Microscale glassware and analytical techniques are used to study fundamental organic reactions and the synthesis of organic compounds. Techniques include distillation (simple, fractional, and steam), crystallization, and extraction. Analysis of compounds includes melting points, boiling points, refractive indices, infrared spectroscopy, and chromatography (gas, thin layer, column). This meets the Organic Laboratory requirement necessary to enter into Pharmacy, Medical, Dental, and Veterinary schools. Many schools require students to also take Organic Lab II CHEM-244. Approximately one hour of lecture and three hours of lab per week.
Goals, Topics, and Objectives
After completing Chemistry 243, students should:
- Be skilled in the use of specialized instrumentation.
- Be adept at making careful measurements and observations.
- Be able to purify organic compounds.
- Be able to keep an up-to-date laboratory notebook.
- Be experienced in using critical thinking and the scientific method.
- Be more familiar with the work of professional chemists.
- Be able to use the chemical literature for research.
- Be able to write detailed, accurate, and thorough scientific reports.
- Be prepared to enroll in higher level classes in chemistry.
- Lab Procedures and Safety
- Using the Chemical Literature (primary and secondary references)
- Proper Laboratory notebook preparation and maintenance
- Measurement of Physical Properties: boiling point, melting point, and refractive index.
- Distillation: Simple Distillation (semimicro); Fractional Semimicroscale Distillation (FSMD)
- Solvent Extraction and Determining a Partition Coefficient; Solvent Extraction using Acid-Base Properties
- Williamson Ether Synthesis
- Esterification: Isoamyl Acetate Synthesis
- Infrared Spectroscopy (students will learn how to independantly operate a modern spectrophotometer)
- Photochemical Isomerization of Alkenes: Isomerization of cis-1,2-Dibenzoylethylene
- Thin Layer Chromatography (TLC)
- Infrared unknowns
- The Wittig reaction and the Horner-Wadsworth-Emmons-Arbuzov variation
- Diels-Alder Reaction: Synthesis of 9,10-Dihydroanthracene-9,10-a,b-Succinic acid anhydride
- Diazonium Coupling Reaction: Synthesis of Methyl Red
- Friedel-Crafts Acylation of Ferrocene
- Cost analysis
Scaleup a reaction from microscale to multi-tonne scale and perform a cost analysis.
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.*
- Operate proficiently 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, hazardous chemicals.
- Employ proficiently the following techniques: microscale distillation; recrystalization; infrared sampling; melting point determination; boiling point determination; solvent evaporation; solvent extraction; 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.
- Demonstrate the ability to 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 judge the reliability of various resources.
- Perform a cost analysis using chemical catalogs for a large scale organic synthesis.*
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:
- Performance in the lab setting.
- Laboratory reports.
- Lab material and skills will be assessed on a lab practical midterm and final. These exams have both practical and theoretical portions. Both of these exams last 4 hours.
- In Class Questions
- Pre Class Questions, both written and electronic.
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)