Aldehydes and ketones have electrophilic centres at their carbonyl C, since the carbonyl O polarises the bond and attracts electron density towards itself on account of its high electronegativity. But despite this electron density, the oxygen atom hardly ever acts as a nucleophilic centre. If it all, it is the alpha C, which in enols and enolates acts as a nucleophile. I only know of the Wittig reaction in which the O also reacts with the reagent (the P atom in this case). Is there any reason for the low reactivity of the oxygen? It is joined to C with a pi bond, which in any case is easy to break on attack by a reagent.

Aldehydes and ketones have electrophilic centres at their carbonyl C, since the carbonyl O polarises the bond and attracts electron density towards itself on account of its high electronegativity. But despite this electron density, the oxygen atom hardly ever acts as a nucleophilic centre. If at all, it is the alpha C, which in enols and enolates acts as a nucleophile. I only know of the Wittig reaction in which the O also reacts with the reagent (the P atom in this case). Is there any reason for the low reactivity of the oxygen? It is joined to C with a pi bond, which in any case is easy to break on attack by a reagent.