Discussion
Suggest most suitable reagent/condition for the following conversion :
Answer: B
The reagent is TEMPO (2.0%); NaOCl (1.25 eq), CH2Cl2.
The substrate has a primary and a secondary alcohol, and only the primary one must become an aldehyde. The Anelli oxidation, catalytic TEMPO with bleach as the stoichiometric oxidant, works through an oxoammonium ion that is bulky and reacts much faster with unhindered primary alcohols. It stops at the aldehyde without over-oxidation, and with a limited amount of NaOCl the secondary alcohol is left alone.
MnO2 oxidises only allylic and benzylic alcohols, and neither alcohol here is activated. PDC oxidises primary and secondary alcohols alike, so it would also give the ketone. DMDO is mainly an epoxidising agent, and when it does oxidise alcohols it attacks secondary ones in preference to primary.
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