The tosylate of a primary alcohol normally undergoes an S2 reaction with hydroxide ion to give a primary alcohol. Reaction of this tosylate, however, gives a compound of molecular formula C,H,0. OH NaOH C,H190 OTs Propose a structural formula for this compound and a mechanism for its formation.

The tosylate of a primary alcohol normally undergoes an S2 reaction with hydroxide ion to give a primary alcohol. Reaction of this tosylate, however, gives a compound of molecular formula C,H,0. OH NaOH C,H190 OTs Propose a structural formula for this compound and a mechanism for its formation.

Organic Chemistry

8th Edition

ISBN:9781305580350

Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Chapter10: Alcohols

Section: Chapter Questions

Problem 10.43P: The tosylate of a primary alcohol normally undergoes an SN2 reaction with hydroxide ion to give a...

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Question

The tosylate of a primary alcohol normally undergoes an S2 reaction with hydroxide
ion to give a primary alcohol. Reaction of this tosylate, however, gives a compound of
molecular formula C,H,0.
OH
NaOH
C,H190
OTs
Propose a structural formula for this compound and a mechanism for its formation.

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