CHEM345-ORGANICCHEMISTRY–I Fall2019Instructors:
Dr.CliffBerkman,Fulmer477(Section1) Dr.RockMancini,Troy222(Section2) [email protected] [email protected]
Prerequisite:AlettergradeofCorbetterinCHEM102orCHEM106ortheequivalentcoursetransfer.Contacting Instructors and TAs: Contact by email only. All instructor and TA email addresses are listed on theBlackboardcoursewebsite.Pleaseput“CHEM345”inthesubjectfieldoftheemail.Pleasedonotcall.OfficeHours:
• TAofficehoursareheldinTroy305.AschedulewillbepostedonthecoursewebsiteaswellasonthedoortoFulmer318nolaterthanthefirstweekofclass.
• Dr.Berkman:M/W/F12:00-1:00pm,Fulmer477 Dr.Mancini:W10:00am-1pm,Troy222ClassMeeting:
• Section1M/W/F11:10-12:00pmFulmer226 Section2M/W/F1:10-2:00pmHealdG3 • Pre-Labmeetingtimesdependonsection.AllPre-LabmeetingsareheldinFulmer438.• WorksheetLab(seeLabschedule):TA’swillbeavailableinTroy305duringLabtimestoanswerquestions.• FirstLabMeeting:AllLabsmeetinFulmer438beginningtheweekofAugust26th.
CourseWebsite:AllcoursematerialisonourBlackboardwebsiteat:
• http://learn.wsu.edu• ThereisacourseFacebookgrouppageat:http://www.facebook.com/groups/chem.345Postingaquestionon
theFacebookpageisawaytoreceiveanansweroutsideofofficehours.RequiredCourseMaterials: Digitalaccess to JohnMcMurry’sFundamentalsofOrganicChemistry (7thEdition)withOWLforonlinehomeworkareincludedinyourcoursefeeandavailableviathecourseBlackboardwebsite.Thissystemdoesnotusecodes.Seehttps://firstday.wsu.edufordetails. ForOWL Support issues, see the “eBook andHomework” folder on the courseBlackboardpage - help canbe foundunder“CengageTechnicalSupport.”You will also need an organic chemistry model kit. An inexpensive yet very good model kit is found at:http://www.maruzen.info/hgs/catalog/product_info.php?products_id=653. A slightly larger version is found at:http://www.maruzen.info/hgs/catalog/product_info.php?products_id=654.ModelkitscanalsobepurchasedoneBayorAmazonforareasonableprice.Itisessentialyouhaveamodelkitbeforethefirstexam.CourseObjectivesandDescription:StudentscompletingCHEM345willbeableto:
1) Rationalizemolecularreactivitybasedonfunctionalgroups,2) MasterthefoundationalknowledgenecessaryforsuccessinCHEM348,3) Critically evaluate simple Laboratory methods dealing with compound
separation,identification,andsynthesis.4) Safelymanipulatechemicalcompoundsandunderstandchemicalhazardsin
theLaboratory.
LECTURECOURSEDESCRIPTION: TheCHEM345curriculumisbasedonthe“surveyoffunctionalgroups”approachtoteaching organic reactions andmechanisms. Each week we will be exploring a different type of organic compound.PleaseconsultthelecturetopicoutlinesectionofthecoursewebsiteandkeepupwithreadingandHomework.LectureSchedule&Topics:WewillcoverChapters1–11inthetext.LectureslideswillbepostedonBlackboardandshouldbereviewedinadvanceofLecture.Week Starting Monday Tuesday Wednesday Thursday Friday1 August19 Ch.1 Ch.1,Ch.2 Ch.22 August26 Ch.2 Ch.3 Ch.33 September2 LaborDay Ch.4 CH.44 September9 CH.4 Ch.4 Ch.45 September16 Ch.5 Ch.5 Ch.56 September23 Ch.5 REVIEW EXAM1,6-8pm Ch.67 September30 Ch.6 Ch.6 Ch.68 October7 Ch.7 Ch.7 Ch.79 October14 Ch.7 Ch.7 Ch.810 October21 Ch.8 Ch.8 Ch.911 October28 Ch.9 Ch.9 Ch.912 November4 Ch.9 REVIEW EXAM2,6-8pm Ch.1013 November11 Veteran’sDay Ch.10 Ch.1014 November18 Ch.10 Ch.11 Ch.1115 November25 ThanksgivingVacation16 December2 Ch.11 Ch.11 REVIEW17 December9 FINALEXAM,7-10pm
Student-LearningOutcomes:
1. Usechemicalacid/basereactivitytopredictchemicalequilibrium.2. Describe chemical reactivity in terms of organic functional group chemistry, including functional group
transformation.3. Interpretstructuralchangeswithinachemicalframeworkconsideringbondmakingandbondbreaking.4. Proposereasonablemechanismsthatconvertstartingmaterialstoproduct5. Interpretstereochemicaldatathatinformsamechanistichypothesis.6. Plananorganicsynthesisusingaretrosyntheticapproachbasedonknownchemicalreactions.7. Developskillinsafechemicalhandling,measurements,experimentaltechnique,andsimplesynthesis.8. Plansimplecompoundseparationschemesusingsolubilitycharacteristics.
Assessment: Student-Learning Outcomes 1 through 7 will be assessed using graded exams and homework. AnychemicalseparationstheorynecessarytoStudentLearningOutcome8willalsobeassessedusingexams.Theremainderofoutcomes7and8willbeassessedbygradedLabReports.Assignments&GradingPolicy:ThiscoursewillbegradedonthebasisofHomework,twoEXAMS,acomprehensiveFINALEXAM,andLab.• Homework=10%ofyourgrade.WewillbeusingOWLforonlinehomework.Allassignmentswill
be accessible through Blackboard Learn. Your lowest homework score will be dropped. Inaddition, Homework problems from the end of each chapter will be assigned but not graded.EXAMquestionswillbebasedonbothOWL&end-of-chapterHomeworkproblems.
• EXAMS=each20%ofyourgrade:TwohourlyEXAMSwillbeadministered.Previousexamsareprovidedonthecoursewebsite. Ifyoumiss(orperformpoorly)onanEXAM,thatscorecanbedroppedandyourfinalwillcountat45%.EXAMquestionswillbebasedonbothOWL&end-of-chapterHomeworkproblems.
• FINAL EXAM = 25% of your grade: A two-hourmandatory final exam (comprehensive) will beadministeredat theendof the course. TheFINALEXAM is required topass this course. FINALEXAMquestionswillbebasedonbothOWL&end-of-chapterHomeworkproblems.
• Lab=25%ofyourgrade:Completing10(outof12)Labsisrequiredtopassthiscourse.
GradingScale
A 92-100
A- 89-91
B+ 86-88
B 83-85
B- 80-82
C+ 77-79
C 72-76
C- 69-71
D+ 65-68
D 61-64
F <60
GradeSummary: Yourtotal scorewillbecalculatedusingtwomethods togiveyouthebestpossibleoutcome.First,yourtotalscorewillbecalculatedusingall fivegradingcomponents: Homework,EXAM1,EXAM2,FINALEXAM,Lab.Second,yourtotalscorewillbecalculatedusingonlythreegradingcomponents: Homework,FINALEXAM,Lab. Yourletter grade will be based on the best of these two total scores. Two examples are shown below illustrating thedifferencebetweenthesetwomethods.Thefirstexampleshowsatotalscoreof75.5(roundedto76)thatcorrespondstoalettergradeofC.ThesecondexamplecalculatesthetotalscoreusingonlytheHomework,FINALEXAM,andLab.Thissecondcalculationgivesanoverallscoreof81,whichcorrespondstoalettergradeofB–.
samplecalculation#1gradedcomponent weight yourscore
weight weightedscore
1.Homework 10% 90% x 0.10 9.02.EXAM1 20% 63% x 0.20 12.63.EXAM2 20% 62% x 0.20 12.44.FINALEXAM 25% 75% x 0.25 18.85.Lab 25% 91% x 0.25 22.8
total 100%
1.00 (Cgrade)75.5 samplecalculation#2(FINALEXAMalone)
gradedcomponent weight yourscore
weight weightedscore1.Homework 10% 90% x 0.10 9.02.FINALEXAM 65% 75% x 0.65 48.83.Lab 25% 91% x 0.25 22.8
total 100%
1.00 (B-grade)80.5ExamSchedule:AllEXAMSareintheevening.OfficiallyapprovedandschedulednightexaminationshavepriorityovereverythingexceptofficiallyscheduledlecturesandLabs.Ifyouareoff-campusduetoaUniversity-sponsoredevent,youmayarrange foranacademiccounselor toproctor theEXAM-youmustmake thesearrangementswithin the first2-weeksofthesemester.Ifyouhaveavalidconflictwithanothereveningacademicactivity(e.g.abiologyorphysicsLabcourse),youmustarrangeforanalternatetesttimeatleast2-weekspriortotheExam.EXAMS1and2arewrittenforastandard1-hourtimeframesoitispermissibletostartEXAM1orEXAM2upto7:00pmandstillhavetimetocompletethem.TheFINALEXAMiswrittenforastudenttocompletein90minutes.
• EXAM1 ThursdaySeptember26 6:00to8:00pm LocationsTBD• EXAM2 ThursdayNovember7 6:00to8:00pm. LocationsTBD• FINALEXAM TuesdayDecember10 7:00to10:00pm. LocationsTBD
Wedonotgivemake-upexams.ThereisnopenaltyformissingasinglehourlyEXAM.IfyoumissonehourlyEXAM,theweightoftheFINALEXAMwillincreasefrom25%to45%.EXAMPolicy&EXAMRe-grades:BringonlyyourstudentID,amodelkit,andpencilstotheEXAMS.Youwillbeprovidedscratch paper. Youmay not bring any electronic or internet connected devices to the exam. Do not bring or leavevisibleanynotes.fyouareobservedusinganyelectronicdevice,readingofffellowstudent’stests,orusingnotes,youwillFailtheEXAMandbeaskedtoleavethetestingroom.SuchactionisinterpretedasabreachofacademicintegrityandwillbereportedtotheOfficeofStudentConduct.OncetheEXAMSaregraded,theywillbedistributedelectronicallyusingCrowdmark. Lookover theexamcarefullyandmakesurethepointshavebeenaddedcorrectly. IfyoufindanerrororhaveaquestionaboutthegradingoftheEXAM,completeaRe-gradeForm(foundonthecoursewebsite)andemailthiscompletedformtothecourseinstructorwithin2-weeksoftheExam;Re-gradessubmittedafterthattimewillnotbereviewed.BeveryclearwhencompletingtheRe-gradeForm.Forexample,“thereisanerrorinmytotalpoints”or“onquestion2,Idrewthecorrectintermediatestructure...”Avoidrequestssuchas,“IthinkIdeservemorepoints.”
LABCOURSEDESCRIPTION:CHEM345hasaLaboratorycomponentthatmeetsonceperweekfor3hours.Youarenotrequired to purchase any Labmanuals as all printed materials are freely available on the course website. You arerequiredtopurchaseaLabcoataswellasgoggles.Thereareatotalof12LabsthroughouttheFall2019semester.YouMUSTcomplete10ofthe12Labsinordertopassthecourse.Ifyoumissmorethan2Labs,youwillautomaticallyandimmediatelyFAILthecourse.YourLabgradewillbebasedyourbest11LabReports.Therefore,youcanmiss1Labanditwillnotcountagainstyourgrade.However,ifyoumiss2Labs(i.e.,completeonly10Labs),youwillreceivea0(zero)foroneofthemissedLabs.Ifyoucompleteall12 Labs, you will receive EXTRA CREDIT for the 12th Lab. A COMPLETE Lab Report consists of a pre-Lab (20%), aprocedure(20%),andadiscussion/conclusion&post-Labquestions(60%).Before each wet-Lab, you will be expected to fill out the pre-Lab template, which consists of safety information, ahypothesisorquestiontobeanswered,andrelevantreactionmechanisms. Thispre-Labwillbeturned-inandgradedduringthepre-Lablecture.Thepre-Labtemplateis20%ofyouroverallLabReportgrade.Eachwet-Labwillbeginwithasafetybriefingandatutorialat thestartofyourscheduledLabtime inFulmer438 -attendanceisMANDATORY.Ifyouaremorethan10minuteslatetothescheduledtutorial,youwillnotbeallowedtoentertheLaboratoryandyouwillmissthisLab(i.e.,itwillberecordedasamissedLab).DuringLab,youwillbeexpectedtodocumentthestepstakenduringLab. Youwill followtheLabProtocolandwritedownyourprocedureduringLabaseachstepisperformed,aswellasanyrelevantobservations.ItisrequiredthatyourTAsign-offonyourprocedurebeforeyouexittheLab-thiswillbeworth20%ofyouroverallLabReportgrade.AfterLab,abriefdiscussion/conclusionandpost-Labquestionswillbecompletedthatwillbeworththeremaining60%oftheLabReportgrade.Lab Reports are due ONEWEEK from the date of the Lab. Again, a COMPLETE Lab Report consists of a pre-Lab, aprocedure,andadiscussion/conclusion&post-labquestions. Youwill turn inyourCOMPLETELabreportduring thepre-Lab lecture of the following Lab. Theduedate for someLab reportswill be adjusted in theeventof emergencycampusclosureorholidays-thesecaseswillbediscussedduringpre-Lablecture.LabReportsturnedinaftertheduedatewillbescoredasa0(zero)butcountedasacompletedLab.WorksheetLabs.Thereareno tutorials forworksheetLabs. However,yourTAwillbeavailable inFulmer318duringscheduled Lab times in order to assist youwith any questions. Similar towet-Labs, you are expected to turn-in thecompletedWorksheetONEWEEKafteryourscheduledLabperiod.
LabScheduleforCHEM345,FALL2019Week Dates Lab1 Aug19-23 NoLab–FirstWeekofClass2 Aug26-30 IntroDay/LabCheck-in3 Sept2-6 AcidBase4 Sept9-13 TechniqueDay1-Characterization5 Sept16-20 TechniqueDay2-Extraction6 Sept23-27 IsolationofCaffeine7 Sept30-Oct4 NitrationofMethylBenzoate8 Oct7-11 NucleophilicSubstitution9 Oct14-18 2-ComponentExtraction10 Oct21-25 ReductionofaKetone11 Oct28-Nov1 Esterification12 Nov4-8 AldolCondensation13 Nov11-15 StereochemistryWorksheet14 Nov18-22 Saponification/Checkout15 Nov25-29 NoLab-ThanksgivingBreak16 Dec2-6 NoLab-DeadWeek–FinalGradecheck17 Dec9-13 NoLab-FinalExams
AttendancePolicy: Lectureattendancewill notbe recordedor countedas a grading component, however, studentswhowishtosucceedinthiscoursearestronglyencouragedtoattendlecture. Labattendanceismandatoryasstatedabove.Students with Disabilities: Reasonable accommodations are available for students with documented disabilities orchronicmedicalconditions. Ifyouhaveadisabilityandneedaccommodationsto fullyparticipate inthisclass,pleasevisit the Access Center website to follow published procedures to request accommodations:http://www.accesscenter.wsu.edu. Studentsmay also either call or visit theAccess Center in person to schedule anappointmentwithanAccessAdvisor. Location:WashingtonBuilding217;Phone:509-335-3417. Alldisability relatedaccommodationsMUSTbeapprovedthroughtheAccessCenter.Studentswithapprovedaccommodationsarestronglyencouragedtovisitwithinstructorsearlyinthesemesterduringofficehourstodiscusslogistics.AcademicIntegrity:Academicintegrityisthecornerstoneofhighereducation.Assuch,allmembersoftheuniversitycommunity share responsibility for maintaining and promoting the principles of integrity in all activities, includingacademic integrityandhonestscholarship. Academic integritywillbestronglyenforced inthiscourse. StudentswhoviolateWSU’sAcademicIntegrityPolicy(identified inWashingtonAdministrativeCode(WAC)504-26-010(3)and-404)willFailthecourse,willnothavetheoptiontowithdrawfromthecoursependinganappeal,andwillbereportedtotheOfficeofStudentConduct.Cheating includes, but is not limited to, plagiarism and unauthorized collaboration as defined in the Standards ofConductforStudents,WAC504-26-010(3). Youneedtoreadandunderstandallofthedefinitionsofcheating. Ifyouhaveanyquestionsaboutwhatisandisnotallowedinthiscourse,youshouldaskcourseinstructorsbeforeproceeding.If you wish to appeal a faculty member's decision relating to academic integrity, please use the form available atconduct.wsu.edu.SafetyStatement:ClassroomandcampussafetyareofparamountimportanceatWashingtonStateUniversity,andarethe shared responsibility of the entire campus population. WSU urges students to follow the “Alert, Assess, Act,”protocolforalltypesofemergenciesandthe“Run,Hide,Fight”responseforanactiveshooterincident.RemainALERT(throughdirectobservationoremergencynotification),ASSESSyourspecificsituation,andACTinthemostappropriatewaytoassureyourownsafety(andthesafetyofothers ifyouareable). PleasesignupforemergencyalertsonyouraccountatMyWSU.Formoreinformationonthissubject,campussafety,andrelatedtopics,pleaseviewtheFBI’sRun,Hide,FightvideoandvisittheWSUsafetyportal.AccommodationofReligiousObservances:WashingtonStateUniversityreasonablyaccommodatesabsencesallowingforstudentstotakeholidaysforreasonsoffaithorconscienceororganizedactivitiesconductedundertheauspicesofareligious denomination, church, or religious organization. Reasonable accommodation requires the student tocoordinatewiththeinstructoronschedulingexaminationsorotheractivitiesnecessaryforcoursecompletion.Studentsrequestingaccommodationmustprovidewrittennotificationwithinthefirsttwoweeksofthebeginningofthecourseand include specific dates for absences. Approved accommodations for absences will not adversely impact studentgrades.Absencefromclassesorexaminationsforreligiousreasonsdoesnotrelievestudentsfromresponsibilityforanypartof thecourseworkrequiredduring theperiodofabsence.Studentswhofeel theyhavebeentreatedunfairly intermsofthisaccommodationmayrefertoAcademicRegulation104-AcademicComplaintProcedures.
End-of-ChapterHomeworkProblems*inFundamentalsofOrganicChemistry-7thed.,JohnMcMurry
Chapter1
• Review“SummaryandKeyWords”onPages28-29.• Problems:45,48,52,53,56,58,60,61,64,69 (10questions)
Chapter2• Review“SummaryandKeyWords”onPages69-70.• Problems:44,45,47,52,53,56,59,60,65,68 (10questions)
Chapter3• Review“SummaryandKeyWords”onPages103-104• Problems:30,31,35,42,51,54,55,59,60,61 (10questions)
Chapter4• Review“SummaryandKeyWords”onPages142-143.• Review“SummaryofReactions”onPages143-145.• Problems:28,33,35,36,39,42,46,48,50,51,55,58,59,62,63,64 (16questions)
Chapter5• Review“SummaryandKeyWords”onPage179.• Review“SummaryofReactions”onPages179-180.• Problems:27,33,34,36,37,39,40,48,50,51,57,58 (12questions)
Chapter6• Review“SummaryandKeyWords”onPage214.• Problems:29,32,35,40,41,42,51,53,55,56,57,58,59,61 (14questions)
Chapter7• Review“SummaryandKeyWords”onPage245.• Review“SummaryofReactions”onPages245-246.• Problems:29,30,31,32,33,34,36,38,44,51,52,53,54,55,58,61 (16questions)
Chapter8• Review“SummaryandKeyWords”onPages282-283.• Review“SummaryofReactions”onPages283-285.• Problems:26,33,34,35,36,37,38,39,41,42,43,45,46,47,53,55,57,58,59,60,61,62,65,66
(24Questions)Chapter9
• Review“SummaryandKeyWords”onPages314-315.• Review“SummaryofReactions”onPages315-316.• Problems:25,30,31,33,37,38,39,40,41,42,43,45,46,48,53,56 (16questions)
Chapter10• Review“SummaryandKeyWords”onPages360-361.• Review“SummaryofReactions”onPages361-363.• Problems:35,38,39,42,44,45,47,50,55,56,58,59,60,61,62,63,64,66,68,72 (20questions)
Chapter11• Review“SummaryandKeyWords”onPage394.• Review“SummaryofReactions”onPages394-395.• Problems:24,25,26,34,36,37,38,39,40,41,42,43,44,46,48,49,51,52 (18questions)
*EXAMquestionswillbebasedontheseend-of-chapterproblems.