RAMAPO COLLEGE OF NEW JERSEY ORGANIC CHEMISTRY II LABORATORY SPRING 2009 INSTRUCTOR: Dr. Robert J. Shine Office: G-250 Phone: Office 201-684-7719 Home 201-444-4150 Office Hours: T 1:00-2:00 or by appointment E-Mail Address: bshine@ramapo.edu COURSE DESCRIPTION: This is a continuation of Organic Chemistry I laboratory. The techniques learned last semester will be used in the synthesis of organic compounds. As such, laboratory work will illustrate modern techniques of purification, identification and synthesis. Qualitative organic analysis will be covered in the later half of this semester. This course is required for Chemistry and Biology majors. Prerequisite: Organic Chemistry I (Chem 210 & 211). COURSE TEXT: The text for these experiments in on my web page or on Luminis. The web address is http://phobos.ramapo.edu/~bshine/org2lab/content.htm OPTIONAL TEXT: MACROSCALE AND MICROSCALE ORGANIC EXPERIMENTS by Kenneth Williamsom, Houghton Mifflin Company Fourth Edition, 2003 (ISBN 0-618-19702-8) Third Edition is also suitable SCHEDULE OF EXPERIMENTS: NOTE THAT THE LAB WEEK BEGINS ON TUESDAY FOR THIS SEMESTER Week 1: T 1/20 Check in, safety and lab procedures Week 2: T 1/27 Sodium borohydride reduction Synthesis of hydrobenzoin Week 3: T 2/3 Hypochlorite oxidation - green chemistry Synthesis of benzoic acid Week 4: T 2/10 Grignard reaction Synthesis of triphenylmethanol Week 5: T 2/17 Diels Alder reaction Reaction of a-phellandrene with maleic anhydride Week 6: T 2/24 Electrophilic aromatic substitution Nitration of methyl benzoate Week 7: T 3/3 Friedel-Crafts alkylation Synthesis of 1,4-di-t-butyl-2,5-dimethoxybenzene Week 8: T 3/10 Qualitative organic analysis Analysis of aldehydes and ketones Introduction to Sim-Org computer program Week 9: T 3/17 Spring break - no class (Monday 3/16 to Sunday 3/22) Week 10: T 3/24 Aldol condensation reactions Synthesis of dibenzalacetone and Synthesis of trans-4-methylchalcone from acetophenone and 4-methylbenzaldehyde Week 11: T 3/31 Williamson synthesis Synthesis of phenacetin Week 12: T 4/7 Analysis of carbohydrates Week 13: T 4/14 Microwave hydrolysis of methyl benzoate - green metrics Synthesis of benzoic acid Week 14: T 4/21 Review - green metrics, Sim-Org and checkout Week 15: T 4/28 Final Examination TESTING AND GRADING: Please see the Course Procedures page for important details about this course. In general, you will do the experimental work in pairs. However, each student must turn in a lab report for the work done. Lab reports are due at the very beginning of the next regularly scheduled lab period. The lab report should be complete at the time you submit it. If more data needs to be collected for an experiment that was not finished in the prior lab period, the Instructor will hand out a sheet where new data may be recorded. The Instructor will give exact details of the procedure to follow in such cases. A lab report that is submitted late will receive a grade penalty. No lab report will be accepted after other students receive their graded lab reports for a given experiment. Generally, this means that no lab report will be accepted after two weeks from the time the experiment was first started. You may have a short quiz at the beginning of each lab period to ensure that you have studied the experiment that will be done that day. Your grade for this laboratory course will be computed according to the format given on the Course Procedures page. If you are registered with the Office of Specialized Services, please see me as soon as possible so that we may discuss the accommodations that will be needed. Please see me at any time if you wish to discuss your grade in the course. You must keep all graded lab reports and tests until you receive your final grade in case there are questions about your grade. Make-up labs will not be given.