The following sequence of methylation and Hofmann elimination was used in deter- mining the structure of this bicyclic amine. Compound B is a mixture of two isomers. CH3 1. CH3I 2. Ag,O, H,O 4. CH3I 5. Ag,O, H,О C10H19N C3H12 3. heat 6. heat (C,H17N) (A) (В)
The following sequence of methylation and Hofmann elimination was used in deter- mining the structure of this bicyclic amine. Compound B is a mixture of two isomers. CH3 1. CH3I 2. Ag,O, H,O 4. CH3I 5. Ag,O, H,О C10H19N C3H12 3. heat 6. heat (C,H17N) (A) (В)
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
Chapter5: Alkenes: Bonding, Nomenclature, And Properties
Section: Chapter Questions
Problem 5.31P
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Question
Suppose you were given the structural formula of compound B but only the
molecular formulas for compound A and the starting bicyclic
information, is it possible, working backward, to arrive at an unambiguous structural formula for compound A? for the bicyclic amine?
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