1. Bicyclic keto compounds such as camphor react predictably with nucleophiles according to steric influences; this effect has been termed steric approach control. In contrast, the reaction of nucleophiles with simple acyclic and monocyclic keto compounds are influenced primarily by thermodynamic factors; this effect has been termed product development control. Given the following reaction, predict the identity of the major product and provide a rationale for your selection. OH NaBH4 t-Bu. t-Bu. t-Bu HO. ELOH 1 2

1. Bicyclic keto compounds such as camphor react predictably with nucleophiles according to steric influences; this effect has been termed steric approach control. In contrast, the reaction of nucleophiles with simple acyclic and monocyclic keto compounds are influenced primarily by thermodynamic factors; this effect has been termed product development control. Given the following reaction, predict the identity of the major product and provide a rationale for your selection. OH NaBH4 t-Bu. t-Bu. t-Bu HO. ELOH 1 2

Organic Chemistry

9th Edition

ISBN:9781305080485

Author:John E. McMurry

Publisher:John E. McMurry

Chapter19: Aldehydes And Ketones: Nucleophilic Addition Reactions

Section19.SE: Something Extra

Problem 28VC

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