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Chemistry / Organic Chemistry 8 / Chapter 17 / Problem 66SP

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

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A graduate student tried to make o-fluorophenylmagnesium

Chapter 11, Problem 66SP

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QUESTION:

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.

\(B r\)

Equation transcription:

$Br$

Text transcription:

B r

Questions & Answers

QUESTION:

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.

\(B r\)

Equation transcription:

$Br$

Text transcription:

B r

ANSWER:

Solution 66SP

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