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

(4) Provide the reagents necessary to carry out the following synthesis. + enantiomer (A) (1) (i) BH3, (ii) H₂O2, NaOH; (2) NaOEt JATOT (B) (1) (i) BH3, (ii) H₂O2, NaOH; (2) TsCl, pyridine; (3) KOC(CH3)3 (C) (1) H3O+, (2) TsCl, pyridine, (3) KOC(CH3)3 (D) (1) HBr (no peroxides); (2) NaOEt

Why does cyclohexanol have a pK, of 18 and phenol, despite its similarities in structure, have a pK, of 10? Phenol has a resonance-stabilized conjugate base, which increases the stability of the base and favors its formation Cycohexanol has a resonance-stabilized structure, which increases its stability and reduces the likelihood that it will react to form a conjugate base Phenol has a resonance-stabilized conjugate base, which decreases the stability of the base and inhibits its formation Cycohexanol has a resonance-stabilized conjugate base, which increases the stability of the base and favors its formation Phenol has a resonance-stabilized conjugate base, which decreases the stability of the base and favors its formation