The structure of bromide formed from the treatment of exo − Norborneol with concentrated HBr should be written and its mechanism should be proposed with the curved arrows. The reason behind the formation of single diastereomer should be written. Concept introduction: Hydration of norbornene proceeds via norbornyl cation intermediate. This cation can be attacked from two positions. If the water attacks from above so that hydroxyl group ends up in above side it leads to exo − Norborneol while if the water attacks from beneath so that hydroxyl group ends up in below side it leads to endo − Norborneol illustrated as follows:

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Chapter 10.7, Problem 8E

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Interpretation:The structure of bromide formed from the treatment of exo−Norborneol with concentrated HBr should be written and its mechanism should be proposed with the curved arrows. The reason behind the formation of single diastereomer should be written.

Concept introduction:Hydration of norbornene proceeds via norbornyl cation intermediate. This cation can be attacked from two positions. If the water attacks from above so that hydroxyl group ends up in above side it leads to exo−Norborneol while if the water attacks from beneath so that hydroxyl group ends up in below side it leads to endo−Norborneol illustrated as follows:

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