Saturday, May 20, 2017

organic chemistry - Carbonyl oxygen as nucleophile


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.




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periodic trends - Comparing radii in lithium, beryllium, magnesium, aluminium and sodium ions

Apparently the of last four, $\ce{Mg^2+}$ is closest in radius to $\ce{Li+}$. Is this true, and if so, why would a whole larger shell ($\ce{...