Chemistry251(OrganicChemistryLectureI)

SYLLABUS

Fall2008(rev09.02.08)

Prof.MariettaSchwartz
Office:S1082
Telephone:617.287.6146
Email:marietta.schwartz@umb.edu

CourseWebPage:http://www.chem.umb.edu/chemistry/orgchem/

ThiscoursesatisfiestheNaturalSciencesDistributionRequirement.Itofferstheopportunitytocontinue
exploringthelawsofthephysicalandbiologicalworld,howtheyarederivedandtestedthroughobservation,
theory,andexperiment,andprovidesanunderstandingoftheAcorrectable@natureofscientificknowledge
andtheinterconnectionsamongscience,technology,andsocialconcerns.Inclassinstructionandpracticeis
providedinQuantitativeReasoningandtheUseofTechnologytoFurtherLearning.
PLEASENOTE:YOUMUSTALSOBEENROLLEDINCH255,ORGANICLABORATORYI!!
BasicCourseInformation
Lecture:
MWF 11:00AMC12:00Noon(ScienceBuilding,LipkeAuditorium)
Discussion: M(1:00PM),T(2:00PM),W(1:00PM),Th(2:00PM),F(1:00PM)allinS2062.

RequiredMaterials: AOrganicChemistry@,Solomons&Fryhle,9thedition(asolutionmanual/studyguideisalso
available)

AniClickerisrequired.ThesecanbepurchasedonlyattheUMBbookstore.Thislookslikea
smallTVremotecontrol.YoutransmityouranswertothereceiverinLipkeand
youranswerisloggedbythecomputer.(SameastheoneusedinBiologycourses;if
youalreadyhaveoneofthose,itwillworkinthisclassalso.)

CourseContent:Chapters110.

Exams:
Therewillbefour(4)inclassexamsandafinal,tobegivenonthedateslistedbelow.
Wednesday,October1
Friday,October31
Friday,November21
Friday,December12
(FinalexamasscheduledbytheRegistrarsOfficetheweekofDecember1519.)
SupplementaryMaterials
APushingElectrons,AGuideforStudentsofOrganicChemistry@,D.P.Weeks,3rdedition,andOrganicChemistryasa
SecondLanguage,DavidKlein(note:thefirsteditionwasonebook;thesecondeditionhasbeensplitintotwo
books,oneforeachsemester.Eitherversionisfine;thisresourceishighlyrecommended.Infact,itshouldcome

Marietta Schwartz, Ph.D 2008

ocw.umb.edu

bundledwiththetextbook.)ChemOfficesoftwareisavailableonthecomputerlabsinthelibrary(youdontneedto
purchaseit).
GeneralInformation
Thiscourseconsistsoflectureanddiscussion.AsofFall2008,theorganiclaboratoryisaseparatecourse(CH255and
CH256,OrganicLaboratoryI/II).Therewillbenolabcreditallowedforstudentswhotookthelabintheprevious
versionofthecourse(CH253);CH251andCH255arecorequisites,andstudentsmustbeenrolledinandattending
bothcourses.
ThereareNOMAKEUPEXAMS.Thelowestscorefromthefirstthreeinclassexamswillbedropped.
Incompletesforthiscourseareonlyallowedunderexceptionalcircumstances,andarenevergrantedautomatically.
Thismeansthatifyouthinkyouqualifyforanincomplete,youmustrequestone!ThebasicrequirementsforanINC
are:(1)youmustbepassingthecourse,and(2)youmusthaveaninsurmountablereasonfornotbeingabletofinish
thecourse.INCsarenevergivenbeforethewithdrawaldeadlinehaspassed.
Accommodations:Section504oftheAmericanswithDisabilitiesActof1990offersguidelinesforcurriculum
modificationsandadaptationsforstudentswithdocumenteddisabilities.Ifapplicable,studentsmayobtain
adaptationrecommendationsfromtheRossCenterforDisabilityServices,M1401,(6172877430).Thestudent
mustpresenttheserecommendationsanddiscussthemwitheachprofessorwithinareasonableperiod,preferably
bytheendoftheDrop/Addperiod.
StudentConduct:StudentsarerequiredtoadheretotheUniversityPolicyonAcademicStandardsandCheating,to
theUniversityStatementonPlagiarismandtheDocumentationofWrittenWork,andtotheCodeofStudentConduct
asdelineatedintheUniversityCatalogandStudentHandbook.TheCodeisavailableonlineat:
http://www.umb.edu/student_services/student_rights/code_conduct.html.
ExtraCredit
OWL.Youmayaddupto30points(3%)toyourtotalscorebyworkingontheOWL(OnlineWebbasedLearning)

system.Thisisanonlinehomeworksystemthatallowsmultipletriesatquestions,withthequestionschanging
randomly.Thesystemcanbeaccessedathttp://owl.oit.umass.eduandmoreinformation(andalinktothesite)
isavailableonthecoursewebsite.Pleasebesuretochecktheduedatesforthevarioussections.Notethatthe
assignmentnumbersonOWLdoNOTcorrelatewiththechapternumbersinthetextbook.Lookatthetopics
insteadofthenumbers.
iClickers.YouarerequiredtopurchaseaniClickerremoteforinclassparticipation.iClickerisaresponsesystem

thatallowsyoutorespondtoquestionsIposeduringclass,andyoucanaddupto20points(2%)toyourtotal
scorebyparticipating.Inordertoreceivethiscredit,youwillneedtoregisteryouriClickerremoteonlinewithin
thefirstweekofclass.Youmusthavecometoclassatleastonceandvotedonatleastonequestioninorderto
completethisregistrationproperly.Onceyouhavevotedonaquestioninmyclass,goto
http://www.iclicker.com/registration.Completethefieldswithyourfirstname,lastname,studentID,and
remoteID.YourstudentIDshouldbetheeightdigitsofyourUMSnumber.TheremoteIDistheseriesof
numbersandsometimeslettersfoundonthebottomofthebackofyouriClickerremote.iClickerwillbeused
mostdaysinclass,andyouareresponsibleforbringingyourremotedaily.

Discussion/POGIL.Thisyear,wewillbedoingregularactivitiesindiscussion,calledPOGIL(processoriented

guidedinquirylearning;http://www.pogil.orgformoreinformation).Youcanaddupto20points(2%)toyour
totalscorebyparticipating.Thereisaworkbookforthis;itwillbeavailableinthebookstore(alongwithastudent
solutionmanual).Thefirstfewactivitiesarepostedonawebsitesincethepublisherranoutofbooks!Goto
http://www.pogil.org/workbook2e/forthematerials.
HomeworkAssignments
Alistofselectedproblemsfromtheendofeachchapterisavailableonthecoursewebpage.Theseproblemsshould
bedoneataminimum.Youareencouragedtodoasmanyoftheproblems,bothwithinthechapterandattheendof
thechapter,aspossible.Organicchemistryislearnedbydoing,notbyreading;thereforeitistoyouradvantagetodo
asmanyproblemsaspossible.Seethecoursewebpageforlinkstoonlinesourcesofproblemsaswell.
MiscellaneousInformation

Ausefulpieceofequipmentforthecourseisamolecularmodelingkit(availableatthebookstore).Many
aspectsoforganicchemistryareeasiertounderstandwhenmodelsareusedasastudyaid.Bothmodelsand
calculatorsmaybeusedduringexamsifdesired.

TutorsareavailablethroughAcademicSupportServices(CampusCenter,1stFloor)

LearningOrganicChemistry
Learningorganicchemistryisnoteasy;itrequiresyoutocommitbothtimeandintellectualeffort.Learninganything
requiresreinforcementthroughrepetition,especiallyindifferentcontexts.
Lectures:

Notes:

Textbook:

Homework: 1

Laboratory:

learnwithyourears
rankimportanceoftopics(chaptersummarieshelp)
focusyourattentiononthesubject
shouldberewrittenafterclasslearnbywriting
notjustforreading,butreadwithconcentrationandthought
veryimportant!helpfulforyoudoyouKNOWthematerial?
workingroupsifyoucanexplainit,youprobablyknowit
doNOTusetheanswerbookuntilafteryouattempttheproblems!
experimentaltechniquesoforganicchemistry
reinforcementtolearningthelecturematerial
NOTtwodifferentsubjects!trytorelatetolectureatalltimes

1.Some problems are routine drill, while others are more challenging and require you to sort
out the concepts and patterns relevant to the problem and then apply them in a logical way to the
development of an answer. You will learn organic chemistry best by doing the problems!

GeneralIntroduction
or
WHOSEBRILLIANTIDEAWASITFORMETOTAKEORGANICCHEMISTRY,ANYWAY? 2

Goodquestion.Whatistheproblemwithorganicchemistrythatcausessomanystudentstoviewtheclasswithso
muchanxiety?Ithinkthereareatleasttwogoodreasons:
1. Verybadexperiencesinfreshmanchemistry.Evenstudentsinterestedinchemistryfindsignificantstretches
of"ChemI"tobeintolerablydull.
2. Commentsfromstudentswho'vejustfinishedtakingorganicchemistry.Forexample:"youhavetomemorize
eighthundredmillionreactions,andthentheydon'tevenaskyoutheonesyou'vehadinclassonthetests."
Let'staketheseoneatatime.Freshmanchemistryisalittlelikescrambledeggswithalotofotheringredientsmixed
in:alittlebitoftheoreticalchemistry(electronicstructure,bonding),physicalchemistry(gaslaws,equilibria,
kinetics),inorganicchemistry(periodictable,descriptivechemistryoftheelements,coordinationcompounds),
organicchemistry(hydrocarbons,othertypesofcarboncompounds),andwhoknowswhatelse.Nowondersomany
studentsfinishthefirstyearofchemistrywithouttheslightesttraceofanoverviewofwhatthey'vesatthrough,or
thefaintesthintofanideaofwhat'ssupposedtocomenext.Theproblemisthat"chemistry"isaverybigoperation
thatcoversalotofterritory.Itstartswithatoms,butcangoinlotsofdirections,andeachofthesecangetpretty
complicated.Fornow,allyouneedtoknowisthatonlyaportionofwhatyousawinfreshmanchemistryisnecessary
asbackgroundfororganicchemistry.Thiswillbethesubjectofthefirstchapterofyourtextbook.
Asforthesecondreasonpeopleareafraidoforganicchemistry,allthatfamous"memorizing"youhavetodo,like
moststoriesheardoverandoveragain,thereistruthtoit.Youwillhavetomemorizealotoforganicchemistry.
However,youwon'thavetomemorizeeighthundredmillionreactions.Ifyoutrytodothat,youwillbeluckytopass
thecourseevenifyousucceed.Whatyoureallyhavetomemorizearesomebasicpropertiesofatomsandmolecules,
anumberofprinciplesthatdescribewhyandhowreactionstakeplace,andanumberofreactiontypesthatlatercan
begeneralizedtoincludethevariousreactionsoforganiccompoundsthatyouwillseethroughoutthecourse.From
thisframeworkyouwillbeshownhowthevariousdetailsoforganicchemistryarederivedfromsomebasicprinciples
or"groundrules".You'llbeexpectedtolearnabout,andreallyunderstandthesegroundrules,sothatyoucanapply
theminalogicalwaytocompletelynewkindsofsituations,andcomeupwithsensibleanswers.It'salittlelike
learningarithmetic.Youalllearnedhowtoaddwhenyouwerelittle.So,ifsomeoneaskedyoutoadd18452/3to
7931/5,youwouldbeabletofigureouthowtodoit,eventhoughit'sprettyunlikelythatyou'veadded18452/3to
7931/5everbeforeinyourlife.Thisisbecauseyouarefamiliarwithsomebasicgroundrules:what+andsigns
mean,howtodofractions,thegeneralmethodologyforadding(carryingnumbersandallthat).Thedifferenceisthat
youdoarithmeticinelementaryschoolandorganicchemistryincollege.Theprinciples,thegroundrules,andthe
methodsoforganicchemistryaregoingtogobyquickly,andyou'regoingtohavetolearnthemwellenoughtomake
useofthem...quickly.

2.N.E. Schore, "Study Guide and Solutions Manual for Organic Chemistry", W.H. Freeman and Co., New York, NY,
1987

LECTURESCHEDULE(APPROXIMATE)
Day

Date

Topic

ChapterNumber

Monday

1Sept

NoClassesLaborDay

Wednesday

3Sept

Announcements,etc.

Friday

5Sept

Bonding&MolecularStructure

Monday

8Sept

Bonding&MolecularStructure

Wednesday

10Sept

Bonding&MolecularStructure

Friday

12Sept

Bonding&MolecularStructure

Monday

15Sept

FunctionalGroup,IntermolecularForces,IRSpectroscopy

Wednesday

17Sept

FunctionalGroup,IntermolecularForces,IRSpectroscopy

Friday

19Sept

FunctionalGroup,IntermolecularForces,IRSpectroscopy

Monday

22Sept

Acids&Bases

Wednesday

24Sept

Acids&Bases

Friday

26Sept

Acids&Bases

Monday

29Sept

Acids&Bases

Wednesday

1Oct

Exam#1

Friday

3Oct

AlkaneNomenclature&ConformationalAnalysis

Monday

6Oct

AlkaneNomenclature&ConformationalAnalysis

Wednesday

8Oct

AlkaneNomenclature&ConformationalAnalysis

Friday

10Oct

AlkaneNomenclature&ConformationalAnalysis

Monday

13Oct

NoClassesColumbusDay

Wednesday

15Oct

AlkaneNomenclature&ConformationalAnalysis

Friday

17Oct

AlkaneNomenclature&ConformationalAnalysis

Monday

20Oct

Stereochemistry

Wednesday

22Oct

Stereochemistry

Friday

24Oct

Stereochemistry

Monday

27Oct

IonicReactions

Wednesday

29Oct

IonicReactions

Friday

31Oct

Exam#2

Monday

3Nov

IonicReactions

Wednesday

5Nov

IonicReactions

Friday

7Nov

Alkenes/AlkynesI

Monday

10Nov

Alkenes/AlkynesI

Wednesday

12Nov

Alkenes/AlkynesI

Friday

14Nov

Alkenes/AlkynesII

Monday

17Nov

Alkenes/AlkynesII

Wednesday

19Nov

Alkenes/AlkynesII

Friday

21Nov

Exam#3

Monday

24Nov

NMR&MassSpec

Wednesday

26Nov

NMR&MassSpec

Friday

28Nov

NoClassesThanksgivingRecess

Monday

1Dec

NMR&MassSpec

Wednesday

3Dec

NMR&MassSpec

Friday

5Dec

RadicalReactions

10

Monday

8Dec

RadicalReactions

10

Wednesday

10Dec

RadicalReactions

10

Friday

12Dec

Exam#4