmustbefruitfultolearn.Theactivelearning

taskshouldbedesignedtofollowthetheoreticalframeworkforittobeeffective.

Deliver–Thethirdstageistoincorporatethedesignedactivitiesintoteaching.Byconsideringstudent

difficultiesanddesigningactivelearningaroundthem,theuseofactivelearningwillbemoreeffective.

Evaluationoftheactivelearningtaskcanbeachievedbyrepeatingthediagnostictestwiththegroups

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thathavecompletedtheactivelearningtaskagainsttheearliercohortswhoareusedasthecontrol

group.

2.2Aims

ProjectAim1–Designatemplateforusingactivelearningthatcouldbeappliedacrossdisciplines.

The first aim was to develop and refine the template, and showcase its effectiveness (proof of

concept).Thiswouldbeachievedthroughitsapplicationtowardsaspecificdiscipline.

ProjectAim2–Applythetemplatetowardstwotopicsinchemistryeducation.

There is little research in the area of conceptual understanding in tertiary chemistry education,

particularlyinaUKhighereducation.Thisprovidesanappropriatesubjecttoapplythetemplatewhilst

alsogainingabetterunderstandingastowhystudentsfindtopicswithinthisdisciplinedifficult.

Thefirstchemistrytopicisfundamentalreactivityinorganicchemistry.Thisisatopicwherestudents

apply fundamental concepts of how carbon-based molecules reacts. In many chemistry degree

programmes,theseconceptsaretaughtinthefirstyear.Fortheremainderofthisreportthistopic

withbereferredtoasReactivity.

Figure4:ExampleoforganicmoleculesreactingwhichformspartoftheReactivitytopic

The second topic is stereochemistry in organic chemistry. This is a topic where students learn

propertiesofmoleculesthatarisefromtheir3Dshapes.Fortheremainderofthisreportthistopicwill

bereferredtoMolecularShape.


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Figure5:ExampleofanorganicmoleculeinthreedimensionswhichstudentslearnfortheMolecular

Shapetopic.

Theremainderofthereportwilldiscusstheworkcarriedouttoachievethesetwoaims.Thenext

sectionwill discuss themethodology thatwasdeveloped todiagnose student understanding. The

following sectionswill discuss the active learning templates applied to the two topics in separate

chapters.

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3.Methodology3.1MethodstomeasureconceptualunderstandingForthistemplatetobepractitioner-friendly,amethodofdiagnosingstudentunderstandingofatopic

wasneededwhichwouldprovideanoverviewofstudentunderstandingfromacohortandcouldalso

beeasilyimplemented.Avarietyofexistingmethodshavebeenusedinchemistryeducationresearch.

ThestrengthsandlimitationsofeachmethodsissummarisedinTable1.Noneoftheexistingmethods

satisfied all the requirements that was needed for this project so a bespoke methodology for

diagnosingconceptualunderstandingwasdeveloped(Bretz,2014).

Method Advantages DisadvantagesInterviews(e.g.Bhattacharyya,2014)

Providesdepthofconceptualunderstanding.Showslinkingofmultipleconcepts.

Smallsamplesizeandtime-consumingtoperform.

ConceptInventories(e.g.Mulford2002)

Validatedinstrumentsformeasuringconceptualunderstanding.

Unavailableformanytopics.Cantakeyearstodevelopandvalidateaconceptinventory.Studentsmustcompleteallitemsforvalidity(time-consuming).Mayonlymeasuresingleconcepts.

Analysisofexaminationquestions(e.g.BodéandFlynn,2015)

Largesamplesize. Unabletodistinguishconceptualunderstandingandalgorithmiclearningduetohighstakesassessment.Issueswithobtainingethicalapproval.

Conceptmapping(e.g.AnvovinoandBretz,2016)

Providesdepthofconceptualunderstanding.Showslinkingofmultipleconcepts.

Impracticalduetoamountoftimerequiredforcompletion.

Table1:Summaryofmethodsusedtodiagnosestudentlearninginchemistryeducation.

Themethodologywedevelopedforuseinthistemplatehassomeoftheadvantageswhicharegained

fromusingquantitativemethods (e.g. large scale sampling)blendedwith someof theadvantages

gainedfromofqualitativemethods(e.g.richdepthofdata).

Diagnostic tests were used to gain large scale data which could be analysed using quantitative

methods. The answers of the test were free form so that students could provide explanations

alongsidestructuresandreactionmechanisms.Thiswouldallowstudentstogiverichdata intheir


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answers, showing how they understand multiple concepts in unison which allowing qualitative

methodsofanalysiscouldbeemployed.

3.2DesignanddeliveryofdiagnostictestsAdiagnostictestwasdevelopedforeachtopicwitheachtestcontaining6items.FortheReactivity

teststudentsquestionswerestructuredsotheyhadtoapplymultipleconceptswhenexplaininghow

organicmoleculesreact(summarisedinAppendixA).FortheMolecularshapetopic,eachquestion

wasstructuredsostudentshadtotransferbetween2dimensionaland3dimensionalrepresentations

oforganicmolecules,(summarisedinAppendixA).

Each testwasdelivered to cohortsof studentswhohadbeen taught thematerial previously, and

wouldberequiredtoapplythismaterialinacoursetheywerecurrentlystudying.Thisallowedtous

toalsousethetestsateachingtoolandencourageparticipation.Feedbackwasgiventotheentire

cohortandtoindividualswhochosetogivetheirpersonaldetails.

Figure6:Summaryofhowthediagnosticstestsweredelivered.

Testswerealsodeliveredduringperiodsoftheacademicyearwhenstudentswouldnotbepreparing

for upcoming examinations. Thiswas to reduce the possibility of responses driven by algorithmic

learning rather than conceptual understanding. Each student was randomly assigned one of the

diagnostictestquestionstocompleteandgiven10minutestocomplete.

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DiagnosticTest

Cohort Date Course Numberofresponses

Responsesperitem

Reactivity

Year2Leeds Autumn2016 Compulsory 133 17-26Year2Leeds Autumn2017 Compulsory 106 16-19Year4Warwick Autumn2017 Optional 26 4-5

Total 265 37-50

MolecularShape

Year2Leeds Spring2016 Compulsory 55 7-12Year4Leeds Spring2016 Optional 34 4-7Year4Leeds Spring2018 Optional 38 5-7Year4Warwick Autumn2017 Optional 22 4-5

Total 149 20-31

Table2:NumberofresponsesforbothReactivityandMolecularShapediagnostictests.

Overallweresatisfiedthatthisapproachsatisfiedourrequirementstodevelopamethodofmeasuring

conceptualunderstandinginawaythatwas‘lighttouch’initsapproachandalsoprovidedthescale

anddepthofinformationrequired.

3.3MethodforanalysingdiagnostictestsThemethod for analysing the responseswere developed using thematic analysis as a framework

(BraunandClarke,2006).Ablendquantitativeandqualitativeapproacheswastakentoanalysethe

data to reflect thebalanceof outcomeswewanted to achieve.Qualitativemethods revealed the

complexnatureofconceptualunderstandingwhilstquantitativemethodsallowsustointerpretthe

scaleandsignificanceofconceptualunderstandingacrossacohort,degreeprogrammeorevenacross

institutions(seeAppendixBforanexample).Ouranalysiscanbedividedintoanumberofstages.

3.3.1.InterpretationTo ensure validity in our interpretation of student results, each response was transcribed

independently by two of the researchers. Each transcription was compared with one another.

Agreementbetweenthetwotranscriptionssignifiesavalidinterpretationofthestudentanswerand

thosewithoutagreementpromptedfurtherdiscussion.

Before discussion the agreement across all answers was 84%. This rose to 95% after discussion

revealedthemajorityofdifferencesweresimplydifferingwordingsofthesameinterpretation.For

theremaining5%therewasnoagreementsotheseinterpretationswerenottakenforward.


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3.3.2.Codingandscoring

Codesweregeneratedforeachdiagnostictestquestionwhichcorrespondedtoaparticularconcept

or aspect of answering the question. These were generated in an implicit manner using student

responses.Eachconceptwasgivenascoreof+/-1.

3.3.3.RankingandclusteringStudentresponseswererankedbyscore.Asexpectedstudentswithhigherscorescorrectlyapplied

more concepts than thosewith lower scores. The value of this quantitative approachwas that it

revealedclustersofstudentswhowerecorrectlyorincorrectlyapplyingcertainconcepts.

3.3.4.ClusteranalysisTheresponsesineachclusterwereanalysedagainbutnowinterpretedinaqualitativemanner.Within

eachclusterthemeswereidentifiedbytheresearchers,i.e.studentsineachclusterwererevealing

thesameconceptualunderstanding.

3.3.5.Cross-sectionalanalysisFinally clusters and themeswere compared across questions. Comparing clusters across different

questions revealed similar responses in each question. As with the previous step this helped to

developoverarchingthemesinouranalysis.

3.4ValidationofthemethodologyWerecentlyconductedstudentinterviewsofthediagnosticquestionstovalidateourinterpretations.

Pleasingly,whenstudentsdiscussedtheirthoughtprocessestheymatchedourinterpretationsofthe

test results. Overall method that we developed validated its purpose for identifying conceptual

understandingacrossalargenumberofstudents.Whenconsideringthatclustersofstudentswere

givingthesameresponsesacrossdifferentyeargroupsthenitislikelythatsimilarlevelsofconceptual

understandingormisconceptionsarebeingapplied.Thefindingsfromeachtopicanditsapplication

towardstherestofthestrategywillbediscussedinthefollowingsections.

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4.Reactivitytopic|resultsanddiscussion4.1OrganicchemistryOrganicchemistryisatopicthatistraditionallyseentobehardtolearn(Graulich,2015).Amongstthe

difficulties encounter, one is the requirement to usemultiple conceptswhen solvingmechanistic

problems(CartretteandBodner,2010).Tothenoviceitcanalsoappearthatthemasteryisachieved

bylearninglotsof information,howevertherealityisthatafewunderlyingconceptsunderpinthe

majorityofchemicalreactions.Novicestendtousesurfacefeaturestomakeconnectionsbetween

structure and reactivity whilst experts use these concepts to make deep underlying connections

(GallowayandFlynn,2018).Itisimportantforstudentstounderstandandapplythematerialinthe

samewayasexpertsasitthiswillleadtoimprovedperformanceinthesubject(Frey,2017).

4.2ResultsfromtheReactivitydiagnostictestsClusteringofresultsduringthequantitativeanalysisallowedresponsestobeclassifiedinto3general

groups(AppendixCforadetailedbreakdown).

1. Correctanswers:Aanswerwhereallormostoftheconceptswerecorrectlyused.

2. Partiallycorrectanswers:Thesefollowedthepatternwheresomeconceptswerecorrectly

usedbutotherswereincorrectornotusedatall.

3. Incorrect answers: The initial concepts needed were used incorrectly and the following

conceptswerenotused.

Student fromLeedswhocompletedthetests inautumn2016and2017showedsimilarresults for

questions1-4ofthediagnostictest,whethertheiranswerswerecorrect,partiallycorrectorincorrect.

Thissuggeststhatstudentshavespecificlevelsofunderstandingthatisindependenttotheteaching

theyhavereceivedinyear.

Initialanalysisofquestion5and6fromthe2016cohortconcludedthatthestructureandwordingof

thequestionsweretooambiguousforstudents,hencetheirresultswerenotanalysedfurther.These

questionsweremodifiedforthe2017cohort.

Question1andquestion3oftheReactivitytestaskedstudentstoapplytheirunderstandingtothe

sametypeofchemicalreactionandsotheyproducedthesametypeofcorrect,partiallycorrectand


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incorrectanswers.Inalltypesofanswerstudentswouldapplyelectronegativity,aconceptintroduced

insecondaryeducation,toanswerthequestion.Thisconceptprovidesapartiallycorrectanswerif

correctlyused,howeverbutsomestudentsusedtheconcept incorrectly.FMOtheory isaconcept

introduced in tertiary education that could have also been applied instead of electronegativity

(secondaryconcept)togetthefirstpartoftheanswercorrectbutthiswasnotusedbyanygroupof

students. Partially correct students only applied electronegativity (secondary concept) whereas

studentswhoachievedthefullycorrectansweralsoappliedeitheracid-basetheory(tertiaryconcept)

orresonance(tertiaryconcept).

Question2wasgenerallywellanswered.Herestudentscouldusejustoneconcepttogetthecorrect

answer instead of having to apply a number of different concepts, hence the question could be

deemed to be easier. Some students gave partially correct answers by providing the correct

mechanismsbutforthewrongcompounds.Itwasthoughtthatthesewereanswersduememorisation

oftheanswersbutnoconceptualunderstandingtoapplytothecorrectchemicalreaction.

Question4gaveaverysimilarpatternof results toquestions1and3.Almostall studentsapplied

electronegativity (secondary concept) correctly to answer the first part of the chemical reaction.

However,toachievethefullycorrectanswertertiaryconceptswereneededinthesecondpartofthe

chemicalreaction.Heremoststudentsfailedtoapplythetertiaryconceptsleavingtheirresponsesas

partiallycorrect.Infact,thepartiallycorrectchemicalreactionsareexactlywhatistaughtinsecondary

educationandwouldbefullycorrectatthatlevel.

Acrosstheanswerstothesefourquestionsageneralthemebegantoemergewherebystudentswere

consistentlyapplyingtheconceptstaughttotheminsecondaryeducation.A lackofapplicationof

tertiaryconceptsledtoourconclusionthatstudentshadapoorunderstandingoftheseconcepts.We

alsoreasonedthatthiswaslinkedtotheirrelianceonconceptstaughtatthesecondarylevel.

4.3DesigningactivelearningworkshopsfortertiarylevelconceptsInthemajorityofanswersstudentswerereliantonsecondaryconceptstounderstandfundamental

organicreactionswhethertheyarecorrect,incorrectorpartiallycorrectresponses.Thereasonmore

complicatedconceptsareintroducedinhighereducationisthatthesesimplerconceptsbreakdown

andsohigherlevelsofunderstandingareneeded.Thestrategyofbreakingdownsimplermodelsto

introducemorecomplicatedmodels iscommonpractice indevelopingconceptsscienceeducation

andonethatstudentswillhaveencounteredthroughouttheirstudies.

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Tohelpstudentsunderstandthetertiarylevelconceptswedecidedtoapplytheconceptualchange

framework(DuitandTreagust,2003)appliesthemodelorbreakingdownoldconceptstolearnnew

ones. The framework states that for students to change or adapt their conceptual thinking, new

conceptsmustbeintroducedthroughthefollowingsteps:

1. Becomedissatisfiedwiththeoldwaysofthinking

2. Presentnewconceptsinanintelligibleway

3. Appearfruitfultolearnnewconcepts

Active learning tasks were developed in the form of problem-based learning workshops where

studentswouldgiveninformationandstructuredquestionsrelatingtovariousconcepts.Becausethe

understandingoftertiaryconceptswaslinkedtosecondaryconcepts,thefirstpartoftheworkshop

wouldfocusonexposingthe limitationsof thesecondaryconcepts (conceptualchangeframework

step1)with specificquestions. Tertiary conceptswould thenbe introduced (step2) and students

wouldworkthroughquestionsthatcouldonlybeansweredusingthetertiaryconcepts(step3).

4.4DeliveringactivelearningworkshopsfortertiarylevelconceptsManyof these concepts are first introduced in CHEM1000 ‘An introduction tomodern chemistry’

whichrunsasa20creditmoduleinsemester1.Forthedurationofthismodule,1hourworkshops

aredeliveredonaweeklybasistocomplementthelectures.Theorganicchemistrylecturesaretaught

byProfessorPaulTaylorwhoafterdiscussionofdiagnostictestresultsagreedtousetwoofthese

workshopsforouractivelearningtasks.

The first workshop was themed around the structure of the carbonyl functional group. In this

workshopstudentswoulduseelectronegativity(secondaryconcept),FMOtheory(tertiaryconcept)

and resonance (tertiary concept) to solve problems with the emphasis on why FMO theory and

resonanceisneededtohaveafullunderstandingofstructure.

Thesecondworkshopwasthemedaroundatypeofreactivityexhibitedbythecarbonylfunctional

group.Theimportanceofresonance(tertiaryconcept)wasreinforcedwhilstacid-basetheory(tertiary

concept) was also introduced. Again, the workshop highlighted why electronegativity (secondary

concept)onlygivespartialunderstandingofitsreactivity.


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4.5DeterminingthesuccessoftheactivelearningworkshopsThese students completed theirCHEM1000examination in January. Their results relating to these

conceptswillbeanalysed.Thestudentswillalsocompletethesamediagnostictestsarethe2016and

2017cohortsinautumn2018.Theirresultswillbecomparedtothe2016/17cohortswhowillactasa

controlgroup.

4.6SummaryoftheactivelearningstrategyappliedtoReactivityTosummarise,wehaveappliedthestrategytothetopicofReactivityinorganicchemistry.Ourkey

findings from thediagnostic testswere that students reliedon concepts learnt in their secondary

education to understand the reactivity of organic molecules to mixed success. To help them

understand concepts taught in tertiary chemistry education, which would ensure improved

understandingofthereactivityoforganicmolecules,weappliedtheconceptualchangeframeworkto

designworkshopsthatexposethelimitationsofusingthesesimplermodels.Theseweredeliveredin

themoduleCHEM1000whichintroducesthesestudentstotheseconcepts.

Weareinterestingininvestigatingifthisthemeofusingsecondary-levelconceptsisalsoappliedin

otherUKhighereducationchemistrydepartments,andifthislinkstopoorunderstandingoftertiary

conceptsasshownwithstudentsfromtheUniversityofLeeds.WehavepartneredwiththeUniversity

ofWarwickandUniversityofYorktoanalysetheirstudents’responses.Todatewehavedatafroma

cohort ofWarwick students withmore data from both institutions to be received in the coming

months. If there is a similarpatternemerging then it shedsnew lightofhowwe teach chemistry

conceptsacrosssecondaryandtertiary levelwith implicationsofhowwedesignthecurriculumat

bothlevels.

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5.Molecularshapetopic|resultsanddiscussion5.1MolecularShape(stereochemistry)Molecularshape(orstereochemistryasit’stechnicallyknown)requiresstudentstounderstandthe

propertiesofmoleculesusing3D-spatialreasoning.Oneofthemostdifficulttasksforstudentstodo

istranslatebetweentheserepresentations(VlacholiaM,2017).Whenstudentsaregiveninstruction

ofusing3Dmodelsofmolecules,eitherinaphysicalorcomputationalform,theirperformanceon

Molecular Shape improves (Stull 2016). Other attempts to improve performance encourages

algorithmicapproachesthatbypass3Dspatialthinking(Hutchinson,2017).

Figure7: Studentsmustbeable to translatebetween2Dand3D representationsofmolecules to

understandtheirproperties.

5.2ResultsfromMolecularShapediagnostictestsTestsformolecularshapewerecompletedbytwocohortsofLeedsstudentsindifferentyeargroups

butwhobothreceivedinstructionfromtheauthoronthistopic.Warwickstudentsalsocompleted

thediagnostictests.

Allgroupsofstudentsgaveasimilarpatternofresults.Veryfewstudentsgaveanswersthatwere

completely incorrect. Rather the main differences in answers lay in subtleties which determined

whether the answers were fully correct or partially correct. Nevertheless, these partially correct

resultsrevealedacommonpatternwhichwecoulddetermineaswehadtaughttheLeedsstudents

this topic. Students were given a particular style of instruction of how to translate between

representationsusingexemplarmolecules.Itwasexpectedthatstudentswouldlearnhowtotranslate

betweenrepresentationsusingtheseexampleswhilstalsothinkingabout3Dshapeofthemolecule

sothattheinstructionscouldbeadaptedwhenaskedtoviewmoleculesfromdifferentperspectives.

However,becausethesestudentswerelearningthetranslationsbyroteandwithout3Dthinking,their

answerscontainedconsistentmistakes.


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Manyoftheerrorsfellintoafewcategories:

1. Viewingthemoleculealongthewrongdirectionofthebond.

2. Drawingfunctionalgroupsonthewrongsideofthecentralcarbonatom.

3. Notdrawingbondsfacingforwardsorbackwardswhenneeded.

Whilst thedetailsof instructionwasnotaswell-knownwithWarwickstudents, thesesameerrors

persisted, implying that they too were translating between representations without 3D spatial

thinking.

5.3Developingactivelearningresourcesfor3DspatialreasoningAswiththeReactivitytopic,ourstrategyforactivelearningistohelpstudentsseethelimitationsof

usingtheirexistingapproachestolearnthecorrectapproachwayofthinking.Inthiscasethestrategy

wastoimprovestudents’abilitytotranslatebetweenrepresentationsbyteachingthemhowtouse

3Dmodelsandbyextensionhowtothinkin3D.Molecularmodelscanbeeitherbeintheformof

physical model kits, or computer-based models. Whilst physical models are sometimes given to

students,itisrarethattheybringthesetolecturessousingphysicalmodelswouldbeanunreliable

method. Online resources such as ChemTube3D (www.chemtube3D.com) are available to allow

studentstoviewmoleculesin3Dbuttheycontainlittletonoinstructionofhowstudentsshoulduse

themtotranslatebetweentworepresentations.

5.4Creatingafreeonlinetooltotranslatebetween2Dand3DrepresentationsTobeabletouseactivelearningtoimprove3-dimensionalspatialthinkingitbecameapparentthat

weneededtocreatearesourcethatwouldguidestudentsbetweenrepresentationswitha3Dmodel.

Wedecidedtousecomputationalmodelsasafreeonlineresourceasthiswouldgivemaximumaccess

to students.We are currently workingwith the Technology Enhanced Learning team inMAPS to

achieve this. Once the resource has been created active learning workshops will be created for

studentstoengagewiththeresource.

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5.5CreatingatextbooktoteachMolecularShapeA tutorial textbook has been commissioned by the Royal Society of Chemistry on the topic of

molecularshape,writtenbytheauthorwiththeProfessorPaulTaylorattheUniversityLeeds,and

ProfessorAndrewClarkeandDrRussellKitsonattheUniversityofWarwick.

The textbookwill focus on the problems students facewith 3D representation ofmolecules. The

resultsfromthediagnostictestshavebeenveryusefulinhighlightingtheissuesstudentsfaceandwill

guidethestructureofthebookandtheproblemsforstudentstoworkthrough.Theonlineresources

beingcreatedwillbeusedasaresourcetosupplementthebookaswell.


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6.ConclusionsOverallwehaveachievedthemainaimofthisprojecttopilottheactivelearningtemplateandprove

thatitcanbeusedtoidentifymisconceptionswhichcanbeusedtodevelopactivelearningmethods.

Thetemplatehasbeenrefinedbaseduponourexperienceofapplying it inpractice.Thetemplate

usesanovelmethod fordeterminingmisconceptionsand thresholdconcepts from theanalysisof

diagnostictests.Overarchingthemesofhowstudentsunderstandconceptsofmolecularshapeand

reactivity were discovered from our analysis from students at Leeds, and we are beginning to

investigateifthesefindingsarereplicatedatotheruniversitiestogainanationalpicture.Preliminary

analysisofstudentsattheUniversityofWarwickrevealthattherearesimilaritieswithLeedsstudents

wheninterpretingmolecularshape.

Forthereactivitytopicwediscoveredwasthatstudentsrelyalmostexclusivelyonconceptslearntin

secondaryeducationwhetherthatistoachievethecorrect,partiallycorrectorincorrectanswer.We

hypothesisedthattherelianceonthesesimplermodelstostudentshavingapoorunderstandingof

theconceptstaughtintertiaryeducation.Activelearningworkshopsweredesignedforthemodule

CHEM1000whichusedtheconceptualchangeframework.Thestrategywastohelpstudentsseethe

limitationsofthesesecondaryconceptstothenvalueofthenewconceptintroduced.

Forthemolecularshapetopicwediscoveredthatstudents learnttotranslatebetween2Dand3D

representationsofmoleculesbyalgorithmicmethodswhichmeant incorrect representationswere

produced when looking from different perspectives. Resources are being created that will help

studentsuse3-dimensionalstructuresofmoleculesasawayoftranslatingbetweenrepresentations

intheformofanonlineresourceandatextbookpublishedwiththeRoyalSocietyofChemistry.

6.1Futurework

• Wearecontinuingtoinvestigatethewaysstudentslearninthesetwotopicstoseeifstudents

thesearegeneral issueswhichaffectsall chemistry students irrespectiveof the institution

theyarestudying.

• Theimpactofouractivelearningworkshopswillbemeasuredinthecomingyearswhenthe

studentreachthesamepointintheirstudiesaspreviousstudentswhohavecompletedthe

diagnostictests.

• Boththeonline3Dmolecularresourceandtextbookwillbecomeavailableinthecomingyears

tohelpstudentsvisualisemoleculesin3D.

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• Wewilllooktoapplytheactivelearningstrategyinothersubjectareas.

AdetailedtimelineofthecurrentandfutureobjectivesoftheprojectisavailableinAppendixD.Past

andfutureoutputsareavailableinAppendixE.


25

ReferencesAnzovino,M.E.,Bretz,S.L.,2016,Organicchemistrystudents’fragmentedideasaboutthestructureandfunctionofnucleophilesandelectrophiles:aconceptmapanalysis,ChemistryEducationResearchandPractice,17,1019-1029.Bhattacharyya,G.,2014,Trialsandtribulations:studentapproachesanddifficultieswithproposingmechanismsusingtheelectron-pushingformalism,ChemistryEducationResearchandPractice,15,594-609.Bodé,N.E.,Flynn,A.B.,2015,Strategiesofsuccessfulsynthesissolutions:mapping,mechanismsandmore,JournalofChemicalEducation,93,593-604.Braun,V.,Clarke,V.,2006,Usingthematicanalysisinpsychology,QualitativeResearchinPsychology,3,77-101.Bretz S. L., 2014, Designing assessment tools to measure students’ conceptual knowledge ofchemistry,In:ToolsofChemistryEducationResearch,AmericanChemicalSociety,155-168.Cartrette,D.P.,Bodner,G.M.,2010,Non-mathematicalproblemsolvinginorganicchemistry,Journalofresearchinscienceteaching,47,643-660.Close,H.G.,andHeron,P.R.L.,2013,StudentunderstandingoftheapplicationofNewton’ssecondlawtorotatingrigidbodies,AmericanJournalofPhysics,81,458-470.Duit, R., Treagust, D. F., 2003, Conceptual Change: A powerful framework for improving scienceteachingandlearning,InternationalJournalofScienceEducation,25,671-688.Freeman,S.etal,2014,Active learning increasesstudentperformanceinscience,engineeringandmathematics,ProceedingsoftheNationalAcademyofSciences,111,8410-8415.Frey,R.F.,etal,2017,Studentconcept-buildingapproaches:anovelpredictorofsuccessinorganicchemistrycourses,JournalofChemistryEducation,94,1185-1194.Galloway,K.R.,andFlynn,A.B.,2018,[Forthcoming].Acomparisonofhowundergraduates,graduatestudents, and professors organize organic chemistry reactions, Journal of Chemical Education,[Online].[Accessed5March2018].Availablefromhttps://pubs.acs.org/journal/jceda8.Graulich,N.,2015,Thetipoftheiceberginorganicchemistryclasses:howtostudentsdealwiththeinvisible?,ChemistryEducationResearchandPractice,16,9-21.Haak,D.C.,andFreeman,S.,2011,Increasedstructureandactivelearningreducetheachievementgapinintroductorybiology,Science,332,1213-1216.Hutchinson, D. M., 2017, Improving translational accuracy between dash-wedge diagrams andnewmanprojections,JournalofChemicalEducation,94,892-896.Mulford, D. R., and Robinson,W. R., 2002, An inventory for alternative conceptions among first-semestergeneralchemistrystudents,JournalofChemicalEducation,79,739-744.

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Ortiz, L.G., andHeron, P. R. L., 2005, Student understandingof static equilibrium:predicting andaccountingforbalancing,AmericanJournalofPhysics,73,545-553.Stull,A. T.,etal, 2016,Promoting representational competencewithmolecularmodels inorganicchemistry,JournalofChemicalEducation,93,994-1001.VlacholiaM.,2017,Changesinvisual/spatialandanalyticstrategyuseinorganicchemistrywiththedevelopmentofexpertise,ChemistryEducationResearchandPractice,18,763-773.


27

AppendicesAppendixA|SummaryofconceptsusedforbothReactivityandMolecularShapediagnostictests

DiagnosticTest Concept Question1 2 3 4 5 6

Reactivity

Electronegativity X X X X X XStructure(stability) X X X Sterics X Resonance X X XAcid-Basetheory X X FMOtheory X X X X Stereochemistry X

Table3:SummaryofconceptsusedinReactivitydiagnostictest.

DiagnosticTest Concept Question1 2 3 4 5 6

Molecularshape

Enantiomers X X Diastereomers X Sterics X X 2Dto3Drepresentation X X X 3Dto2Drepresentation X X3Dvisualisation X X X X X X

Table4:SummaryofconceptsusedinMolecularShapediagnostictest.

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AppendixB|Exampleoftheanalysismethodology

Figure8:Anexampleoftheanalysismethodologyappliedtoquestion1oftheReactivityconceptquiz.Theleft-handportionshowsthequantitativeanalysisthatwasusedtoclusterstudentresponses.Thegreen (correct)and red (incorrect) segments indicate thecorrector incorrectuseofeachconceptrespectively.Qualitativeanalysisshowedresponsesineachclusterwerethesame,implyingstudentshadthesamelevelofunderstandingwithineachcluster.


29

AppendixC|ResultsfromReactivitydiagnostictestsResultsfromReactivitydiagnostictestsfromLeeds2016studentsshowshowstudentsconsistentlyapplyconceptslearntinsecondaryeducation,whilstthosetaughtintertiaryeducationwererarelyused.

Concept Introduced in secondaryortertiaryeducation

Question

1 2 3 4 5 6Electronegativity Secondary X X X X X XStructure(stability) Secondary X X X Sterics Secondary X Resonance Tertiary X X XAcid-Basetheory Tertiary X X FMOtheory Tertiary X X X X Stereochemistry Tertiary X

Table5:Breakdownofconceptsineachquestionandwhethertheyaretaughtinsecondaryortertiaryeducation.Question1(N=42)Responses Correct Partiallycorrect IncorrectQuestion1(N=42) 13

31%717%

2252%

Electronegativity(secondary) Correctuse Correctuse IncorrectuseAcid-basetheory(tertiary) Correctuse Nouse NouseResonance(tertiary) Incorrectuse Nouse NouseFMOtheory Nouse Nouse Nouse

Question3(N=34)Responses Correct Partiallycorrect IncorrectQuestion3(N=34) 11

33%1441%

927%


Question1and3combined(N=76)Responses Correct Partiallycorrect IncorrectQuestion3(N=34) 24

31%2128%

3141%


AppendixD|TimelineofprojectobjectivesandimpactLocalimpactisinblueExternalimpactisinred


31

AppendixE|SummaryofprojectdisseminationConferencetalks/posters

Date Event Organiser Location Poster/Talk StatusMay17 Methodsin

ChemistryEducationResearch(MICER17)

RoyalSocietyofChemistry

Burlingtonhouse,London

Poster Delivered

Aug17 VarietyinChemistryEducation(VICEPHEC17)

RoyalSocietyofChemistry,InstituteofPhysics

UniversityofYork

Poster Delivered

Jan18 StudentEducationConference

LITE UniversityofLeeds

Talk Delivered

Mar18 WorkinProgressseminar

LITE UniversityofLeeds

Talk Abstractaccepted

Mar18 ChemicalEducationResearchGroupWebinar

RoyalSocietyofChemistry

Online Talk Invitedtalk

May18 SEDAAnnualConference

SEDA Hilton,Leeds Talk Abstractaccepted

Jul18 HEAAnnualConference

HigherEducationAcademy

Birmingham Talk Abstractaccepted

Publications

Date Topic Type StatusSep18 Conceptualunderstandingof

ReactivitytopicofLeedsstudents

JournalArticle TargetjournalsincludeJChemEdandCERP

Dec18 RoyalSocietyofChemistrystereochemistrytextbook

Book TextbookcommissionedbyRSC

Jan19 MolecularShapeunderstandingofLeedsstudents

BookChapter InvitedchaptercontributionforFestschrift

Aug19 ConceptualunderstandingofReactivitytopicatnationalscale


Aug19 MolecularShapeunderstandingatnationalscale


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AbouttheauthorandacknowledgementsAbouttheauthorNimeshisaSeniorTeachingFellowintheSchoolofChemistry.HeiscurrentlyholderofaUniversity

StudentEducationFellowship.

HeobtainedanMCheminMedicinalChemistryattheUniversityofLeedsin2006,whichalsoincluded

a year in industry with GlaxoSmithKline. After his undergraduate degree, Nimesh undertook his

doctorate in the Clarke group at the University of York working towards the synthesis of (+)-

phorboxazoleB,amarinenaturalproductwithpotentanti-cancerproperties.HeremainedinYorkfor

ashortpostdoctoralfellowshipintheClarkeandThomasgroupbeforebeingappointedasaTeaching

FellowintheDepartmentofChemistryin2011.In2013,hemovedbacktotheUniversityofLeedsto

takeuphiscurrentposition.

Hisresearchinterestsareinthedevelopmentofinnovativeapproachestoenhancestudenteducation

usingthescholarshipandpedagogicresearch.Mostofhisworksofarhasbeenwithinthecontextof

chemistryeducationbutcanbeappliedintomanyotherdisciplines.

Acknowledgements

IwouldlikeeverybodyattheLITEteamforsupportingthisprojectandprovidinghelpandguidance

throughout. Iwouldalso like to thankSteveMarsdenandPaulTaylor for their supportwithin the

SchoolofChemistry.IamgratefultoRussKitsonattheUniversityofWarwickandGlennHurstatthe

UniversityofYorkforkindlyagreeingtousethediagnostictestsattheirrespectiveinstitutions.Iwould

liketothankSamanthaPughforsupportingtheethicalapprovalforprojectthroughPRISM.Finally,I

wouldliketothankMichaelLloydandStevenNicholsonfortheirexcellentcontributionstowardsthis

work.

[email protected]

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A STRATEGY TO ENHANCE CONCEPTUAL ......Project Aim 1 – Design a template for using active learning that could be applied across disciplines. The first aim was to develop and refine

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