Microscale glassware and analytical techniques are used in this follow-up course to CHEM-243. The primary focus of this course is multi-step organic syntheses and proper research techniques. Practical techniques from the previous course will be applied towards the synthesis of a novel polyaromatic hexaphenylbenzene, an antibacterial drug sufanilamide, triphenylmethanol, and cholesta-3,5-dien-3-ol acetate. Products will be analyzed (melting point/boiling point, infrared analysis, chromatographic properties (TLC, GC), solubility, refractive index) and compared to literature values to verify their veracity. Research will involve a critical analysis of competitive synthetic methods of a recent pharmaceutical agent. The sequence CHEM-241, CHEM-242 (Lecture I and II) and CHEM-243, CHEM-244 (Laboratory I and II) will transfer to all Michigan universities to meet their Organic Chemistry requirements for Science Majors. Approximately one hour of lecture and three hours of lab per week.
Goals, Topics, and Objectives
After completing Chemistry 244, students should be:
- Skilled in the use of specialized instrumentation.
- Adept at making careful measurements and observations.
- Able to purify organic compounds.
- Able to keep an up-to-date laboratory notebook.
- Experienced in using critical thinking and the scientific method.
- More familiar with the work of professional chemists.
- Able to use the chemical literature for research.
- Prepared to enroll in higher level classes in chemistry and biochemistry.
- Lab Safety
- Using the Chemical Literature (primary and secondary references)
- Proper Laboratory notebook preparation and maintenance
- Further exploration of Research Methods
- Grignard Reaction With A Ketone: Triphenylmethanol
- Hydroboration-Oxidation of an Alkene: Octanol
- Multistep Organic Synthesis I:
- The Benzoin Condensation of Benzaldehyde: Benzoin
- Copper(II) Ion Oxidation of Benzoin: Benzil
- Tetraphenylcyclopentanedienone
- Acetylation of Aniline: 2,2,2-Trifluoroacetanilide
- Synthesis of (E)-Stilbene using a Horner-Wadsworth-Emmons-Arbuzov protocol
- Bromination of (E)-Stilbene: meso-Stilbene Dibromide
- Dehydrohalogenation of meso-Stilbene Dibromide: Diphenylacetylene Hexaphenyl Benzene
- Multistep Organic Synthesis II:
- Chlorosulfonation of 2,2,2-Trifluoroacetanilide: p-(Trifluoroacetamido)benzenesulfonyl chloride
- Preparation of Arene Sulfonamide: Sulfanilamide
Students who successfully complete the assignments of this course should be able to:
- Demonstrate various levels of proficiency with laboratory skills used by scientists. Each lab objective will be listed in the laboratory assignments. Each objective will be characterized as requiring familiarity, competence, or expertise on the part of the student. During the laboratory periods, the student will then be assessed to determine whether they have the level of proficiency expected.
- Demonstrate the use of critical thinking skills in the analysis of experimental data.
- Demonstrate proficiency with the use of the following equipment: microscale, semi-microscale and traditional glassware, melting point apparatus, refractometers, infrared spectrophotometer, thin layer chromatographic plates, fume hoods, safety glasses, burners, hot plates, syringes, rotary evaporator, and hazardous chemicals.
- Demonstrate proficiency with the following techniques: microscale distillation, recrystalization, infrared sampling, melting point determination, boiling point determination, solvent evaporation, delivery of microscale quantities, and hazardous waste disposal.
- Recognize and give examples of the importance of searching for patterns when one is studying the sciences and carrying out investigations and/or experiments.
- Describe and analyze reaction mechanisms and their relationship to experimental manipulation.
- Predict the physical properties of molecules based on an understanding of functional groups.
- Show familiarity with traditional library resources and electronic media and use criteria with which to discriminate the reliability of various resources.
- Determine the identity of an unknown using formula analysis, NMR data, infrared data, density and refractive index.
Assessment and Requirements
Student assessment is built into the course objectives. Objectives were written using wording which allows their achievement to be measured. Students will be assessed on:
- Laboratory reports.
- Lab course material and skills will be assessed on a lab final. This exam will have both practical and theoretical portions. This exam last 4 hours.
- In Class Questions
- Pre Class Questions, both written and electronic.
- A research project.
Text book is designed for use by students entering into health related careers such as Pharmacy, Medical, Dental, and Veterinary. One such book being; Microscale Organic Laboratory, 4th Ed. Dana W. Mayo, Ronald M. Pike, Peter K. Trumper NewYork: John Wiley & Sons, Inc., 2000.
Outcomes
- Natural Sciences
- Scientific Reasoning
- Category 6: Natural Sciences (Lecture Only)