Chapter 9, Problem 89AP

starting reactant IV target + enantiomer 1) BH3, THF 2) H₂O2, NaOH, H₂O 1) Hg(OAc)2, THF, H₂O (or ROH) 2) NaBH4 D2, Pt/C H₂, Pt/C D2, Lindlar catalyst or Ni₂B H₂, Lindlar catalyst or Ni₂B NaNH, OH/H₂O or SH/H₂S H₂O/H₂O 1) 03 2) H₂O 1) 03 2) (CH3)2S HBr, w/ROOR HBr, (cold, dark, no ROOR) Naº, NH3(e) NBS (trace Br2), light HgSO4, H2SO4, H₂O Naº, ROH 1) Sia₂BH, THF 2) H2O2, NaOH, H₂O H3O/ROH or H₂O*/RSH OR/ROH or SR/RSH 1) OsO4, NMO 2) NaHSO3, H₂O 1) MCPBA (peroxy acid) 2) H3O, H2O (or ROH or RSH) KMnO4 (warm, concentrated) Br₂/H₂O Br₂, heat or light Br2, cold, dark, no peroxides (CH3)3CO(CH3)3COH ROH or RSH H₂O KMnO4/OH (cold, dilute)

None

Indicate whether the ability of atoms to associate with each other depends on electron affinity.