Q.Why does R3P = O exist but R3N = O does not (R = alkyl group)?
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Start your 14-day free trial to unlock the full solution →Step 1: Bonding requirement for a true E=O double bond.
A genuine double bond between the central atom E and oxygen requires, in addition to the sigma bond, a pi bond formed by overlap of a filled p-orbital on O with an empty, appropriately-oriented orbital on E.
Step 2: Phosphorus's case.
Phosphorus (period 3) has empty, energetically accessible 3d orbitals in its valence shell. A filled p-orbital on oxygen can donate electron density into an empty 3d orbital on phosphorus, forming a – back bond. Combined with the sigma bond, this gives genuine double-bond character, so (e.g. phosphine oxides) exist as stable, well-characterised compounds.
Step 3: Nitrogen's case.
Nitrogen (period 2) has no d-orbitals in its valence shell (only 2s, 2p are available, all used up in bonding/lone pair). It cannot accept a -donation from oxygen's p-orbital, so no true – N=O double bond can form.
Step 4: What nitrogen forms instead. …
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