TEMPO Oxidation Post-Lab Questions Name: Consider the following three oxidation reactions. OH CrO3. H2SO H20 OH OH PCC CH2Cl2 OH TEMPO H20/ CH2Cl2 HWI. acid (1)? Specify what it is about a Jones oxidation (I) that drives the oxidation to the carboxylic HW2. In contrast, specify what is it about a PCC oxidation that only oxidizes the alcohol to the aldehyde and stops (I1) ?: HW3. Read the following excerpt from a TEMPO review article (Tojo, G. Fernandez, M.I. Oxidation of Alcohols to Carboxylic Acids A Guide to Current Common Practice, 2007 pg 82) "In 1987, Anelli et al. made a key contribution to TEMPO-mediated oxidations by showing that the very cheap reagent chlorine bleach (aqueous NaOCI) can function very effectively as a stoichiometric oxidant for alcohols in the presence of traces of 4-MeO-TEMPO. a reaction run at 0_C in a biphasic CH2C12-water mixture in the presence of excess of NaOCI, NaHCO3, KBr, and catalytic 4-MeO-TEMPO for oxidation to aldehydes. Under these conditions the oxidation to acids is quite slow. If the acid is desired, it is advisable to add a phase-transfer catalyst to speed up the oxidation." They established a protocol involving 209