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

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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.
ОН
NABH4
t-Bu.
t-Bu
t-Bu.
ELOH
1
2
Transcribed Image Text: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. ОН NABH4 t-Bu. t-Bu t-Bu. ELOH 1 2
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