2-(1-hydroxyprop-2-yl) cyclopentanol reacts with pyridinium chlorochromate in dioxane under reflux. What product is formed?(Hint: assume that you have sufficient quantities of oxidizer to perform all possible reactions.)

Question

2-(1-hydroxyprop-2-yl) cyclopentanol reacts with pyridinium chlorochromate in dioxane under reflux. What product is formed?(Hint: assume that you have sufficient quantities of oxidizer to perform all possible reactions.)
2-(1-hydroxyprop-2-yl) cyclopentanol reacts with pyridinium chlorochromate in dioxane under reflux. What product is formed?(Hint: assume that you have sufficient quantities of oxidizer to perform all possible reactions.) A) I B) II C) III D) IV

Quizplus · Accepted Answer

The given compound can undergo oxidation on the hydroxyl group and/or the isopropyl group. Pyridinium chlorochromate (PCC) is a mild oxidizing agent that selectively oxidizes primary alcohols to aldehydes and secondary alcohols to ketones. In this case, the hydroxyl group is a primary alcohol so it will be oxidized to an aldehyde. The isopropyl group does not undergo oxidation with PCC.
 
Therefore, the product formed will be III, 2-(1-formylprop-2-yl) cyclopentanol.

2-(1-Hydroxyprop-2-Yl) Cyclopentanol Reacts with Pyridinium Chlorochromate in Dioxane Under Reflux