Question

Give the product expected when the following alcohol reacts with pyridinium chlorochromate (PCC). (Assume that PCC is present in excess.)

Answer 1

The mechanism of the action of pcc is as follows

How it works Oxidation of primary alcohols to aldehydes The alcohol coordinates to the chromium(VI) atom, displacing chlorine, which then acts as a base, resulting in oxidation of the alcohol and reduction of Cr(VI) to Cr(IV) Cl pcc-3 copy OH proton transfer :Ci: HHO но, "Он Cr(lV) Pyridinium chloride

as we can see the the caron having OH should atleast have 1 H to be abstracted be the Cl- , but in the carbon 2 ..there is no H on this. thus it will not go under oxidation.

only C1 will go under oxidation as shown

OH PCC OH OH