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

Organic Chemistry: A Guided Inquiry
2nd Edition
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Andrei Straumanis
Chapter19: Eas: Electrophilic Aromatic Substitution
Section: Chapter Questions
Problem 21E
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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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