Reaction of the tertiary amine tropinone with (bromomethyl)benzene (benzyl bromide) gives not one but two quaternary ammonium

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Reaction of the tertiary amine tropinone with (bromomethyl)benzene (benzyl bromide) gives not one but two quaternary ammonium salts, A and B. 

H3C > A + B [Cı3HNO]* Br + -CH,Br Tropinone (C,H,NO)

Compounds A and B are stereoisomers that are interconverted by base; that is, base treatment of either pure isomer leads to an equilibrium mixture of the two. 

(a) Propose structures for A and B.

(b) What kind of stereoisomers are A and B? 

(c) Suggest a mechanism for the equilibration of A and B by base.

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Organic Chemistry structure and function

ISBN: 978-1429204941

6th edition

Authors: K. Peter C. Vollhardt, Neil E. Schore

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