In a hypochlorite oxidation reaction, cyclohexanol plus NaOCL & aq HOAc results in cyclohexanone. The intermediate in this reaction in ROCl where R = cyclohexyl.

Question

a.) Show how this intermediate decomposes to product in a E2-like reaction even at pH = 4-5; consider what the likely base is.

b) Hypochlorous esters of primary & secondary alcohols are hard to store, whereas t-BuOCL is commercially available. Why doesn't it undergo the reaction in part a.)?

Answer 1

Nevermind! Figured it out :)

Answer 2

Please! What is the answer? Enlighten me!