Abstract
This project focuses on the design of an upper level synthetic organic chemistry course, which is intended as a bridge between undergraduate organic chemistry courses and graduate school. It will allow students to gain useful experience in the laboratory before entering graduate or professional school. The course will allow students to advance their abilities to evaluate novel work. Students will judge classmates’ proposed synthetic routes, utilizing a peer-review approach. Novel synthetic routes focused on carbonyl chemistry will be designed, and the target compounds obtained will be purified and characterized throughout the course of the class. Research thus far has focused on developing both a starting compound and target molecule library. Proposed starting materials include Ethyl acetoacetate, Ethyl crotonate, 3-(2-Hydroxyphenyl) propionic acid, and acetic anhydride. The following target molecules were identified thus far: ethyl-2,4-dioxo-3-chromane carboxylate and ethyl-4,6-dihydroxy-2- methylcyclohex-2-ene-1-carboxylate. Different reaction types that will be utilized are the haloform reaction, keto-enol tautermerization, oxidation, and intramolecular ring formation. Successful syntheses will culminate with compound purification, utilizing column chromatography and HPLC methods. Full characterization will also be carried out on these products, employing FT-IR, GC-MS and NMR methods. At every course offering, new starting and target compounds will identified for students to design synthetic routes for. Considerations taken for this project are the timeliness of the reactions, as well as the safety and affordability of the compounds. It is designed to be affordable for a wide variety of school budgets.
Faculty Sponsors
Dr. Beatrix Aukszi
Project Type
Event
Location
Alvin Sherman Library
Start Date
4-4-2014 1:00 PM
End Date
4-4-2014 5:30 PM
Complete Synthesis of Carbonyl-Containing Compounds: A Guided Inquiry Approach
Alvin Sherman Library
This project focuses on the design of an upper level synthetic organic chemistry course, which is intended as a bridge between undergraduate organic chemistry courses and graduate school. It will allow students to gain useful experience in the laboratory before entering graduate or professional school. The course will allow students to advance their abilities to evaluate novel work. Students will judge classmates’ proposed synthetic routes, utilizing a peer-review approach. Novel synthetic routes focused on carbonyl chemistry will be designed, and the target compounds obtained will be purified and characterized throughout the course of the class. Research thus far has focused on developing both a starting compound and target molecule library. Proposed starting materials include Ethyl acetoacetate, Ethyl crotonate, 3-(2-Hydroxyphenyl) propionic acid, and acetic anhydride. The following target molecules were identified thus far: ethyl-2,4-dioxo-3-chromane carboxylate and ethyl-4,6-dihydroxy-2- methylcyclohex-2-ene-1-carboxylate. Different reaction types that will be utilized are the haloform reaction, keto-enol tautermerization, oxidation, and intramolecular ring formation. Successful syntheses will culminate with compound purification, utilizing column chromatography and HPLC methods. Full characterization will also be carried out on these products, employing FT-IR, GC-MS and NMR methods. At every course offering, new starting and target compounds will identified for students to design synthetic routes for. Considerations taken for this project are the timeliness of the reactions, as well as the safety and affordability of the compounds. It is designed to be affordable for a wide variety of school budgets.
