Alcohol Oxidation Reactions (PCC, Jones Reagent)

Problem # 679

Compound A (C5H12O) is oxidized using aqueous chromium (Jones reagent) to compound B (C5H10O2), which is then treated with methanol under acidic conditions to yield compound C (C6H12O2) and water.

The 1H NMR of compound C is shown below. Determine the structures of compounds A, B, and C.

Problem # 678

Draw the structure of the major organic product from each reaction sequence.