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Students are tasked with planning and executing the synthesis of a novel fluorous dye molecule and using it to explore a fluorous affinity chromatography separation technique, which is the first implementation of this technique in a teaching laboratory.
Key elements of the project include gradually introducing students to the use of the chemical literature to facilitate their searching, as well as deliberate constraints designed to force them to think critically about reaction design and optimization in organic chemistry.
The project also introduces students to some advanced laboratory practices such as Schlenk techniques, degassing of reaction mixtures, affinity chromatography, and microwave-assisted chemistry. This provides students a teaching laboratory experience that closely mirrors authentic synthetic organic chemistry practice in laboratories throughout the world.
To date, many elegant examples of engaging, individual-inquiry laboratories have been reported. The course is separate from the pre- or co-requisite organic lecture course and meets twice weekly for 3-h sessions, in sections each led by a graduate teaching assistant TA.
In so doing, a secondary goal of exposure to modern synthetic techniques, including microwave-accelerated synthesis and affinity chromatography, could be achieved. In particular, chromatography is an important part of the everyday life of synthetic organic chemists, but relatively little chromatography is carried out in organic teaching labs.
Reasons for this omission may include the safety issues of packing and running columns with standard silica gel inhalation hazard in pressurized glassware explosion hazard , as well as the cost of the silica gel and solvent disposal for single-use columns.
The use of fluorous affinity chromatography with prepacked columns could make a chromatography process more feasible in teaching labs: the preparation issues are avoided, and the columns can be reused multiple times.
Moreover, an understanding of affinity chromatography and noncovalent interactions is particularly relevant for students who go on to pursue work in biochemistry and areas of biology where it is a common technique.
Fluorous chemistry 8 , 9 is a rapidly growing subfield of organic chemistry that has also gained attention in the context of green chemistry. Our interactive player makes it easy to find solutions to Modern Projects and Experiments in Organic Chemistry problems you're working on - just go to the chapter for your book.
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