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A graduate student tried to make o-fluorophenylmagnesium

Organic Chemistry | 8th Edition | ISBN: 9780321768414 | Authors: L.G. Wade Jr ISBN: 9780321768414 33

Solution for problem 66SP Chapter 17

Organic Chemistry | 8th Edition

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Organic Chemistry | 8th Edition | ISBN: 9780321768414 | Authors: L.G. Wade Jr

Organic Chemistry | 8th Edition

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Problem 66SP

A graduate student tried to make o-fluorophenylmagnesium bromide by adding magnesium to an ether solution of o-fluorobromobenzene. After obtaining puzzling results with this reaction, she repeated the reaction by using as solvent some tetrahydrofuran that contained a small amount of furan. From this reaction, she isolated a fair yield of the compound that follows. Propose a mechanism for its formation.

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Textbook: Organic Chemistry
Edition: 8
Author: L.G. Wade Jr
ISBN: 9780321768414

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A graduate student tried to make o-fluorophenylmagnesium