CHEM 341: Elementary Organic Chemistry
CHEM 341: Elementary Organic ChemistryContact InformationMatt (Doc) Bowman262-2519Chemistry 5232bowman@chem.wisc.edu(Please include Chem 341 in the subject line).3 credits: Lecture 50 min three times per weekDiscussion 50 min once per weekLectureMWF 11:00-11:50 AMRoom: Psychology 113Office HoursScheduledMondays and Wednesdays 12:00-1:15 PM Chem 1371Mondays and Wednesdays 3:30-5:30 PM Chamberlin 2135(or by appointment)Teaching AssistantsMichelle FleetwoodCharnell Longfleetwood@wisc.educchasten@chem.wisc.edu
TextbookEssentials of Organic Chemistry by DewickThe following textbooks are also available in the chemistry library onreserve:Organic Chemistry: A Short Course by Hart, Craine, Hart and HadidIntroduction to Organic Chemistry by Brown and PoonFundamentals of Organic Chemistry by McMurryEssential Organic Chemistry by BruiceThere will be no problems assigned from the textbook. Quite a few ofmy course evaluations in the past stated that they never read oropened the book. I do not recommend this course of action, but I dounderstand it. I chose the DeWick textbook as it covers most of thetopics quite concisely and has good charts/diagrams. It is also quite abit less expensive than the ones listed on the reserve list that can runupwards of 150.TA Office HoursTA office hours on the day following exams will be cancelled as theTA’s will be grading then. TA office hours are held in Chemistry B317(Organic TA Office)Michelle FleetwoodWednesday 12:05-12:55 pm and Friday 12:05-12:55 pmCharnell LongTuesday 2:25-3:15 pm and Thursday 4:35-5:25 pmMatt’s Schedule:Matt Bowman this fall is lecturing for two courses Chem 341 and Chem345. There are 110 students in 341 and 255 students in 345. Mattwill try to keep everything straight, but will not remember necessarilywhich student is in which lecture. Because he has to split his mind todeal with each class, he might not be completely there. There will beweeks in which there will be an exam happening for both classes. Atwhich point, any vestiges of his sanity will disappear and there will bedrool, lots and lots of drool. (His sanity is not being helped muchright now as Matt Bowman is writing in the third person). Please statein any email correspondence with him whether you are in 341 or 345.The answer to your questions may differ significantly. Please bepatient. If he does not respond within 12 hours, try again.Also, he does have a hand in at least one laboratory course (Chem342) so again please be patient.
Powerpoint tutorialsThere is some subject matter that can be best explained by the bookor a simple powerpoint tutorial. These tutorials are available atLearn@UW. Please go through them by the indicated date on thecourse schedule. If you do not have access to powerpoint, there is acomputer lab in Chemistry 1375. These computers have powerpoint.The lab is open from 8:30 am to 6:30 pm Monday through Thursdayand is open from 8:30 am to 4:30 pm on Friday.Video lecturesLearn@UW will host a variety of video lectures. These are typically 510 minutes long. They are there to highlight important concepts orclarify points in organic chemistry.Problem setsThere will be a problem set for each lecture day except for the day ofan exam or the day preceding an exam. These problem sets will notbe graded and are there to help you out. Keys will be available by thenext lecture day on Learn@UW.Practice examsI will make at least three practice exams available for each exam. Theexams will be very similar to the practice exams in terms of directions.Answer keys for these exams will also be available. DO NOT SIMPLYLOOK AT THE KEY. ATTEMPT THE PRACTICE EXAM FIRST.HAVE ANOTHER STUDENT IN THE CLASS GRADE IT AS YOUGRADE THEIRS. DISCUSS DISCREPANCIES AND ONLY THENLOOK AT THE KEY.Quizzes:There will be five quizzes during the semester. They will be popquizzes in discussion or take home quizzes or some combinationthereof. They are each worth ten points and you can drop two. Youcan only take the discussion quizzes in the section you are registeredin. Since you can drop two quizzes, there will be no makeupquizzes.
Discussion SectionsThere is a lot of material to cover, and little time to cover it.Sometimes, what I can briefly cover in the lecture will be bettercovered in your discussion section. In addition, the TAs in this coursehave different experiences in teaching and learning organic chemistry.They may have a different way of looking at a topic. As a result, if youdo not understand something from me, you may understand it fromthem. All discussion sections are held in the chemistry 0-4:204:35-5:252373B351B355B355Charnell LongCharnell LongMichelle FleetwoodMichelle FleetwoodProper use of discussion sections:Make mistakes. People learn from mistakes. Be vocal. Go to thefront of the board and write your answers. If they are correct,congratulations. If they are incorrect, all the better as it gives anopportunity to learn something and help out your fellow classmates.There are many correct answers in organic chemistry (and many moreincorrect ones). The TA’s are there to give insight on the nuances oforganic chemistry.Improper use of discussion sections:Just sitting there.
Grading (As transparent as I can be)The grade will be based on exams and quizzes.The maximum number of points available will be 630 points.ABCDF SIMPLY STATEDIf you earn 90% of the totalIf you earn 77% of the totalIf you earn 57% of the totalIf you earn 40% of the illwillwillreceivereceivereceivereceivean A.at least a B.at least a C.at least a D.So if you receive an 88%, this can be an A, AB, or B depending on thefinal distribution. 89.5% is considered to be 99999999999999999999999999999999999999999999999% is considered to be89%. That is just how it is.The actual lines are determined by a mixture of factors: finaldistribution, the historical grade history of all of the sections of Chem341, the phase of the moon, where the darts end up on the board,improvement in the course, etc There are a few things that I can saywith certainty:The 40% line is a hard line. Any score below that will be an F.Regardless what exam averages are.The C line will never be lowered below 50%. A 52% may be a C or D.Confusion about curves and AB’s and BC’s. The AB range and BCrange is very small. Historically for organic chemistry it is small. Formy classes, it has typically been one or two percentage points.The cutoffs represented above are the curve. This is based on severalsemesters of organic chemistry, so you know how you are doingthroughout the semester. The lines may dip a little, but not much.Especially the A line. The last few times I’ve taught, it has barelybudged. Please do not be surprised if your total points are 85% andyour letter grade is a B. If the lines are lowered, they will be loweredso that 25% of the class will receive at least an AB and 35% ofthe class will receive a B or BC. The DF line will not move andthe C line will never dip below 50%.
Exams:There are four regular exams plus the final exam. Each regular examwill be worth 100 points. The regular exams will be Wednesdayevening exams held from 7:15 to 8:45 pm in a lecture hall to beannounced. Please check your schedules for potential conflicts. Thedates are September 23, October 7, October 28, and November 18.Please notify me of any conflicts so alternative arrangements can bemade. You may not drop any exam.The final exam is worth 200 points and cannot be dropped.It will take place on Thursday, December 17 from 5:05 pm to 7:05pm. Unfortunately, this date is set by the University and I can onlygrant makeup exams in a VERY limited manner such as two examswithin a 24 hour period. Please do not ask for a makeup exam due toairline tickets going home for Christmas. I’m afraid that is not listedas a valid reason.Exam regrade policy: Mistakes in exam grading will occasionally bemade. You will have one week after exams are returned to submit theentire exam for regrading. Keep in mind, since mistakes may or maynot be in your favor, the exam grade can actually be lowered. Alldecisions on the regrades are final. DO NOT UNDER ANYCIRCUMSTANCES CHANGE AN ANSWER AND SUBMIT IT FOR AREGRADE. THIS IS ACADEMIC MISCONDUCT AND WILL BEDEALT WITH HARSHLY.Regrade submittal procedure: Email Matt Bowman that you aresubmitting an exam for a regrade. Write on the exam score sheetwhich problem needs to be regraded and why. DO NOT CHANGEANYTHING ELSE. Place the exam in Matt Bowman’s mailbox inChemistry 1146.
Academic MisconductYou are all adults. There is no reason to cheat, but plenty of reasonsnot to. An F in the course is one of many reasons. Cheat sheets,notes, textbooks, someone else's paper, the internet, cell phones, acrystal ball bearing the disembodied spirit of the Great OrganicChemist R. B. Woodward, etc are prohibited from the exam. Use ofthese prohibited materials during an exam will result in a zero for theexam score. You will only be allowed pencils/pens and model kits forthe exams.A percentage of the exams will be photocopied. Should an answer bechanged and submitted for a regrading, academic misconduct hasoccurred and the perpetrator will receive an F in the course and bereported to the Dean’s office.I have been advised by the staff (some of them legal staff) that Icannot use pepper spray in dealing with wandering eyes. I will try toremember to remind the TAs proctoring the exams of that advice. Ifthe TAs suspect anyone of this condition, they will announce foreveryone to keep their eyes on their paper. If the problem persists,the TAs have the discretionary power to move any student suspectedduring an exam. Exams of adjacent students will be examined, andshould there be ample evidence, lower exam scores including zeroeswill be given to the perpetrator. Please fight against wandering eyes.Please shield your paper the best you can to remove any temptationfrom others.THERE ARE NO ACCEPTABLE EXCUSES FOR ACADEMICMISCONDUCT. I HAVE CAUGHT SEVERAL STUDENTS AND THEYNOW HAVE A DARK MARK ON THEIR PERMANENT RECORD. IHAVE NO SYMPATHY FOR THOSE THAT CHOOSE TO CHEAT.
PhilosophyThis is your education. It is what you make of it. Should at anytimeyou feel that I am going too fast, let me or your TA know. If you donot understand a concept, let me or your TA know ASAP. I've donemy best to pick a set of organic topics that are interconnected, buildon one another, and represent the basics or organic chemistry that areuseful/fun to know regardless of major. If you do not understand atopic, it will continually haunt you through out the course, as theentire course is cumulative.Organic chemistry has been compared to a science, an art, even aforeign language. It is pretty much all of those. In order to succeed inthis course, you will need patience, vigilance, and imagination. Thereare three interlaced components to Chem 341: Structure, Mechanism,and Synthesis.Structure:Mechanism:Synthesis:What does a compound look like? Is it happy?requires imaginationHow and why does a molecule do what it does?requires pattern recognitionCan we get molecules to work together to form anew molecule (preferably of our choosing)?requires strategy
Study tipsOrganic chemistry is very cumulative. Once you start, you cannotstop. (Oh and you need to start right away). Material on exam I willbe tested again on exams II, III, IV, and the Final. Likewise, withsubsequent topics. The problem sets will not only cover currentmaterial but past material as well.Between 1-4 hours after each lecture, start the problem set. Do notwait for the answer key to be posted to start the problem set.Between 4-8 hours after each lecture, recopy your notes for thatlecture. Look for the patterns.In the course schedule, the relevant page numbers from the text arelisted. The exams are going to be based on the material from thelectures, lecture notes, problem sets, and discussions. The text isthere to help you understand the material. I strongly suggest that youread the relevant pages either before or after lecture.Make flash cards. Carry these with you wherever you go.through them throughout each day.FlipA very good way to study is to study in groups. Multiple problem setswill be available to work on along with several practice exams. Isuggest you form groups to study in. You can go about this talking toclassmates in discussion, lecture, etc The sooner you set up thesegroups the better off you will be. If you wish a classroom to meet in, Ican see about reserving one for you.The best way to understand organic chemistry is constant practice.The TA's and I will do our best to provide quite a bit of practice in theform of problem sets and practice exams. Should you find adiscrepancy in what the TA's, book, internet, or myself, please bring itto our attention immediately. It may be a case of a subtlety, anoutright error, or an over generalization. Regardless, we'll try toexplain the discrepancy.
Additional HelpIn addition to the TA's and office hours, there are a couple of placeswhere you can find assistance.The Organic TA Office is in room B317. There is a schedule postedoutside the door of various TA's and when they will be available to helpyou. Feel free to ask any of them for help even if they are not a TA forChem 341.Alpha Chi Sigma Chemistry Fraternity has offered tutoring forchemistry classes in the past. Please contact them about their currenthelp sessions.GUTS offers tutors as well. They can be contacted at:Student Activity CenterOffice #4413333 E Campus MallMadison, WI 53715-1380Phone: 608-263-5666E-mail: guts@rso.wisc.eduThere are also private tutors available. The General Chemistry Office(Room 1328) has a list of tutors and prices. If you do work with atutor, please let them know that I post notes, problem sets, practiceexams, and tutorials on Learn@UW. Anyone can access theLearn@UW Chem 341 site by using the visitor login.They should go to learnuw.wisc.edu and click on visitor login.USER NAME: orgchem.pseudoPASSWORD: orgchem.pseudoThey will be able to access any handouts using that login.A very good way to study is to study in groups. Multiple problem setswill be available to work on along with several practice exams.
1729Substitutions:SN1Pages167- ‐181,183- nantiomersPages73- ‐82,90- ‐92,116- ‐11925Acid/BaseChemistryPages121- ‐126,155- ‐16518125ResonancePages45- ages10- ‐15114FRIDAYSATURDAY2720136SUNDAYChem3411- rating"NH 2 accordingtoWikipedia.Yep,1- 3- ‐20330InClassReviewExamI7:15- ‐8:45PM242316HybridizationNomenclaturePages24- ges19- sPowerpointPages55- ‐72,83- enclaturecyclicalkanesPowerpointPages55- ‐72,83- ‐88TutorialIII147MONDAYSEPTEMBER2015
CarbocationRearrangementsPages439- ives:EstersPages248- ‐2553031CarbonylChemistryIminePages242- ‐24423CarbonylChemistryGrignard/NaBH4Pages235- - ‐203Eliminations:E2Pages378- ‐380and400- as(boilingpoint3 mIII7:15pm- alkenesPages283- ‐286,296- ‐30414262781THURSDAYInClassReviewExamII7- ‐15pm- talPages221- s238- ‐23919Eliminations:E1Pages412- ‐420and436- ‐440125MONDAYOCTOBER2015
30EAS:BrominationPages304- ‐31723Cl24ClClOHEAS:DeuterationPages304- trationPages304- luminumHydride:Pages267- S:EAS:Friedel- ‐CraftsPages304- ‐31725InClassReviewExamIV7:15pm- s240- ‐251,271- onPages319- rboxylicAcidDerivatives:AmidesandNitriles262- ‐2672MONDAYNOVEMBER2015
Cl29281522ReviewEmailtopicstoMattMichaelPages397- 912ClaisenPages379- mStarWars5:05- ownasteargas)isactuallyasolidthatmeltsaround93 C.Typically,itisdissolvedinaninertnon- causestheburningsensation.312417MannichPages369- ‐37210AldolPages357- ‐366NOTES:30231692WEDNESDAYDECEMBER2015
Chem 341: SurveyPlease answer the following questions so I can adapt Chem 341 tobetter suit your needs. Please turn this page in to Matt Bowman'smailbox in Chemistry 1146 by September 12.What is your year? (Freshman, Grad Student, Returning Adult, etc )What is your major?What do you hope to get out of this class? (Besides a good grade)When is the ideal time for office hours (day and time)?Do you learn a lot from textbooks?What other classes are you currently enrolled in?
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Textbook Essentials of Organic Chemistry by Dewick The following textbooks are also available in the chemistry library on reserve: Organic Chemistry: A Short Course by Hart, Craine, Hart and Hadid Introduction to Organic Chemistry by Brown and Poon Fundamentals of Organic Chemistry by McMurry Essential Organic Chemistry by Bru
Chemistry ORU CH 210 Organic Chemistry I CHE 211 1,3 Chemistry OSU-OKC CH 210 Organic Chemistry I CHEM 2055 1,3,5 Chemistry OU CH 210 Organic Chemistry I CHEM 3064 1 Chemistry RCC CH 210 Organic Chemistry I CHEM 2115 1,3,5 Chemistry RSC CH 210 Organic Chemistry I CHEM 2103 1,3 Chemistry RSC CH 210 Organic Chemistry I CHEM 2112 1,3
CHEM 31X. Chemical Principles 4 CHEM 33. Structure and Reactivity 4 CHEM 35. Organic Monofunctional Compounds 4 CHEM 36. Organic Chemistry Laboratory I 3 MATH 41, 42, 51. Calculus, Linear Equations 5 5 5 SECOND YEAR CHEM 130. Organic Chemistry Laboratory II 4 CHEM 131. Organic Polyfunctional Compounds y3 CHEM 134.
CHEM 350B Topics in Chemistry 7.5 454.95 CHEM 351 Chemicals Big and Small: Nano- 15 909.90 CHEM 352 Advanced Concepts in Chemistry 15 909.90 CHEM 352A Advanced Concepts in Chemistry 7.5 454.95 CHEM 352B Advanced Concepts in Chemistry 7.5 454.95 CHEM 360 Contemporary Green Chemistry 15 909.90 CHEM 380 Materials Chemistry 15 909.90
CHEM 0350 Organic Chemistry 1 CHEM 0360 Organic Chemistry 1 CHEM 0500 Inorganic Chemistry 1 CHEM 1140 Physical Chemistry: Quantum Chemistry 1 1 . Chemistry at Brown equivalent or greater in scope and scale to work the studen
Accelerated Chemistry I and Accelerated Chemistry Lab I and Accelerated Chemistry II and Accelerated Chemistry Lab II (preferred sequence) CHEM 102 & CHEM 103 & CHEM 104 & CHEM 105 General Chemistry I and General Chemistry Lab I and General Chemistry II and General Chemistry Lab II (with advisor approval) Organic chemistry, select from: 9-10
bonding and reactions) necessary for courses in elementary organic chemistry and physiological chemistry. Students may only receive credit toward graduation for one of the following: CHEM 10050; or CHEM 10060 and CHEM 10061; or CHEM 10970 and CHEM 10971.
CHEM 110 Chemistry of the Living World 15 4,736.85 CHEM 120 Chemistry of Material World 15 4,736.85 CHEM 150 Concepts in Chemistry 15 4,736.85 CHEM 200 Special Topic 15 4,736.85 CHEM 251 Structure and Spectroscopy 15 4,736.85 CHEM 252 Properties and Analysis of Mat 15 4,736.85
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