Evaluating Possible Reactions

## Reactant

## Reagents

CH3MgBr in ether H2O workup | PCC in CH2Cl2 (pyridinium chlorochromate) | 10% KOH heat to reflux | (i) LiAlH4 in ether (ii) H2O
NaBH4 (in ethanol) | (i) DIBAH, 1eq. -78° C (diisobutylaluminum hydride); (ii) H2O | (i) C6H5Li, 1eq. -28° C (ii) H2O, heat | HNO3 & H2SO4 heat
Br2 FeBr3 & heat | NaCN (in acetone) | (i) Mg filings in ether (ii) acetone, followed by water. | (i) Hg(OAc)2 in water (ii) NaBH4
NBS light or heat (N-bromosuccinimide) | (C6H5)3P=CH2 (in ether) | 10% H2SO4 heat to reflux | KMnO4 (aqueous) heat to reflux

Mark those reagents you believe will react with the selected compound (shown in the colored box).

This script written by William Reusch, Dept. of Chemistry, Michigan State University. Please send comments and corrections to whreusch@pilot.msu.edu.