Abstract
The focus of this investigation is to aid the development of a new advanced synthetic organic chemistry course, aiming for the development of possible synthetic routes of aromatic systems. Through a guided inquiry approach, students will be in charge of designing an entire synthetic route to develop a target compound. Proposed projects will be presented in-class, and feedback will be provided using a peerreview system to allow for improvements. Refined routes will then be carried out in the laboratory. Target compounds will then be purified, using common organic purification methods, such as column chromatography and HPLC, and then subjected to full characterization using methods, such as FT-IR, GC-MS, NMR, and UV/Vis spectroscopy.
This project has focused on the development of a library of naturally occurring target molecules, and suitable starting compounds. The difficulty and originality of this project resides from the fact that no synthetic routes for the target molecules have been published to date. Further difficulty originated from choosing starting and target compounds that were fiscally reasonable, challenging but not beyond an undergraduate student’s ability to synthesize, and above all else safe. Over the last several months synthetic targets that have been investigated are 5-(bromomethyl)-1,3-dihydroxy-9H-xanthen-9-one and 3-[N’-(3-bromo-2-hydroxy-5-nitrophenyl) hydrazinecarbonyl] propanoic acid. Additionally, some starting compounds that are currently being utilized are 3-methylsalicylic acid, 2-amino-4-nitrophenol, benzene-1,4-diamine, and sulfanilic acid. Proposed synthetic routes will be fully tested in the laboratory and obtained target molecules will be purified and characterized. The developed target molecule library will be the starting point for this guided inquiry course.
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
Guided Inquiry: Synthetic Investigation of Aromatic Systems
Alvin Sherman Library
The focus of this investigation is to aid the development of a new advanced synthetic organic chemistry course, aiming for the development of possible synthetic routes of aromatic systems. Through a guided inquiry approach, students will be in charge of designing an entire synthetic route to develop a target compound. Proposed projects will be presented in-class, and feedback will be provided using a peerreview system to allow for improvements. Refined routes will then be carried out in the laboratory. Target compounds will then be purified, using common organic purification methods, such as column chromatography and HPLC, and then subjected to full characterization using methods, such as FT-IR, GC-MS, NMR, and UV/Vis spectroscopy.
This project has focused on the development of a library of naturally occurring target molecules, and suitable starting compounds. The difficulty and originality of this project resides from the fact that no synthetic routes for the target molecules have been published to date. Further difficulty originated from choosing starting and target compounds that were fiscally reasonable, challenging but not beyond an undergraduate student’s ability to synthesize, and above all else safe. Over the last several months synthetic targets that have been investigated are 5-(bromomethyl)-1,3-dihydroxy-9H-xanthen-9-one and 3-[N’-(3-bromo-2-hydroxy-5-nitrophenyl) hydrazinecarbonyl] propanoic acid. Additionally, some starting compounds that are currently being utilized are 3-methylsalicylic acid, 2-amino-4-nitrophenol, benzene-1,4-diamine, and sulfanilic acid. Proposed synthetic routes will be fully tested in the laboratory and obtained target molecules will be purified and characterized. The developed target molecule library will be the starting point for this guided inquiry course.
