Introduction to Organic Chemistry Laboratory ~ CHM 126 (Laboratory for Chemistry 124) Course Information and Syllabus ~ Summer Session I, 2007 Course Instructors Laboratory Director Cindy Graham Brittain, PhD; cbrittain@chm.uri.edu Office: Pastore 215B; Phone: 874-2028 Teaching Assistants Jinfang Wu; jinfangwu@mail.uri.edu Da Xiao; xd422@hotmail.com Laboratory Materials • • • • • • • RAM account and card to purchase items through the stockroom (NO CASH will be accepted) Safety goggle or glasses, available in stockroom ($6.00-$8.00) Lab coat, available in stockroom ($17.00) Protective gloves for ALL wet labs (MUST be purple nitrile gloves), available in stockroom ($0.25 per pair) Bound laboratory notebook with carbonless copy paper, available at campus bookstore For some experiments, a scientific calculator Experimental handouts (available at CHM 126 Course Web Page: http://www.chm.uri.edu/chm126/index.html Laboratory students are expected to carefully study (and will be held accountable for) all CHM 126 documents posted for their use on this website or provided by an instructor in lab. Attendance CHM 126 is a laboratory course requiring hands-on experimentation and direct observation of physical and chemical changes. For this reason, students must be present to conduct each experiment. Attendance is REQUIRED at the day and time for which each student has registered. (As discussed below, each student will be permitted ONE absence without penalty. Only under exceptional and fully documented circumstances will Dr. Brittain permit a second unpenalized absence. Any student who is absent from more than two experiments will automatically receive a failing grade in the course.) THERE WILL BE NO OPPORTUNITY TO MAKE-UP A MISSED EXPERIMENT; students should not inquire about make-up experiments. Due to safety considerations, under NO circumstances will students be permitted to attend a laboratory section other than the one for which they have officially registered. Schedule of Experiments Date M 5/21 T 5/22 W 5/23 T 5/29 W 5/30 M 6/4 T 6/5 W 6/6 M 6/11 T 6/12 W 6/13 M 6/18 Experiment Course Information, Check-in to Drawers, Mandatory Dry Lab 1: Laboratory Safety (Report Sheet) Dry Lab 2: Organic Compounds (Quiz, Lab Notebook—see exception below, Report Sheet) Wet Lab 1: Purification of Acetanilide by Recrystallization (Quiz, Lab Notebook, Report Sheet) Wet Lab 2: Separation of Liquids by Distillation (Quiz, Lab Notebook, Report Sheet) Wet Lab 3: Separation of Spinach Pigments by TLC (Quiz, Lab Notebook, Report Sheet) Wet Lab 4: Synthesis of Cyclohexene by Dehydration of Cyclohexanol (Quiz, Lab Notebook, Report Sheet) Wet Lab 5: Synthesis of Aspirin (Quiz, Lab Notebook, Report Sheet) Wet Lab 6: Synthesis of Nylon (Polyamide) (Quiz, Lab Notebook, Report Sheet) Wet Lab 7: Organic Functional Group Analysis (Quiz, Lab Notebook, Report Sheet) Wet Lab 8: Preparation of Esters and Soap (Quiz, Lab Notebook, Report Sheet) Wet Lab 9: Characterization of Carbohydrates (Quiz, Lab Notebook, Report Sheet) Final Exam, Course/TA Evaluation, Check-out of Equipment Drawers Grading Policy The course grade will be based on the following: 9 Pre-Lab Quizzes (20 points each) 9 Lab Notebook Assignments (20 points each) 9 Lab Performance Assessments (10 points each) 10 Report Sheets (50 points each) Laboratory Final Exam 180 points 180 points 90 points 500 points 150 points 1100 points Note that students have the opportunity to earn 100 points at 10 of the 12 lab meetings: 50 points for the Report Sheet, 20 points for the Pre-Lab Quiz, 20 points for the Lab Notebook, and 10 points for the Lab Performance Assessment. The mandatory Dry Lab 1: Laboratory Safety provides an additional 50 points, and the Laboratory Final Exam makes up the remainder of the grade. Pre-Lab Quizzes: All laboratory activities (except Dry Lab 1: Laboratory Safety) will require a Pre-Lab Quiz to demonstrate that students have effectively prepared to conduct the experiment. 10 quizzes will be given; the lowest quiz grade will be dropped. Information about the Pre-Lab Quizzes is provided in the attached “Remedies” document. Note that these quizzes will be given promptly at the beginning of each lab meeting, and students who arrive late (after the quiz has been completed) will receive a zero for that day’s quiz. Lab Notebook: All laboratory activities (except Dry Lab 1: Laboratory Safety) will require documentation in the Lab Notebook. The lowest Notebook grade will be dropped. Guidelines for preparing the Lab Notebook Assignments are provided in the attached “Remedies” document. Note that the “Remedies” document specifies that Sections I and II of the Lab Notebook assignment MUST BE COMPLETED IN ADVANCE as preparation for conducting the experiment. Teaching Assistants will examine, sign, and date the initial Lab Notebook entries, and students who have not completed this pre-lab assignment will not be permitted to work in the laboratory (and will receive a zero for that day’s experiment). (Dry Lab 2: Organic Molecules is the single exception to this pre-lab work rule. Preparatory work in the Lab Notebook is not required for this dry lab; however, students must bring their notebooks to the laboratory that day and work the exercise in their notebooks, rather than on the Report Sheet.) Report Sheets: A Report Sheet is required for each of the 11 laboratory activities (2 “Dry” Labs, 9 “Wet” Labs). The lowest Report Sheet grade will be dropped. Guidelines for completing the Report Sheet are provided in the attached “Remedies” document. For ALL experiments: The Report Sheet should be completed only after the experiment has been finished and all data/results have been worked out in the Lab Notebook. The Report Sheet is due at the next meeting of the lab section, and this work should be ready to turn in promptly at the start of that next meeting, along with the carbon copies of all relevant pages from the Lab Notebook. Lab Performance Assessment: During each experiment, the teaching assistant will objectively assess each student’s performance in the lab, and award up to ten points for appropriate laboratory behavior and technique. These points are earned by: demonstrating familiarity with the experimental procedure, demonstrating proper experimental technique, properly using the lab notebook to record data/observations (rather than Report Sheets), keeping personal lab bench and communal areas clean, properly (and carefully) disposing of waste, interacting appropriately with fellow students and the teaching assistant, and adhering to safety regulations. Students who remove their safety glasses during an experiment and must be reminded by the teaching assistant to replace them will immediately lose five points from the lab performance point total awarded for that experiment. Students will work in pairs on each experiment. If a lab section has an odd number of students, one work group may contain three students. No group may have more than three students working together at one time. Additional Note on Attendance: As discussed above, if a student is absent from ONE laboratory meeting, the Pre-Lab Quiz, Lab Notebook assignment, and Report Sheet grades for that meeting will be zero, but these scores will be dropped. A second laboratory absence will result in grades of zero, and these scores will NOT be dropped. Dr. Brittain may permit a second unpenalized absence, but only if the circumstances of the absence can be fully explained and documented. Any student who is absent from more than two laboratory meetings will automatically receive a failing grade in the course. Active participation in the experimentation is required to receive credit for this course. Students should be aware that ALL of the laboratory experiments will be represented on the Final Exam, and students who have missed an experiment are likely to be at a significant disadvantage. Laboratory Final Exam: The Final Exam is mandatory, and it is comprehensive. Any student who must miss the final exam should contact Dr. Brittain immediately and provide documentation that clearly outlines the need for a make-up exam. A Laboratory Skills Summary will be provided to assist students in studying for the Final Exam. Laboratory Safety Nothing is more important than the personal safety of the occupants of the laboratory. For this reason, any student who deliberately or carelessly disregards a written or oral safety instruction will be immediately expelled from the laboratory and will receive a grade of zero for the experiment. A student who is expelled twice from the laboratory for safety violations will automatically receive a failing grade in the course. Careless disregard of safety instruction includes: 1. Any student who has not completed Sections I and II of the Lab Notebook Assignment so as to demonstrate effective preparation for the experiment. 2. Any student who improperly disposes of chemical waste (pours solutions into laboratory sinks, or places solid waste into a garbage can). 3. Any student who does not have the following personal protection items: • • • • Safety glasses or goggles Lab coat (clothing which covers the arms to below the elbow and legs to below the knee) Protective gloves Shoes which fully enclose the foot (no open toe or heel). Socks must also be worn. Students who forget to bring their personal protection items will face a costly penalty: The chemistry stockroom will provide a disposable lab coat for one-time use ($3.00) to students who forget their lab coats. Protective booties are provided ($0.90) for students with inappropriate footwear. Chemistry department personnel are prohibited from loaning safety glasses or goggles by State of Rhode Island health/hygiene regulations; students who forget their safety glasses should not inquire about loaner eyewear, and must plan on purchasing a replacement pair of safety glasses at full cost. Academic Honesty Although students are conducting each experiment in groups of two or three, each student’s Lab Notebook Assignment and Report Sheet must be completed on an individual basis. Students who submit work that is clearly the same as another student’s work are in violation of the University’s Policy on Academic Honesty; those students will be held accountable as described in that Policy. Academic dishonesty is considered a serious offense, and disciplinary action will be taken immediately. The university’s policy on academic honesty is detailed in the student handbook (available online). That policy is summarized below: Students are expected to be honest in all academic work. A student’s name on any written work, including assignments, lab reports, internship reports, papers, or examinations, shall be regarded as assurance that the work is the result of the student’s own thought and study. Work should be stated in the student’s own words, and produced without assistance or properly attributed to its source. When students are authorized to work jointly, group effort must be indicated on the work submitted. The following are examples of academic dishonesty: • Unauthorized communication during exams. • Unauthorized use of another’s work or preparing work for another student. • Taking an exam for another student. • Altering or attempting to alter grades. • The use of notes or electronic devices such as calculators, computers, or cell phones to gain an unauthorized advantage during exams. • Fabricating or falsifying facts, data, or references. • Facilitating or aiding another’s academic dishonesty. When there is an allegation of academic dishonesty, the instructor may: • Fail the student for the assignment. • Recommend that the student fail the course.