Laboratory experiment demonstrates a multi-step synthesis in organic chemistry, highlighting green chemistry techniques.
This laboratory experiment combines simple one-step reactions into a capstone experience for the undergraduate organic chemistry laboratory. An environmentally benign haloform oxidation of acetophenone to benzoic acid begins this multi-step sequence. Yields of a Fischer esterification of benzoic acid to methyl benzoate are optimized with a modified Dean-Stark trap. Lastly, the methyl benzoate is converted through a classical Grignard reaction into triphenylmethanol. This sequence utilizes many of the techniques and skills learned throughout the organic chemistry laboratory curriculum and offers improvements in yields of the reactions. Additionally, the experiment allows for discussion of “green” chemistry techniques and reinforces several concepts presented in the lecture portion of the course.
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Blunt et al. (2004) studied this question.
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