1. Revised: 6/11/09HChemistry 333LFall 2009 Instructor: Dr. G. Handy, 7-5188, handy@mail.chem.sc.edu, Office: PSC 218A Senior Teaching Assistant:Gabriel Ross, rossgn@gmail.com, 7-2117, Office: PSC 215 Senior Lab Coordinator: Jeffrey Steen, steenj@mailbox.sc.edu, 7-2117, Office: PSC 215 Meeting Times / Rooms:Section 1, 501 MW 12:20PM- 3:25PM, PSC 219 Section 2, 502 TTh 12:30PM -3:35PM PSC 219 Section 3, 503, TTh 3:30PM- 6:30PM, PSC 219 Section 4, 504, TTh 3:30PM- 6:30PM, PSC 217 Lab Teaching Assistants: TBA Course Goals By the end of the semester students should have: A solid foundation of the application of concepts from the organic chemistry lecture A firm comprehension of the physical processes of organic chemistry reactions Students will be expected to conduct experimental procedures and reaction processes that reinforce the theoretical concepts learned in the lecture course. Improved hand-eye coordination Improved writing skills. The required writing for CHEM 333L includes documentation of both data analysis and error analysis. Pre-lab and post-lab write-ups are required after every experiment. The pre-lab write-ups will document the theory behind the experiment, appropriate mechanisms, the experiment’s procedure, and any other relevant information. Post-lab write-ups will document the results of the experiment, analyze these results, and include any other relevant information. Performed oral presentations in front of the class. This will allow students to improve their public speaking skills and gain confidence speaking in front of others. Successfully performed and analyzed IR Spectroscopy of complex organic molecules. This will entail a strong understanding of the concepts and principles behind IR Spectroscopy and the analysis of structural elucidation of complex organic molecules. Course Requirements: 1. Text: Microscale Experiments in Organic Chemistry, CHEM 333L/334L. Available at Copy Pickup at 1830 Rosewood Drive2. Safety Goggles NOTE: The Lab Safety Packet will be available online at http://www.chem.sc.edu/faculty/handy Infrared Spectroscopy:Students enrolled in 333L will be taught the theory and applications of IR and will be trained on the Perkin Elmer FT IR spectrophotometer. Each student is required to submit original IR spectra as part of the lab report. If laboratory time is unavailable, you are required to work with your TA and arrange a mutually convenient time to record IR spectra of your sample. Failure to do so will result in the loss of points. The course requires the completion of the following experiments: ExperimentDateInfrared SpectroscopyWeek of 8/24-8/28Recitation on RecrystallizationWeek of 8/31-9/4*Expt. 1 Recrystallization (Microscale) Pthalic AcidWeek of 8/31-9/4Expt. 2 Simple Distillation/ Fractional DistillationWeek of 9/14-9/18Expt. 3 Chemical Extraction (Microscale)Week of 9/21-9/25Expt. 4 Thin Layer Chromatography of AnalgesicsWeek of 9/28-10/2Expt. 5 Oxidation of Cyclohexanol to Cyclohexanone (Microscale)Week of 10/5-10/6*Expt. 6 Dehydration of Cyclohexanol to Cyclohexene (Microscale)Week of 10/12-10/16Expt. 7 Reactions to CarbocationsWeek of 10/19-10/23Expt. 8 Phase Transfer CatalysisWeek of 10/26-10/30Expt. 9 Williamson Ether SynthesisWeek of 11/2-11/6Expt. 10 Fischer EsterificationWeek of 11/9-11/13Review for FinalWeek of 11/16-11/17*Final ExamWeek of 11/23-11/24Check Out/ Final GradesWeek of 12/1-12/5 DateLabAssignment DueMonday, Tuesday8/24, 8/25 Safety VideoSafety Practices in the Lab Laboratory Requirements 1. Check-in2. Clean glassware3. Meet with T.A.4. Demonstrations5. Instruction of Waste DisposalWednesday, Thursday8/26, 8/27Recitation: IR Spectroscopy1. Use of Electronic Balance, Mel-Temp Units, Steam Bath and Heating Mantle/Variac, IR trainingMonday, Tuesday8/31, 9/1Quiz: IR SpectroscopyRecitation 1: Recrystallization(Note: Part B for majors only; TA will discuss this with you)Wednesday, Thursday 9/2, 9/3Wednesday, Thursday 9/9, 9/10Quiz 1 – RecrystallizationRecitation 2: A Simple Distillation and Fractional Distillation1. Pre-lab 12. Complete Expt. 1Record IR Monday, Tuesday 9/14, 9/15Wednesday, Thursday 9/16, 9/17Quiz 2 – Simple and Fractional DistillationRecitation 3: A Chemical Extraction1. Pre-lab 22. Post-lab 13. Complete Expt. 2*Record IRMonday, Tuesday 9/21, 9/22Wednesday, Thursday 9/23, 9/24Quiz 3 – ExtractionRecitation 4: TLC of Analgesics1. Pre-lab 32. Post-lab 23. Complete Expt. 3*Record IRMonday, Tuesday 9/28, 9/29Wednesday, Thursday 9/30, 10/1Quiz 4 – TLCRecitation 5 – Oxidation of Alcohols1. Pre-lab 42. Post-lab 33. Complete Expt. 4*Record IRMonday, Tuesday 10/5, 10/6Quiz 5 – Oxidation of AlcoholsRecitation 6: Dehydration 1. Pre-lab 52. Post-lab 43. Complete Expt. 5*Record IRMonday, Tuesday 10/12, 10/13Wednesday, Thursday 10/14, 10/15Quiz 6 - DehydrationRecitation 7: Reactions of Carbocations 1. Pre-lab 62. Post-lab 53. Complete Expt. 6*Record IRMonday, Tuesday 10/19, 10/20Wednesday, Thursday 10/21, 10/22Quiz 7 –Reactions of CarbocationsRecitation 8: Phase Transfer Catalysis1. Pre-lab 72. Post-lab 63. Complete Expt. 7*Record IRMonday, Tuesday 10/26, 10/27Wednesday, Thursday 10/28, 10/29Quiz 8 -Phase Transfer CatalysisRecitation 9: Williamson Ether Synthesis1. Pre-lab 82. Post-lab 73. Complete Expt. 8*Record IR Monday, Tuesday 11/2, 11/3Wednesday, Thursday 11/4, 11/5Quiz 9 - Williamson Ether SynthesisRecitation 10: Fischer Esterification1. Pre-lab 92. Post-lab 83. Complete Expt. 9*Record IR Monday, Tuesday 11/9, 11/10Wednesday, Thursday 11/11, 11/12Quiz 10 - Fischer Esterification1. Pre-lab 102. Post-lab 93. Complete Expt. 10Record IR Monday, Tuesday 11/16, 11/17Review for the Final Exam1. Post-lab 10 Monday, Tuesday 11/23, 11/24FINAL EXAM1. Check Out – MANDATORY2. CHECK GRADES!!! Final course grades will not be submitted for students who do not check out of lab. This must be done under the supervision of your TA or the Lab Assistant in charge. GOOD LUCK!! General Information There will be a total of ten (10) lecture demonstrations and ten (10) comprehensive quiz-exams. If you have not prepared for (i.e. read and thought about) the lab, you may be "
asked"
to leave and not be permitted to begin or continue the experiment until your teaching assistant is satisfied that you are prepared. You will not be permitted to take a make-up for that experiment. Basically, you should know how and why each operation that you will be doing that day is done. If you do not know, you should see your instructor BEFORE coming to the laboratory. Two experiments will require Formal reports. Guidelines will be set by the T.A. Safety goggles MUST be worn at all times in the laboratory. Wash your hands EVERY time you leave the laboratory. Do not eat, drink, or smoke in the laboratory. A neat work area is the key to a successful experiment. Keep your glassware clean. Wash all glassware immediately after use. DO NOT take reagent containers to your work area. DO NOT put water insoluble materials into the sinks. DO NOT put broken thermometers or mercury in the waste containers. (Notify your TA of a broken thermometer immediately!!!) Please report on the form provided or communicate orally to your instructor the following: a) Any accident. b) Any malfunction of equipment. c) Any chemical spills, especially mercury.d) Any broken glassware. All excess reagents and chemicals must be disposed of according to the instructions given in the text. If in doubt, please consult your TA. Students are expected to conduct themselves in a professional manner during the lab. Students who want to contest a grade must do so to their lab TA within two (2) days of receiving graded quiz or lab report. Please note the following: Each student should confine his/her activities to the workstation, the hoods (dispensing, disposal areas), and areas designated for determining melting points and weighing stations. Playing around (physical contact, loud conversations with other students), squirting chemicals or playing with ice, etc. will not be tolerated. The TA in charge has the authority to dismiss you from lab, and in turn you will then receive a zero for that assignment. All electronic devices are to be turned off during lab. There will be no text messaging, cell phones, iPods, etc. during the scheduled lab meetings. The organic labs are very crowded. You must therefore move calmly and cautiously when you need to obtain chemicals, equipment, and other items necessary for your experiment. Do not disturb other students by having loud conversations and joking across the room. You must carry out your experiment without disturbing others around you. It is not advisable to do the lab if you are on any type of medication that causes drowsiness. Ex: Medications prescribed for allergies, etc. If you are on medication, you should talk with your TA about rescheduling the lab. You must be alert during the lab. No visitors are permitted in the lab during lab time. Make-up LabsIf you are going to miss a lab you must notify your TA and have a valid University excuse. If a lab is missed the TA will assign a project to count for the missed lab. Note: A student will not be permitted to participate in an experiment unless he/she has attended the lab lecture. Handouts and other relevant material may be given out immediately before the lab lecture and will not be available afterward. Post-Laboratory Reports These reports should include your results, data, observations, calculations, conclusion and spectral analysis. Failure to follow these instructions will result in the unnecessary loss of points!!! A final grade will not be assigned unless all reports are turned in. Check-in / Check-out ProcedureAll students taking 333L are required to formally check-in on the first day of classes. All items of glassware, on the list provided, should be carefully and thoroughly checked. Look for cracks, chips, etc. Also check the thermometer provided and make sure it reads up to at least 250º C. Any missing items or concerns should be attended to during check-in ONLY!!! You will not be provided replacements for missing or broken items after the first week of class. A = 90% and aboveB+ = 85% - 89%B = 80% - 84%C = 70% - 79%Note: This grading scale is subject to change.Any questions pertaining to the assignment of grades should be clarified at the end of the course and NOT after the grades are posted.At the end of the semester each student will be required to check-out on the assigned date and time, making sure that ALL items are clean and in good condition. You will not be assigned Final Grades until your TA has officially checked you out of the laboratory. GradingSafety Quiz= 100 points10 Experiments = 1000 pointsFinal Exam = 200 pointsTotal= 1300 points These rules will be strictly enforced!!! Academic ResponsibilityFaculty and students at USC are obliged to follow the USC Code of Academic Responsibility. I expect all class members to demonstrate intellectual honesty and to respect the academic rights of their classmates. If you have forgotten your responsibilities under this Code, please re-read Student Affairs Policy STAF 6.25 on USC's web page. Grading Rubric for Chem 333L/334L The grading for the lab will follow the syllabus and is broken down below: Each lab is worth 100 pts total:25 pts Quiz 25 pts Prelab 50 pts. Postlab The quizzes will vary for each TA as each lecture will slightly vary. Each quiz, however, will be worth a total of 25 pts. The lab reports will be worth a total of 75 pts and are broken down below. Prelab (25 pts) Formatting (3 pts) All font 12 pt. Times New Roman (unless otherwise specified) 1 ‘’ margins on all sides Paragraphs are single spaced with an additional line between paragraphs Section Titles are 12 pt. Font Bold Figure captions and Table captions are to be 10 pt. Font Labs are to be written in 3rd person narrative Any additional preferences will be discussed by TA Title Page, style of writing, etc. Objectives (2 pts) Must be stated and written in paragraph format The student should discuss what is to be achieved experimentally The student should discuss what is to be gained intellectually. Any additional preferences will be discussed by TA Intro/Theory (5 pts) Consists of no more than 5 paragraphs Contain at least one literature citation Should not be copied directly from the lab manual, however the lab manual may be used as a guide to writing the theory Questions to consider answering in section include Why does this experiment work? What are the driving forces? What procedures and techniques aid in this experiment? How is this applied in the real world? Any additional preferences will be discussed by TA Mechanism (2 pts) Self Explanatory Must use proper arrow pushing Should not be copied and pasted from lab manual Any additional preferences will be discussed by TA Procedure (1 pts) Should be written in own words Any additional preferences will be discussed by TA Apparatus (2 pts) Should be labeled properly Any additional preferences will be discussed by TA Reagent Table (8 pts) Table cannot be copied and placed directly into report. Must be self produced. Any additional preferences will be discussed by TA Disposal (1 pt) Self explanatory Any additional preferences will be discussed by TA References (1 pt) Self explanatory Any additional preferences will be discussed by TA Postlab (50 pts) Formatting (4 pts) All font 12 pt. Times New Roman (unless otherwise specified) 1 ‘’ margins on all sides Paragraphs are single spaced with an additional line between paragraphs Section Titles are 12 pt. Font Bold Figure captions and Table captions are to be 10 pt. Font Labs are to be written in 3rd person narrative Any additional preferences will be discussed by TA Title Page, style of writing, etc. Results (20 pts) Observations Melting Point % Yield Any other data collected Calculations Summarized with narrative Any additional preferences will be discussed by TA Conclusions (20 pts) Summary of experiment Identify what has been learned What has been proven? Any additional preferences will be discussed by TA Analysis of IR/NMR (5 pts) IR/NMR results must be included in lab Peaks must be labeled properly IR/NMR must be discussed in results or conclusions section Any additional preferences will be discussed by TA References (1 pt) *Note: Any additional materials that need to be submitted for a particular experiment will be discussed by the TA if necessary. Any adjustments made to the grading rubric will also be discussed by TA if necessary.