CHEM304L: Organic Chemistry Techniques I Summer 200 Instructor: Dr. Anja Rosengarth Hours: TTh 8:30 am 2:30 pm and :30 pm 5:30 pm (2 laboratory periods) (Building 7, Room SCI 7) Office hours: I will be available Mondays, Wednesdays and Fridays between 8:30 am and 2:30 pm. Email for an appointment to anja.rosengarth@vanguard.edu Text: ) A Small Scale Approach to Organic Chemistry Techniques, by D. Pavia et al, Third Edition, Cengage Learning, 20) 2) Duplicate Laboratory Notebook, (Hayden McNeil, 20) Catalog Description: CHEM 304L Organic Chemistry Techniques I ( unit) Prerequisites: CHEM20/2 and CHEM20L/2L Co-requisite: CHEM304 This is the complementary laboratory course for CHEM304. This course is designed to develop basic skills and techniques for practical application of the general principles of organic chemistry. The development of a safe approach to lab experimentation will be stressed. Four four-hour laboratory sessions per week (for Summer 200 changed by Instructor). Lab fee. Student Outcome: The main objective of this course is to expand the chemical principles and concepts that were introduced in CHEM 20/L and CHEM2/L (General Chemistry I and II) and to introduce new experimental techniques that involve organic synthesis. Student confidence in the laboratory is of primary concern and confidence is best obtained by competence in technique and mastery of theory. Proper data treatment and calculations will be stressed. Course format: Before class: ) Every student has to do an online quiz related to the experiments scheduled for that particular day before coming to class. If the student is not able answer 80% of the quiz correctly, he/she will not be allowed in the laboratory to conduct the experiment related to the quiz. Since most of the time two experiments will be scheduled for one day (one for the session, one for the session), two quizzes are required. One quiz will be dropped from the grade calculation. 2) Every student needs to do the assigned reading for the scheduled experiment(s). 3) A pre-laboratory report for the scheduled experiment is due before the start of the experiment. This prelaboratory report is comprised of a) the main title/objective of the experiment, b) a main reaction (or separation scheme if applicable), and c) any pertinent physical constants. If this pre-laboratory report is not available, the student gets 0 minutes to get it done. If it is not done within 0 minutes, the student will have to leave the lab and is not permitted to work on the scheduled experiment which will result in 0 points for the experiment. One pre-laboratory report will be dropped from the grade calculation. The beginning of the class: The beginning of the class will be devoted to a small lecture covering the experiment scheduled and the background theory. Safety issues and proper waste disposal will also be discussed. The majority of the time will be taken by the experiment itself and the evaluation of the data. The experiments will NOT be conducted in pairs. Every student is responsible for his/her own experiment. It is imperative that students do not show up late because of the tight schedule. Any student showing up more than 0 minutes into the laboratory
period automatically receives a zero and an absence for that laboratory exercise. Any student showing up unprepared for the experiment, either in dress or in the completeness of the pre-laboratory report, has until the end of that 0 minute period to rectify the matter, after which the student will receive a zero for the exercise (see above). VANGUARD UNIVERSITY EDUCATIONAL TARGETS AND GOALS APPLIED TO CHEMISTRY: Educational Targets Intellectual Engagement Professional excellence Responsible stewardship Student Learning Outcomes Activities Assessments. Be able to interpret scientific data. 2. Become proficient with determining reaction products. 3. Become familiar with common organic reactions. 4. Understand organic chemistry as it pertains to life processes. 5. Determine molecular weight and molecular formula from a line structure. 6. Calculate theoretical and percent yield for reactions. 7. Obtain basic understanding of processes occurring during lab experiments (carrying out reactions, washing, drying, extraction, heating at reflux, etc.). 8. Properly interconvert between mass and volume of reagents by the use of density. 9. Determine the weight and moles of solute in solutions given the concentration as molarity or weight percent along with density. 0. Prepare lab reports that effectively communicate the experiment that was performed.. Develop independent thought processes.. Master basic data manipulations. 2. Know how to present scientific information and data in a formal manner to lay persons. 3. Learn aspects of project management. 4. Master writing chemical equations and formulas. 5. Safely perform the laboratory experiments (read reagent labels, follow procedures). 6. Accurately measure reagents and products used/prepared in chemical experiments (use of balance, melting point apparatus, separatory funnel, etc.). 7. Properly identify and use laboratory glassware (distillation, extraction, drying, etc.). 8. Develop good laboratory safety practices (waste disposal, wearing of gloves and eye protection, safe attire). 9. Accurately measure melting and boiling points. 0. Make efficient use of time.. Be able to explain several environmental issues and its impacts on society. 2. Understand various safety issues in the chemical laboratory. 3. Practice safe laboratory technique in the chemical laboratory. Experimentation Laboratory Notebook Pre-lab lecture Online Quizzes Laboratory Skills & Participation Laboratory Skills & Participation Website: The class has an online companion website through the University s Moodle system where you can find information about the course, lecture notes, homework assignments, and miscellaneous help material. The website is: http://learn.vanguard.edu. Some labs and all quizzes will be posted there. Course Points: The final grade for the CHEM304L class will be comprised of quizzes (5 points each), one special assignment (0 points), pre-laboratory reports (5 points each), complete laboratory reports (30 points each) and technical skills (50 points). You may drop one quiz (but NOT the one related to safety), one pre-laboratory worksheet and one laboratory work sheet. No make-up classes will be available. Missing three laboratory classes will result in the failure of the class (grade F). 2
The maximum of points for each assignment type you can receive in this class are summarized as follows: 35 Quizzes (9 @ 5 points each) equals 27% of final grade 0 Special assignment (0 points) equals 2% of final grade 40 Pre-laboratory reports (8 @ 5 points each) equals 8% of final grade 270 Complete Laboratory reports (9 @ 30 points each) equals 53% of final grade 50 Skills ( @ 50 points each) equals 0% of final grade 505 Total Grading Scale: The following grading scale will determine your final grade: 00 93% A 92 90% A- 89 87% B+ 86 83% B 82 80% B- 79 78% C+ 77 73% C 72 70% C- 69 68% D+ 67 63% D 62 60% D- < 60% F Laboratory Report: As a scientist (biologist, chemist or engineer) being able to effectively record your experimental results and observations is essential to your success. In addition, effectively communicating these results to your peers is critical. As such, laboratory reports constitute the largest portion of your grade for this course. The format for your lab reports must follow the guidelines provided below and will be graded based on the assigned point distribution each lab report will be evaluated on a 30 point scale. General format: A (semi-)formal report will be required for each experiment performed. Reports should be written directly into your lab notebook. The carbon copy will be collected and graded; you must ensure that the carbon copy is legible. (Felt-tip pens don t work; ballpoint pens do work). The reports will be graded on grammar, spelling and content, and should be written using third person, past tense. (I boiled the solution is incorrect. The solution was boiled is correct.) Very frequent spelling errors such as separate, yield, weight and precipitate will always be checked. Each experiment must have a title and be dated. All entries must be written in ink and have the following sections: Introduction/Main reaction, Table of physical constants (including Molecular weight), Separation scheme (most experiments), Data & Observations (What did you actually do?), Calculations (Theoretical yield and percentage yield or weight percentage recovery), Recorded Data (Spectra, melting point, optical rotation, etc.), Summary & Conclusions, Safety & Laboratory Hygiene, and Post-Lab Questions related to the experiment from the book (see A small scale approach to organic laboratory techniques, pp 563-57). Introduction/Main reaction (2 points): A brief statement of what the experiment is about. What will you prepare and how will you prove the identity and purity of the product. Always include the main reaction. Table of physical constants (2 points): Include all published physical constants of your reactants and products. The molecular weights, densities, and boiling/melting points need to be put here. Separation scheme (2 points): A complete work-up or separation scheme of the product needs to be included. Data & Observations (5 points): This section contains a description of what you actually did in your experiment and what you observed. It should be written using third person, past tense (see above). All data (melting points, boiling points, weights, etc) taken during the course of performing the experiment should also appear in this section. 3
Calculations (4 points): Any calculations should be included here. When reactions have been performed, theoretical and percent yields should ALWAYS be calculated. When melting or boiling points have been determined a % difference should be calculated to provide evidence of purity. Be sure to use the appropriate units and significant figures when reporting your data. In addition, all data should be recorded directly into your laboratory notebook not on to scratch paper and then copied into the notebook at some later date. Recorded data (3 points): Recorded spectra and/or optical rotation data need to be attached. The spectra must have your name, sample source, phase and/or solvent written on it. Summary & Conclusions (7 pts): This is the most important section of the report. You should discuss your actual experimental results (i.e melting point, boiling point, product purity, etc). Be sure to include a % Difference if your results differ from the literature values of the mp, bp, etc. Event though you have included this calculation in the Calculations section, it must be included in your Summary. In addition, any % yields must also be reported here. Questions such as the following should be answered: Did the results of the experiment match expectation? Why or why not? Could the procedure be improved? How? Suggest possible reasons why any problem you encountered may have occurred and how to avoid the problem in future. For unknowns, please explain how you came to conclude the identity of your unknown. A simple statement of the unknown s identity is NOT SUFFICIENT!! If spectra have been used, the spectra must be annotated. That is, show how the spectra were used to come to your conclusion. Conclusions should be insightful, critical, and substantial. This is the time to show what was learned during the lab session from performing the experiment. However, you must be CONCISE!! While we do not count words, this section should be no more than 250 words. Safety & Laboratory Hygiene (2 pts): Each experiment must be performed safely, and all chemicals must be handled following proper safety and hygiene protocols. This includes proper disposal of all chemical waste generated during the experiments, proper use of appropriate safety equipment (safety glasses, gloves, etc). Post-Lab Questions (3 pts): For most experiments, there will be a standard set of questions. These questions must be completed and turned in with your lab report unless you are informed otherwise. Safety & Lab Policy: A primary concern in any laboratory course is safety, including both instruction in safety and proper monitoring of student work in the laboratory. A second concern is to be certain that laboratory courses are conducted within guidelines set by State and Federal offices relative to the handling of hazardous wastes. It is with these concerns in mind that the following policies apply to all students enrolled in laboratory courses offered by the chemistry department. I. Generally, chemistry laboratories do meet during the first week of class for safety training and/or hazardous waste handling training. The department will not offer safety training at the convenience of individual students. It is the student s responsibility to attend safety training for the course in which the student is enrolled. If a student fails to attend the safety instruction offered during the first week of class and/or fails to pass a quiz dealing with safety issues (if given), the Chemistry department reserves the right to automatically drop or withdraw the student from the laboratory program. II. Since important safety and procedural information is often presented in lectures at the beginning of laboratory sessions, students who arrive at scheduled laboratory sessions after lab lectures have begun may not be allowed to begin the experiment and thus may be considered absent from the laboratory session. The decision to permit a late-arriving student to perform an experiment will be at the discretion of the instructor. III. Procedures involving absences from scheduled laboratory meetings after the first meeting: a) No Make-up experiments will be permitted. b) An automatic zero on the experiment will be received for an absence. The instructor does not make a difference between excused or unexcused. If a student has two unexcused absences during the semester, the highest grade that he/she can receive in the laboratory course is a "C". Three unexcused absences will result in an automatic failure of the laboratory course. 4
c) Students are reminded that CHEM 304 is a pre- or co-requisite for CHEM 304L. If a student decides to withdraw from the lecture course, he/she must also withdraw from the laboratory course. This policy holds true for many course combinations in the department. LABORATORY SKILLS RUBRIC: ). Indicate the student s ability to operate/program scientific equipment (0 pts): Instrument 0 Unacceptable Poor IR Student is so not be careless that operate nor be guided through operate instrument guided in the the operation of instrument might be operation of the the instrument. independently Polarimeter damaged. instrument. but doesn t understand the theory. The student can Student clearly operate the can operate the instrument instrument, independently, perform perform basic calculations analysis, and and explain the understand the theory behind basic principle its operation. underlying operation. 2). Indicate the student s ability to acquire scientific information (0 pts): Method Poor SciFinder Student doesn t Student knows be know how to or where the database prompted through Library/Web where to access can be found but the use of the information. not how to use it. database. Student performs Student performs literature searches appropriate with minimal literature searches interference of independently. professor. 3). Indicate the student s ability to perform the following laboratory operations independently (5 pts): 0 Technique Unacceptable Poor Separation / purification Waste management Laboratory Safety Student is so careless that he/she puts the fellow students, the instructor and him/herself into danger. not compounds nor determine hazard conditions of solvents. not compounds and has difficulty in determining the hazards of the experiment. compounds with prompts, can identify simple hazards but cannot determine a safe course to handling chemicals. compounds with prompts, can identify simple hazards but needs help to dispose of hazards. Student is well versed in separation of compounds, identifying hazards and dealing with hazards appropriately. 4). Indicate the student s ability in the following professional skills area (5 pts): 0 Miscellaneous Unacceptable Poor Project Management Protocol Optimization Laboratory Hygiene not manage a task, is unable to develop his own protocol and never cleans up his/her glassware and/or bench. not manage a task, deals poorly with developing his own protocol, and does not work cleanly and efficiently. manage a task but not his time, deals poorly with developing his own protocol, and does not work efficiently. manage his tasks and time, requires significant assistance in developing his own protocols, and works well within guidelines. Student manage his manages his tasks and time, tasks and time requires well, develops moderate his own assistance in protocols developing his independently, own protocols, and works and works well cleanly and within very efficiently. guidelines. 5
Changes: The instructor reserves the privilege of making necessary changes to this syllabus during the course to improve achievement of student learning objectives. In the event of a change, you will be notified in the lecture session. Academic Honesty: As members of Vanguard University, we commit ourselves to honesty. Honesty in our academic work is vital, and we will not knowingly act in manners that erode integrity. Accordingly, we pledge not to cheat, nor to tolerate cheating, nor to plagiarize the work of others. Acts of dishonesty will be dealt with according to established procedures as described in the Academic catalog. Students w/special Needs: For students with documented medical or psychological disabilities, please contact the Coordinator of Disability Services to request reasonable accommodations. The Coordinator of Disability Services is located in the Counseling Center on the second floor of the Scott Academic Center and can be reached at extension 4489 or by email at beth.lorance@vanguard.edu. For students with a documented learning disability who would like to request appropriate accommodations, please contact Barbi Rouse, the Director of Learning Skills, located upstairs in Scott Academic Center at extension 2540 or by email at brouse@vanguard.edu. TENTATIVE COURSE SCHEDULE FOR CHEM304L Date Topic Exp.# Assigned reading due date (lab report) 06/0, Check-in, Equipment, safety info, N/A Special assignment to be discussed in class. introduction, syllabus, Computer programs Techniques, 2, 4, 29 06/0, The determination of boiling points and On Techniques 3, 9 6/08 melting points of organic compounds Moodle 06/03, Fisher Esterfication On Flavors and Fragrances 6/0 Moodle Techniques Vial Organic Chemistry 06/03, Afternoon Free 06/08, Isolation of essential oils from spices by 57A Terpenes and Phenylpropanoids 6/5 steam distillation Techniques 2, 8, 25 06/08, Competing Nucleophiles with 20B/C Nucleophilic Substitution Reactions: 6/5 2-Methyl-2-Propanol Competing Nucleophiles, Exp. 20A Techniques -6, 7.2, 7.4, 7.8, 2.7, 2.9, 2., 24 06/0, Hydrogenation 23 Fats and oils 6/7 (Methyl Stearate from Methyl Oleate) Technique 06/0, Triphenylmethanol and Benzoic Acid 33A/B Grignard reaction 6/7 Techniques 8,, 2, 25 06/5, Aqueous-based Organozinc Reactions 34 Organometallic reactions 6/22 06/5, 06/7, 06/7, 06/22, Isolation of Caffeine from a Tea bag (sublimation done on 6/7) Techniques 7, 8, 2, 22, 25 B Caffeine 2 Techniques 5, 6, 7.2, 7.0, 9, 2. 2.5, 2.7-2.9, 7 A Green Enantioselesctive Aldol Condensation Reaction 38 Aldol Condensation Techniques 5, 6, 7, 8, 2, 23, 25 4-Methylcyclohexene (Elimination) 22 Elimination mechanisms, Dehydration of an alcohol Techniques 5, 6, 2, 4, 25 Finishing up experiments (example: Sublimation of Caffeine) 6/29 6/24 6/24 N/A Techniques 7 6/24 These techniques are found in the Pavia, et. al. text. There is also an accompanying video on the Cengage website that you ll need to view. Remember all pre-lab quizzes include questions from the techniques and the essays for each experiment. 2 These Essays are found in the Pavia, et. al. text. 6
LABORATORY SAFETY GUIDELINES. Safety equipment: Know the location of the fire extinguishers, safety showers, first aid kit, eye wash equipment, fire blanket. 2. Eye and skin protection: Safety glasses or safety goggles must be worn at all times when lab work is being done. Shoes with tops that shed liquids are required. Clothing should cover the skin from neck to knee and at least to the elbow. Wear gloves when handling corrosive chemicals. Long hair should be tied back. 3. Chemical and heat burns: If you spill chemicals on your skin or clothing, wash immediately with large amounts of water. Get help from other students if needed, notify instructor. For heat burns, apply cold pack (or ice water) to burn and notify instructor. 4. Cut protection: Replace any chipped or broken glassware. In the event of a cut, notify instructor, remove glass, wash wound, use bandaging from first aid kit and apply pressure to slow bleeding, see nurse. 5. Ingestion and inhalation hazards: Never pipet any chemicals by mouth. Eating and drinking in the lab is NOT allowed. Use caution in smelling any chemical. Wave the vapor towards your nose with a fanning motion of your hand. If an experiment generates fumes, move the experiment into the fume hood. 6. Environmental stewardship: Dispose of excess or waste chemicals in special containers in the fume hoods dedicated for waste disposal, using directions given by the lab manual and/or the instructor. Only very dilute aqueous solutions of neutralized chemicals can be washed down the drain with copious amounts of water. 7. Earthquake: Turn of all burners, hot plates, supplies of natural gas. Go to Evacuation Area. 8. Chemical contamination: Always wash hands before leaving the laboratory. Maintain clean lab equipment, immediately clean up all chemical spills and notify instructor, wipe down your lab area before leaving. 9. Fire protection: In the event of a fire, notify instructor immediately. Small fires can be smothered with a watch glass. If a fire extinguisher is used, aim at the base of the flames. Do not discharge a fire extinguisher when a person s clothing is on fire use fire blanket or safety shower. 0. Accident report: Notify instructor no matter how small an accident. LABORATORY PRACTICES. Develop sound lab techniques. Every experiment assigned from the book is accompanied by several technique sections in your textbook. Please make sure you read all of them before coming to class. 2. Never return unused chemicals to the reagent bottles, whether solid or liquid. Discard chemicals properly, or give excess to another student who needs it. 3. Keep balances clean at all times, always use weighing trays or glass containers to weigh a chemical. Clean solid and especially liquid spills on the balances. 4. Do not work in the lab alone, do not do unauthorized experiments. 5. Keep aisles and safety equipment area free of obstructions (backpacks, chairs, etc.) 7