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Fluoride ion is usually a poor leaving group because it is

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

Solution for problem 21P 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 21P

Fluoride ion is usually a poor leaving group because it is not very polarizable. Fluoride serves as the leaving group in the Sanger reagent (2,4-dinitrofluorobenzene), used in the determination of peptide structures (Chapter 24). Explain why fluoride works as a leaving group in this nucleophilic aromatic substitution, even though it is a poor leaving group in the SN1 and SN2 mechanisms.

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

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Fluoride ion is usually a poor leaving group because it is