Oxidation Procedure: Suspend the PCC oxidant mixture (1.70 g, 2.64 mmol) in meth

Question

Oxidation Procedure: Suspend the PCC oxidant mixture (1.70 g, 2.64 mmol) in methylene chloride (10 mL) with magnetic stirring in a 50-mL Erlenmeyer flask and add 4-nitrobenzyl alcohol (200 mg, 1.31 mmol). Stir the mixture for 30 min at room temperature. Monitor the reaction by TLC (30% ethyl acetate in petroleum ether, visualize with UV). Add Florisil (2 g) to the reaction mixture and stir vigorously for 5 min. Filter the reaction mixture using an additional 10 mL of ether. Concentrate in sand bath to remove volatile solvent. Load compound on silica gel column and elute with 15% methylene chloride in petroleum ether. Note: Some questions will focus on the procedure, as written. Others will ask about modifying this procedure for use of a different alcohol. If lab run out of 4-nitrobenzyl alcohol. If you wanted to adapt this experiment to oxidize benzyl alcohol instead, keeping all other reagent amount the same, how much benzyl alcohol reagen (in micro litter) would need to use?what is the role of methylene chloride in this reaction? Acid catalyst, base, oxidizing agen, solvent or drying agent.

Explanation / Answer

For benzyl alcohol we want use same equivalent like nitrobenzene alcohol since here alcohol is oxidized to aldehyde.

b.

Here methylene chloride is solvent, just a medium for reaction.

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