Mechanism of conversion of allyl alcohol into propenal by using pcc
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Pyridinium chlorochromate (PCC) is a very useful reagent for the oxidation of organoboranes to carbonyl compounds in mildly alkaline and anhydrous conditions.89 As well as oxidizing (secondary alkyl)boranes to ketones,90,91 PCC oxidizes (primary alkyl)boranes to aldehydes in excellent yields (equation 47).89 The latter transformation cannot be accomplished with chromic acid. The reagent tolerates the presence of alkene, ester and acetal groups.90
(47)
The observation92 that trialkylboranes are oxidized to aldehydes as fast as the free alcohols and much faster than acetates prompted the introduction of an efficient one-pot procedure for the conversion of acids to aldehydes (equation 48) in 69–82% isolated overall yields.93
PCC oxidizes gem-diboryl compounds to ketones.84