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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![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.](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2F54b0d3a3-ae11-4f84-aab9-b22d2e40ad3e%2Fcd8a48da-3627-4448-a770-3c97f055b912%2Fsfgytnc.jpeg&w=3840&q=75)
Transcribed Image Text: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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