Review Sheet for CHM 266 at IPFW
Review Sheet for CHM 266 at IPFW
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Date Created: 02/06/15
Organic Chemistry Lab CHM 266 Spring Semester 2007 Science Building 451 800 1100 AM MW IlliiiL illIIIIIIIIII lnstructor Dr Tahmassebi Office Science Building 484 Phone 481 6297 Email tahmassdipfwedu Text Introduction to Organic Laboratory Techniques a small scale approach 2ndEdition by D L Pavia G M Kriz G S Lampman and R G Engel Saunders College Publishing 2005 Lab Separates The Synthesis of A Superabsorbent Polymer Charles M Garner Chemical Education Resources 2000 Tentative Schedule of Experiments Changes may occur but you will be given suf cient notice Experiment Title Reference 1 Oxidation of Cysteine to Handout Technique 255 Cystine Synthesis 20 pt pp 878882 2 Multistep Synthesis Synthesis 40 pt Part 1 Coenzyme Synthesis of Pavia Exp 34A pp 288 Benzoin 294 Review GCMS notes Experiment Title Reference Part 2 Benzil Pavia Exp 348 pp 294 296 Technique 256 pp 882886 Part 3 Tetraphenylcyclopentadienone Pavia Exp 35 pp 300302 3 Synthesis and Recrystallization Handout of Adipic Acid Synthesis 20 pt 4 Free Radical Chlorination Handout Review Analytical 20 pt Technique 22 pp 837 857 5 The Synthesis of a Lab Separate Superabsorbent Polymer Synthesis 20 pt 6 Friedel Crafts Acylation Pavia Exp 59 pp 530 Synthesis 20 pt 537 Technique 161 28 pp 764772 778779 7 Triphenylmethanol Synthesis Pavia Exp 36 pp 303311 20 pt 8 Mutarotation of Glucose Handout Review Analytical 40 pt Technique 23 pp 857 866 9 Nitration of methyl benzoate Pavia Exp 43 pp 352357 Synthesis 20 pt 10 Esteri cation Design of Handout Procedure Synthesis 40 pt 11 Carbohydrate Reactions Pavia Exp 52 pp 443452 Analytical 20 pt 12 Identi cation ofan Organic Handout Unknown Analytical 40 pt Grading 12 Reports 320 points Notebook 130 points Technique 50 points Quizzes 100 points Lab Exam Friday May 4 8 10 AM 100 points Total 700 points Cutoffs gt 90 630 gt 80 560 gt 70 490 gt 60 420 F l lt60 420 Generally the grades tend to be A s or B s with an occasional C if someone really struggles with most ofthe experiments This is only true if all reports are turned in as complete as possible and the notebook is complete Then C s D s and F s become very liker Although I have been somewhat slow returning graded reports you should know how you are doing after the midpoint ofthe semester It is UQ to you to keep track of your qrade and performance I will rarely make a point to tell you what your grade is at a given point Your nal grade should not come as a surprise The above schedule is tentative and depending on the available time some other experiments will be added to this list or some experiments will be modi ed Reports Each lab report will be worth the amount indicated above The format will vary with the experiment Due dates will be announced Both the format and dues dates will be provided on the CHM 266 home page Grading in the reports will be largely based on the results ofthe experiment In a few cases lling out the Organic Preparations card and attaching the appropriate spectra will be suf cient Spectra can be stapled to the card Also products of reactions will be turned in with the report In other experiments a short paper 1 page or less or answers to questions in the experiment will be required Each person will be allowed up to 1 late report Once the limit is reached the following policy will apply 5 ofa particular lab report grade will be deducted for each day it is late up to one week when a grade of zero is awarded However under no circumstance will a report be accepted ifl have already returned graded reports to the class No reports will be accepted after May 15 Of course it should be assumed that items such as your name and complete titles for tables and plots should appear in your report without being speci cally instructed Molecular structures must be generated by computer software like ChemDraw Chemsketch or ISISDraw Links for downloading this free software will be provided on course web page Extraneous marks and smudges should not appear on data spectra chromatograms Except forthe prep cards the reports must be typed As mentioned you will occasionally be asked to answer questions or write a short paper on a topic for lab reports In those cases I don t mind and actually encourage you to work together In fact you may ask me questions to insure that you receive the highest possible score However I do expect that you write answers in your own words to the best of your ability I will deduct points in reports for answers that have the exact same wording In the end the point is to learn how to conduct experiments in organic chemistry lfyou can learn from each other that s great However quickly copying an answer is not learning Lab reports are due the rst 15 minutes of lab on the announced date After that the report is considered late You can not complete your report in lab Technique You will be graded on your safety practices and the skill with which you perform experiments This technique grade will be assigned at the end ofthe semester Normally I will take the total grade of your reports divide that by the total possible report grade and multiply by 50 Yourtechnique grade would then re ect how well you performed the lab and knew the material However I reserve the right to deduct points from this value ifthe following reasons 0 Safety practices as described in the safety sheets notes and lab manual are not followed This particularly includes not wearing goggles 0 Suggestions by the instructor for experimental procedure or apparatus setup are not followed 0 Student samples stored in the refrigerator or drawer are not properly labeled 0 The caps of reagent bottles have not been replaced after use 0 Reagents and solvents have been contaminated This can be avoided by not replacing unused reagent or solvent to their original containers Place unused material in the waste bottles Also you should not directly pipet reagents and solvents from bottles Pipets that have not been cleaned and dried have been a cause of contamination previously Pour liquids into a beaker or ask and then use the pipet lfyour pipet is dirty it affects only your experiment and not others 0 This requires that you minimize how much material is poured out so that we don t waste expensive chemicals and don t unnecessarily add to the waste that must be disposed 0 Magnetic stirrers hotplates water faucets gas lines mp and air lines have not been shut off Hood sashes have not been closed The mp apparatus and balances should be turned off at the end ofthe lab period ifyou are the last to use them Reagents and equipment are not properly replaced to their shelfor drawer location A student has a higherthan usual rate of equipment breakage The instruments have not been treated with care lfwater is to be used for your experiment otherthan a hot or cold water bath always use the deionized water from the gray faucets After cleaning glassware and equipment with tap water always rinse with deionized water There are suf cient contaminants in tap water used for lab to adversely affect experiments I have chosen experiments that generally work well despite whatever mistakes are made but it is always good technique to use deionized water The number of points deducted will be determined by the instructor and announced to the student This policy is not meant to be punitive but to help you become competent in lab Although you will see some ofthese techniques in later lab courses CHM 265 and CHM 266 are essentially designed to be the only courses where you will learn to function in a lab that does organic chemistry When you get to a job you may be expected to perform recrystallizations and distillations lfyou don t learn it here you won t impress your coworkers and bosses by learning it on the job later Notebook You will be required to keep a laboratory notebook using the following guidelines 1 A bound notebook must be used 2 A table of contents must be placed at the beginning ofthe notebook Numberthe pages ofthe notebook if necessary 3 Use only pen in recording entries 4 When making corrections place a single line through the error eg Then 4Qml8 ml of ethanol was 5 Mark the date of each new notebook entry 6 Two types of experiments will be performed throughout the course Either you will synthesize and isolate a compound synthesis experiment or you will perform a speci c laboratory technique or analytical test analyticaltechnique experiments The notebook entries for each type of experiment will be somewhat different For analyticaltechnique experiments use the following format AnalyticalTechnique Notebook Entries a Place the title ofthe experiment at the top ofthe page b Write the reference for the procedure See last two pages for preferred style 0 Write out a table containing the names ofthe compounds used pertinent known analytical data such as mp bp etc obtained from the CRC Handbook of Chemistry and Physics Merck Index or Chem nder and any particular hazards presented by the compound Under hazards indicate whether the compound is known to be toxic ammable explosive an irritant etc obtained from the Sigma Aldrich Library of Chemical Safety the Merck Index or Chem nder This information may appear on the bottle39s label d Write the procedure you used to perform the experiment in full English sentences Avoid the use of the pronouns l we and they Place the date on which that portion of the procedure was performed on the lefthand side at the beginning of the narrative Be concise but include enough information so that anyone can read your notebook and do the experiment e Place all data collected masses mp bp in a separate data section Do not mix data with the narrative Also clearly indicate your nal results Write the date on which the observations were made on the lefthand side at the rst entry for that day See the example given Synthesis Experiment a Place the title ofthe experiment at the top ofthe page b Write out the reactions performed directly below the title 0 Write the reference ofthe procedure See last two pages for preferred style d Write out a table containing the names of the compound used their molecular weights the amount of each compound used the number moles of each compound used and pertinent analytical data known about the compound and its known hazards For the product of the reaction write the theoretical yield in grams and moles on the table Upon completion ofthe experiment write the actual yield and percent yield below them e Write the procedure section in the manner described above f Write the data section in the manner described above At the moment I plan to check the notebooks on a weekly basis The total notebook grade will be 130 points at the end ofthe semester In general notebooks are not meant to be works of great literature However organic chemistry notebooks are meant to allow anyone to successfully repeat an experiment The procedure section and handwriting should be clear enough that any chemist could read it and perform the experiment As a result I will not always correct grammar or spelling However ifa misspelling or poor grammar could result in someone making an error and then points will be deducted Also ifan error would make you look particularly unprofessional if made in an industrial or research lab setting then points will be deducted Note sometimes the same information will appear more than once in a given notebook entry For example yield will appear in the table in the beginning ofthe experiment and in the data section Examples of notebook entries are provided at the end ofthe syllabus Quizzes and Final Exam Announced quizzes 10 to 30 pt each and a nal lab exam will be given They will cover practical aspects of organic chemistry some theory and aspects ofthe experiments you are performing The quizzes will be preparation for the nal The nal will be Friday May 4 800 1000 AM It has already been asked No you may not work together on quizzes and the nal like you may forthe lab report questions Other comments about the course If an error is corrected and no points are lost this means that you should avoid this error in the future If the same error is made later points may be lost Although you may help each other each student or pair of students where appropriate is expected to provide their own data and samples for each lab report Each student is expected to provide a separate and unique lab report unless you are working as pair as designated for a given experiment Unauthorized use of another student s data or reports will not be tolerated I reserve the right to take 1 ofthe three following actions 0 You will receive 0 points for a given section ofthe report 0 You will receive 0 points for the entire report 0 You will receive an F for the course You should realize that each instrument s output consists of a certain amount of irreproducible electronic noise The probability that the same instrument will give the same exact results twice is negligible On time attendance is expected at all ofthe lab sessions One point will be deducted for tardiness of 15 minutes from yourtechniques grade lfyou are more than halfan hour late you are not allowed to come in to the lab All cell phones must be turned off in the lab lfyour phone rings during lab session one point will be deducted from yourtechniques grade Although not required yet some schools and instructors require outlines of procedures to insure that experimental procedures have been read If it appears that some students are not coming prepared to lab it may become a requirement Procedure changes and announcements for the course will be given in lab and on the CHM 266 Home Page Lectures explaining the experiments practical considerations in organic chemistry and some theory will be given on many but not all lab periods The notes will be presented on transparencies You have been provided with the notes forthe rst two lab lectures The remaining lectures for the semester must be printed from the internet See the CHM 266 Home Page Use the computers on campus for your printing needs It is your responsibility to have these materials ready prior to lab You can use the computer in Organic lab to look up compound properties on wwwchem ndercom and other necessary information but may not print It is required to save your data on a zip disk preferably 100 MB and bring it to lab You will be assigned a drawer and a hood forthe semester The locker will be only yours but the hood will be shared with other laboratory sections You will be expected to clean your hood at the end of each lab period Your drawer will be expected to be clean at the end ofthe semester Clean it on a regular basis so that it does not become stained The stockroom personnel are very busy please do not make extra work forthem Return all chemicals and equipment back to their proper locations Clean up after yourselves In several ways organic chemistry lab is much different than general chemistry lab In certain ways organic chemistry lab re ects what it39s actually like to work in a lab more than general chemistry 0 Most experiments will last more than one lab period c Often you will be working on more than one experiment at once 0 lfyou make a mistake and the experiment doesn39t work it will have to be repeated until it does work 0 The experiments involve techniques used by people who do organic chemistry part or all ofthe time distillation recrystallization re ux IR NMR etc I can39t or won39t necessarily stay late or show up early to accommodate your schedule vou don39t qet the experiment done bv the due date because vou did not spend all the time in lab vou could for it then that39s vour problem I realize that some students have dif cult schedules Forthat reason I am trying to be as exible as possible In the end however you must complete the same amount of work as everyone else Occasionally you may have to wait for a particular reaction to nish or you may complete a procedure early This is a good time to work on your notebook reports or other experiments It is not necessary but may be helpful to write an outline ofthe experiment before you do it People often nd that it takes less time to do the experiment and fewer mistakes are made I often do this myself To re ect more stringent safety requirements imposed by various governmental agencies you will be required to label all samples that are to be stored in your drawer or refrigerator Using one ofthe labels with the 4color hazard diamond write down the name ofthe compound the date and your initials Then when available write the hazard numbers in the appropriate boxes Further explanation will be provided in lecture Please always place your thermometers with the bulb pointing downwards in the plastic tubes mounted on the inside of your lockers You will be expected to know the following from general chemistry lab These topics will not be covered in lab lecture this semester Either read the appropriate section in your lab manual if you have forgotten or ask me questions 0 How to calculate molecular weights How to calculate limiting reagents How to calculate theoretical yields How to calculate yields How to use a balance and measure masses How to use graduated cylinders volumetric asks and volumetric pipets How to use Bunsen burners Useful References 1 R C Weast ed quotCRC Handbook of Chemistry and Physicsquot 70th ed CRC Press Boca Raton 1989 revised annually 2 S Budavari ed quotThe Merck Indexquot 12th Ed Rahway NJ Merck amp Co 1996 3 J Nagarkatti C Lane quotAldrich Catalog and Handbook of Fine Chemicalsquot Aldrich Chemical Co Milwaukee 1992 4 R E Lenga ed quotThe SigmaAldrich Library of Chemical Safety Data Edition quot Aldrich Chemical Co Milwaukee 1998 5 C J Pouchert quotAldrich Library of Infrared Spectraquot 3rd Ed Aldrich Chemical Co Milwaukee 1981 6 ChemFinder Database and Internet Searching www Chemfinder com 7 NIST Chemistry WebBook httpwebbooknistgov The IPFW Organic Chemistry Resources Page also contains links to useful references In particular Material Safety Data sheets MSD can be obtained which may be helpful for entering hazards into the notebook A will Tan T Cl nbx u MoTQbml t EH isolg vx ofGQim y 0 C93 cm i 0 ByC C LF LW quot H Ha z Labom op lnlanmbl Gym C CJ tQrnJr Z Eg A LLV SC ga Lom 1W7 amigo cwde NOLAhi thal likal HOLZGLr0k5 cmCCegm k 23 squirm neat rm fodlum OaKIQ OhCL Iijk VHF 0 go 39 39 Mamba 0N0 50 3235C all 337wl 5 D39 50 were W Ma ioublc QCKNQSS omc lo ifgl calfmull m a 5 0 comm 0 00 o 3930 Jam Ccu mate am 150 mi arts 1 Wucmijlmglf ne was Aimt QDP QC ml x CC on clhbn WMJ 1A2 ha anal of Ed fw rc we wax M PQ uZ jr y39 row mOlLCbrtgltCQI quot 5 m5 JQu QZ rom ML Syrmvd39llt Bp39er IMTU ebook E Try 39 10 rtparc d x m 0 616quot CHth mjml 9 95 CH3 gt 0 CI gt ago 1 H LO z cHi5 35 0H3 R413 quot H HoarFEHLCL Pod Y j 0Y2 5 agg d bmd Hobk zkkgm OMZCFQ yfjn k FORf 330731 Bafbw 140C Cl nd 41 a 3 r am 0 w Moles 6 d awlugt1 21 my 05 was omj 39l amma j q J Como kfdrodxtomcadci 36 lam all 5Mr7mml 35 r 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