Organic Chemistry I Laboratory

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چکیده

For many years the dehydration of 2-methylcyclohexanol to a mixture of alkenes has been carried out in college organic chemistry labs to demonstrate the application of Zaitzev’s rule and the occurrence of the E1 reaction mechanism in alcohol dehydration reactions. In 1994 David Todd, then a chemistry professor at Pomona College, was distilling the product alkenes out of the reaction mixture when he was interrupted by an urgent summons to lunch with the chemistry department secretary, Evelyn Jacoby. Upon returning from lunch he decided, out of curiosity, to replace the distillation receiver with a new one and collect a second fraction. He then worked up both fractions and analyzed them both by gas chromatography. Much to his surprise, the second fraction contained a markedly lower percentage of the expected product, 1-methylcyclohexene, than the first. Because his decision to replace the receiver with a new one was the direct result of the secretary’s request, Professor Todd named this unexpected result the “Evelyn effect.”

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تاریخ انتشار 2000