Which of the following is not an electrophile ?
Na+
The sodium ion is not an electrophile — option 1.
What an electrophile is. The word means “electron-loving”. An electrophile is a species that is electron-deficient and that attacks a region of high electron density, accepting a pair of electrons to form a new covalent bond. It is therefore a Lewis acid. The last part of that definition is what matters here.
| Species | Electron count | Electrophile ? |
|---|---|---|
| Na+ | 2, 8 — a complete noble-gas octet | No — it is already stable and forms ionic, not covalent, bonds |
| BF3 | Boron has only 6 electrons — an incomplete octet | Yes — the classic neutral electrophile and Lewis acid |
| H+ | Zero electrons — a bare proton | Yes — the simplest electrophile of all |
Why a positive charge is not enough. This is the point of the question. Na+ carries a full positive charge and is therefore attracted to negative charge — but attraction is not the same as bonding. Having achieved the neon configuration by losing its single valence electron, sodium has no vacant low-energy orbital in which to accept a pair, and the compounds it forms are held by electrostatic attraction between ions. In solution it is a spectator ion: in a reaction such as
\(\text{NaOH}+\text{HCl}\rightarrow\text{NaCl}+\text{H}_{2}\text{O}\)
the sodium ion takes no chemical part at all. The same is true of K+, Mg2+ and Ca2+.
The contrast. BF3 and H+ both have somewhere to put an incoming pair — an empty p orbital on boron, an empty 1s orbital on the proton — and both form covalent bonds by accepting one. Other common electrophiles are the nitronium ion NO2+ in nitration, AlCl3 in Friedel-Crafts reactions, carbocations, and the carbon of a carbonyl group.
The counterpart is the nucleophile — electron-rich, a Lewis base, which donates a pair: OH−, CN−, NH3, water.
Hence, the answer is Na+.
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