CHEM 2123L: ORGANIC CHEMISTRY I LAB Fall 2017 Instructor: Jose L. Ontiveros, Jr. Office Mailbox: STC 318 Office Hours: Wednesdays and Thursdays 1:00 pm 2:00 pm, STC 301 or by appointment Email: jontiveros2@leomail.tamuc.edu Lab Section 03: Wednesday 2:00 pm 5:50 pm, STC 308 COURSE INFORMATION Text/Manual and other required material: Lab Manual: Introduction to Organic Laboratory Techniques: A Small-Scale Approach, Fourth Edition. Pavia/Lampman/Kriz/Engel, 2016, ISBN-13: 978-1-30525392-6 Supplies to be purchased before the first lab meeting: ANSI certified safety glasses, two combination locks per group, and appropriate lab attire, lab coats (highly recommended but optional), bound notebook (carbon copy - optional) Course Description: Introduction of techniques for organic chemistry laboratory, including preparation, setup, and running reactions and the characterization of the properties of representative organic compounds. Student Learning Outcomes/Course Objectives: By the end of the semester I intend for my students to have realized a number of objectives. 1. Learn basic synthetic organic chemistry techniques: how to set up reactions, how to monitor the progress of a reaction, how to calculate the amount of starting materials needed, how to calculate percent yields, and how to properly clean glassware at the end of an experiment. 2. Learn basic techniques for the isolation and purification of organic molecules: distillation, recrystallization, chromatography (TLC and column), and extraction. 3. Learn how to characterize organic compounds using techniques and instrumentation: melting point, boiling point, retention factor, 1 H-NMR, 13 C-NMR, IR, and UV/Vis spectroscopy. 4. Learn the safety requirements and methods needed to work in an organic chemistry laboratory. 5. Learn how to safely handle, utilize and dispose of chemicals. 6. Learn how to document laboratory experiments, maintain a scientific notebook. 7. Know the importance of organic chemistry and its relationship to various other disciplines such as biochemistry and medicinal chemistry and our daily lives. GRADING Your laboratory grade will be based on eight of your best experimental write-ups, and a spectroscopy packet containing IR, 1 H-NMR, and 13 C-NMR data for six organic compounds. Write-ups (notebook and write-up): 80% Spectroscopy problems: 20% 100% Page 1
You are required to submit all laboratory write-ups in a timely manner via email. You will incur a 10% penalty (-6 points) for every day that your lab write-up is late; thus, if a lab write-up is more than 6 days late, you will receive a zero for that report. There will be absolutely no makeups for laboratory experiments. If you miss a laboratory experiment, it will count as your dropped laboratory write-up. If you miss more than one laboratory experiment, you will be assigned a grade of zero for that assignment. See the following website for more details about course withdrawal deadlines: Academic Calendar. Grading will be based on a standard percentage scale: 59-below = F; 69-60 = D; 79-70 = C; 89-80 = B; 100-90 = A. Dishonest scholarship will earn an automatic zero (0) and initiate prosecution to the fullest extent. Incomplete grades may be given only if the student has a current average 70% and is precluded from completion of the course by a documented illness or family crisis. Lab Cleanliness: You will be expected to maintain a clean and orderly lab. At the end of every experiment, your bench space and fume hood must be cleaned. Any equipment utilized during the experiment must be cleaned as well (balances etc.). You should ensure that sinks and floors are also clean. If the lab space and equipment that you utilized during the experiment is left dirty and unorganized, you will be penalized 10% on your lab write-up associated with that experiment. Students are required to report all spills and broken glassware to the instructor immediately. COMMUNICATION AND SUPPORT Communication: If the instructor needs to contact an individual student, it will be via the student s e- mail account on file. Students should check e-mail frequently, especially after absence. E-mail is the best, easiest and fastest way to communicate with me. LABORATORY NOTEBOOK AND POST-LAB GRADING RUBRIC Laboratory Notebooks: You must write down what you observe and take measurements during the time of the experiment. Compose the laboratory notebook in sufficient detail to allow someone else to repeat the experiment exactly. You will not be allowed to use your lab textbook while in lab due to time constraints. The observations section of the report must be the original notes taken during the course of the experiment (take detailed, legible notes during the experiment). You may type and paste the reagent and stoichiometry tables into your laboratory notebook. However, you MUST submit your original notes taken during the experiment. Each laboratory report will consist of the following sections: 1. Laboratory Notebook 40 points (Pre-lab due at the beginning of the laboratory) o Title 1 point 1. Example: Exp. 1 Title of experiment o Physical Constants/Reagent Data Table 10 points 1. Make a table(s) to clearly list the chemical and physical properties of all the solvents and chemicals you will use. a) The properties include but are not limited to: amount in grams and/or ml (depends on physical state), molecular weight, density, moles, equivalence Page 2
(eq.), melting point (m.p.), boiling point (b.p.), actual yield, theoretical yield, percent yield, color, phase, flammability, toxicity and safety notes. o Stoichiometry/Theory 5 points 1. Chemical Reaction 2 points (goes before reagent table) 2. How much of each reactant should be used 1 point (listed within the reagent table) 3. What s the theoretical yield by calculation 2 points (list value in table) o Safety 5 points 1. Read the special instruction part carefully so that you won t be injured. 2. How to deal with the dangerous chemicals and operations should be listed clearly. o Procedure and Observations 15 points 1. Itemized and step by step (Don t copy the text book directly) 2. You are encouraged to explain the key steps after the particular procedures 3. Observations ( T chart Procedure on the left, Observations on the right or viceversa) a. List the phenomenon you have observed such as bubbles formed, the color of the mixture changed from colorless to rose, two layers were formed from one phase, green crystals formed o Student Signature and Experiment Completion Date 1 point 1. Standard procedure and authenticates your work o Instructor s Initials 3 points 1. Notebook was completed as prescribed by instructor 2. Proof that you actually completed the lab and not counted absent 3. Hood/bench area are clean and all glassware has been put away 2. Post-Laboratory Write-up 60 points (due by the beginning of the next laboratory period) o Observations 15 point 1. Once the experiment has been performed, transcribe your observations into complete sentences. Be sure to include details pertaining to the instruments, equipment, glassware, reagents amounts, techniques, time durations and physical appearances that you observed during the reaction. o Results 15 points 1. Show calculations for determining the limiting reagent, theoretical yield, percent yield 2. Report melting point range. 3. Attach your labeled experimental NMR/IR and literature handouts. o Discussion 15 points 1. Discuss why your results were what they were using the concepts presented in the lab manual and lecture textbook. a) Thiamine catalysis and factors that affect the reaction b) Explain the mechanism c) Compare your experimental proton NMR data to the literature handout. (i.e. This means what chemical shifts are present and/or absent in your experimental NMR.) 2. Report all sources of error that justify your percent yield, experimental NMR impurities and melting point range. a) Identify the problem b) Come up with a solution to fix the problem. Page 3
c) What effect does this solution have on your percent yield, experimental NMR impurities and melting point range? o Questions 15 points 1. Answer the assigned problems according to the syllabus in complete sentences.* COURSE AND UNIVERSITY POLICIES Class Attendance Policy: All students are expected to attend classes on a regular basis and attendance will be recorded. The Department of Chemistry adheres to the attendance policy set by the University as stated in the most current Undergraduate Catalog. Being late by more than 5 minutes is equivalent to missing a laboratory. You must be on time in order to take a quiz or an exam. Excessive absence is defined as missing more than 10% of the laboratory sessions without excusable reasons. Excessive absence will be reported to the Dean of the College and the Dean of Students. In addition, according to the TAMU-Commerce Procedure A13.02., good class attendance will be necessary in order to pass the course. Student Conduct Policy: All students enrolled at the University shall follow the tenets of common decency and acceptable behavior conducive to a positive learning environment (see Student s Guidebook, Policies and Procedures, Conduct). Any student engaging in disruptive behavior will be dismissed from class on the first offense. A second offense may constitute dismissal from the course. Nondiscrimination Statement: Texas A&M University-Commerce will comply in the classroom, and in online courses, with all federal and state laws prohibiting discrimination and related retaliation on the basis of race, color, religion, sex, national origin, disability, age, genetic information or veteran status. Further, an environment free from discrimination on the basis of sexual orientation, gender identity expression will be maintained. Academic Integrity and Dishonesty Policy*: Academic cheating, plagiarism, and other forms of academic misconduct may result in removal of the student from class with a failing grade or may in extreme cases result in suspension or expulsion from the University as described in the Code of Student Conduct section of the Student1s Guidebook A&M-Commerce Procedure 13.99.99.R0.10. ADA Statement: The Americans with Disabilities Act (ADA) is a federal anti-discrimination statute that provides comprehensive civil rights protection for persons with disabilities. Among other things, this legislation requires that all students with disabilities be guaranteed a learning environment that provides for reasonable accommodation of their disabilities. If you have a disability requiring an accommodation, please contact: Office of Student Disability Resources and Services Texas A&M University-Commerce Gee Library- Room 162 Phone (903) 886-5150 or (903) 886-5835 Fax (903) 468-8148 or Email: StudentDisabilityServices@tamuc.edu TENTATIVE LABORATORY SCHEDULE OF EXPERIMENTS Week Chapter/Topic Dates Experiments & Assigned Problems 1 First Week of Classes 08/30 Syllabus, safety lecture, exam, notebooks, write-ups, check-out Page 4
2 Experiment 1 Solubility 09/06 Read Experiment 1 (pg. 2) and required techniques (5, 10). Write-up the experiment for Parts A-D as prescribed on page 6 and 7. 3 Experiment 2 Crystallization 09/13 Read Experiment 2ABC and the required techniques (8-11). Write the report up as described on pages 16-17, answer questions 1-3 in the report. 4 Experiment 3 Extraction 09/20 Read Experiment 3A and the required techniques (10, 12). Answer questions 1 and 2 (pg. 25) in the report. 5 Experiment 15 Isolation of Chlorophyll and Carotenoid Pigments from Spinach 09/27 Read Experiment 15 and the required techniques (5-7, 12, 19, 20). Read the essay on pages 104-10: Chemistry of Vision. Obtain R f values for each component. Answer questions 1-4 in the report. 6 Experiment 20A Competing Nucleophiles with 1- butanol or 2-butanol 10/4 Read Experiment 20A and the required techniques (1-7, 12, 22, 26). 7 Experiment 20B & 20C Competing Nucleophilic with 2- methyl-2-propanol 10/11 Read Experiment 20B and 20C and the required techniques (1-7, 12, 22, 26). Answer questions 1-5 in your report. I will hand out your spectroscopy packet during this lab period. 8 Chapter 12 10/18 9 Chapter 13 10/25 No experiments this week. Dr. Headley will lecture over Infrared Spectroscopy (technique 25) and Mass Spectrometry, (technique 28). No experiments this week. Dr. Headley will lecture over Proton and Carbon NMR spectroscopy (techniques 26 and 27). One lab member from each group needs to come in and set up Experiment 27A. 10 Experiment 27A Chiral Reduction of Ethyl Acetoacetate 11/1 Read Experiment 27A and the required techniques (22). Read the essay on page 218: Green Chemistry Include your labeled IR spectrum in your write-up. ACS SWRM and Pathways Week 11 Experiment 47 Benzocaine 11/8 Read Experiment 47 and the required techniques (22-23). Read the essay on page 354: Local Anesthetics, Answer questions 1-5 and include an H-NMR spectrum in your report. 12 Experiment 33A Triphenylmethanol 11/15 Read Experiment 33A and answer questions 1-5 in your writeup. Drawer check-in and Spectroscopy packets are due. Note: The instructor reserves the right to make any changes to the syllabus. Page 5