Introductory Physical Science PHSC 102 3 Credits Bea 238 s4

CHEM 327 Intermediate Organic Chemistry Fall 2007

Instructor: Ms. Cindy Lamberty Office: Bea 207 Phone: 985.448.4167 or 448.4502 e-mail: [email protected] Office Hours: 9:30-12:30 MW, 9:00-12:00 T/TH* *some days I will be recruiting off campus

CATALOG DESCRIPTION: CHEM 327. Intermediate Organic Chemistry. 2-1-3. Prerequisite: CHEM 226. Continued laboratory study of the properties, preparation, and analysis of organic compounds. Experimental reports incorporate scholarly organic chemical literature as a primary source. (40.0504)

PREREQUISITES: CHEM 226

REQUIRED TEXTS AND OTHER MATERIALS: 1. Doxsee, K.M. and Hutchinson, J.E. Green Organic Chemistry: Strategies, Tools, and Laboratory Experiments, Thompson Publishing, Brooks/Cole, 2004 2. Safety Goggles—Approved by instructor. 3. The ACS Style Guide; Dodd, J.S., Ed.; American Chemical Society: Washington D.C., 1997. 3. Notebook—bound, duplicating notebook with tear out sheets.

REQUIRED SUPPLEMENTARY READINGS: Organic journal articles as assigned.

COURSE GOALS: The student will develop an understanding of and employ proper techniques used in organic synthesis, data collection, product analysis, and documentation. The student will also develop skills in chemical literature search and critical analysis of relevant chemical literature.

STUDENT OUTCOME OBJECTIVES: At the end of this course the student will be able to  Synthesize various organic compounds  Identify organic compounds using infra-red spectroscopy, thin-layer chromatography, gas chromatography, and nuclear magnetic resonance  Identify organic compounds using traditional wet chemistry techniques.  Prepare scientific reports utilizing chemical journal articles  Discuss critical analyses of chemical journal articles

COURSE CONTENT: 21 August Introduction to Course: EXPECTATIONS Week 1 23 August Check In, Safety and Library Tour 28 August Introduction Week 2 30 August Biodiesel Synthesis and Start Biodiesel of Ethanol from Molasses (Handout) 4 September Identification and Evaluation of Chemical Hazards Week 3 6 September Completion of Biodiesel of Ethanol 11 September Chemical Exposure and Environmental Contamination Week 4 13 September Synthesis and Recrystallization of Adipic Acid (Exp 5) 18 September Sources of Information about Chemical Hazards Week 5 20 September Liquid CO2 Extraction of D-Limonene from Orange Rind (Handout) 25 September Introduction to Green Chemistry Week 6 27 September A Greener Bromination of Stilbene (Exp 3) 2 October Alternative Solvents Week 7 4 October Gas Phase Synthesis, Column Chromatography and Visible Spectroscopy of 5,10,15,20-Tetraphenylporphyrin (Exp 7) Week 8 9 October Midterm 11 October Fall Break, NO CLASS 16 October Alternative Reagents Week 9 18 October Solid Phase Photochemistry (Exp 16) 23 October Reaction Design and Efficiency Week 10 25 October Solventless Aldol (Exp 1) 30 October Alternative Feedstocks and Products Week 11 1 November Complete Photochemistry and Begin Combinatorial Chemistry (Exp 19) 6 November Big Picture and Green Chemistry Metrics Week 12 8 November Complete Combinatorial Chemistry 13 November Summaries Week 13 15 November Summaries 20 November Thanksgiving Break, NO CLASS 22 November Thanksgiving Break, NO CLASS 27 November Check-out and Review Week 14 29 November Final Exam

COURSE REQUIREMENTS: All students will perform all experiments using proper safety practices. Notebook: 20 points/experiment 5 experiments 100 points Laboratory Reports: 50 points/experiment 5 experiments 250 points Chemical Literature Reviews: 25 points/review 4 reviews 100 points Research Paper 1 paper 100 points Final Exam 60 points

LAB REPORTS: 1. Biodiesel 2. Adipic Acid 3. Greener Bromination 4. Gas and Solid Phase Chemistry 5. Combinatorial Chemistry

RESEARCH PAPER: You will prepare a 3-5 page typed paper based upon one of the winning Presidential Green Chemistry Challenge projects (http://www.epa.gov/greenchemistry/pubs/pgcc/presgcc.html). Instructor must approve the topic before beginning paper.

CHEMICAL LITERATURE REVIEWS: Journal articles related to the Green Chemistry concept and/or the experiments performed will be read and reviewed by students. The review will consist of a one page summary of the article and related articles. Please be sure to turn in a copy of the main article with the summary. Two of the four reviews will be completed by a team of students, the remaining two will be completed individually.

METHOD OF EVALUATION: A straight percentage is used to determine grade. A = 90% B = 80% C = 65% D = 55%

MAKE-UP POLICY: No make-ups are allowed for the experimental or discussion portion of the class. Late laboratory reports or written reviews will be deducted 5 points per day.

ATTENDANCE POLICY: Attendance is mandatory. If you miss one (1) laboratory or one (1) discussion with excused absence I will recalculate grade. Unexcused absences result in a zero for that experiment or discussion. ACADEMIC HONESTY POLICY: Any student found cheating, including plagiarism, will be subject to the penalties as stated in the Student Code of Conduct handbook; including but not limited to a score of zero on exam, review or report, expulsion from the class or expulsion from the University.

SEMESTER WITHDRAWALS : The last day to withdraw from the class with a “W” is 26 October 2007

ACADEMIC DISABILITIES POLICY: If you have a documented disability that requires assistance, you will need to register with the Office of Disability Services for coordination of your academic accommodations. The Office of Disability Services is located in Peltier Hall, Room 100-A. The phone number is (985) 448-4430 (TDD 449-7002).

ACADEMIC GRIEVANCES. The proper procedure for filing grade appeals or grievances related to academic matters is listed in Section 5 of the Code of Student Conduct and at he following link: http://www.nicholls.edu/documents/student_life/code_of_conduct.pdf .

CONTINUED LEARNING FOLLOWING AN EXTREME EMERGENCY: In order to make continued learning possible following an extreme emergency, students are responsible for: . reading regular emergency notifications on the NSU website; . knowing their Blackboard (or designated system) student login and password; . knowing how to use and access Blackboard (or university designated electronic delivery system); . being familiar with emergency guidelines; . evacuating textbooks and other course materials; . contacting faculty regarding their intentions for completing the course.

Faculty are responsible for: . their development in the use of the Blackboard (or designated) software; . having a plan for continuing their courses using only Blackboard and email; . continuing their course in whatever way suits the completion of the course best, and being creative in the continuation of these courses; . making adjustments or compensations to a student's progress in special programs with labs, clinical sequences or the like only in the immediate semester following the emergency.

CLASS DISRUPTIONS: The use of cellular phones, pagers or any other electronic personal devices is prohibited in class. Any infractions will result in dismissal from class and zero for the experiment. NOTEBOOK Notebooks must be written legibly to avoid loss of points. Prelab Due before beginning the experiment.  TITLE  DATE  PURPOSE Describe what is expected of the laboratory. This should be only one or two sentences, in your own words--do not copy from the manuals.  PROCEDURE A flow diagram is best. Abbreviated version of what you will be doing. Read the lab and be familiar with what will be happening. Summarize the steps.  DATA TABLE Listing of all of the reagents and solvents used in the experiment. List in table form only. mass used reagent or molecular moles used melting boiling solubility in or density product weight or produced point point solvents used. produced  CHEMICAL EQUATIONS Write all of the major chemical reactions and side reactions for the experiment. Include the amounts called for in the experiment (which is the limiting reagent?) and the theoretical yield. Not necessary for the distillation, melting point, or crystallization experiments.

You may not begin the experiment until the prelab section is completed and checked by instructor. Postlab  OBSERVATIONS All data and everything that occurs in lab as it happens. Colors, smells, amounts used, mixing, temperatures, apparatus used, time for reaction, spills if they occur etc. Draw pictures if appropriate, use tables, graphs, equations, etc. Record details such as Instrument name and maker, model number and serial number, chemical manufacturer, grade, lot number, expiration date, etc. This section cannot be too long. Spectra are also to be included with this section. Due at the end of lab.  CALCULATIONS This section will not be graded but must be included to show your work. Must be legible and organized.  CONCLUSION Report final results (positive or negative) and what evidence was used to make this decision (i.e., Based on FTIR spectra, the final product was . . . )  RESULTS/DISCUSSION This is the most important section—the analysis and interpretation of the results. This section, to be written concisely and legibly, includes all relevant results and supporting chemical theories and concepts pertaining to the experiment. Mechanisms and chemical equations for the product(s) should be included. Discussion of new techniques is expected. Percent yields and percent purity should be calculated and discussed. Any deviation of results from expected results (or class average) must be addressed and explained. You must be able to convey your understanding of what went on in the experiment. Include comparison, supporting evidence from relevant literature sources for the techniques and reactions. Discuss all spectral data provide noting specific values for peaks present and absent between starting material and final product. All figures, tables, graphs, and diagrams must be labeled.  REFERENCES : Proper citation of all material used in writing the report or to gather background material.  PRODUCTS Products submitted must be weighed to the nearest milligram, labeled, and turned in at the end of the laboratory. The label must include the following information: Name of Student Compound Name and Structure Mass of Product in Vial and Percent Yield Percent Purity (if available) Melting Point (if solid)