I've been trying to look for an answer for a while but I can't find one. Why does a carbocation accept an electron pair from a nucleophile and form a covalent bond rather than just accepting one electron like what happens between a sodium ion and a chloride ion in the formation of sodium chloride?


Some carbocations do form true ionic compounds. Many are known in which the positive charge is incorporated into an aromatic ring (e.g., cyclopropenyl, tropyl) or conjugated with multiple aromatic rings (e.g., triphenylmethyl). But in most carbocatioms you have a compact, relatively low-energy vacant orbital that will overlap to form a bond with an electron pair from, say, a chloride ion. Alkali metals don't have such compact valence orbitals and thus do not form a strong covalent bond even with the positive charge all on one atom.

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    $\begingroup$ You've reminded me that it's possible to make pure hydrocarbons which are actually ionic salts. Amazingly, these substances reversibly dissociate in organic solvents and their solutions conduct electricity! $\endgroup$ – Nicolau Saker Neto Oct 8 '17 at 0:05
  • $\begingroup$ I remember seeing those. They are awesome. Might they be better approaches to true, full-fledged ions than things like sodium chloride? $\endgroup$ – Oscar Lanzi Oct 8 '17 at 0:54
  • $\begingroup$ @OscarLanzi No, if you want as much ionic character as possible then check Non-coordinating anions. $\endgroup$ – Mithoron Oct 8 '17 at 13:37

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