Elimination of HBr from 2-bromonorbornane gives only

Chapter 9, Problem 9.41

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Elimination of HBr from 2-bromonorbornane gives only 2-norbornene and no 1- norbornene. How do you account for the regioselectivity of this dehydrohalogenation? In answering this question, you will fi nd it helpful to look at molecular models of both 1-norbornene and 2-norbornene and to analyze the strain in each. 2-Bromonorbornane 2-Norbornene H Br H H H 1-Norbornene H H H H H H

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