Skip to content
Exercises · 7.10

Q.Why does R3P = O exist but R3N = O does not (R = alkyl group)?

Yanam BieapTextbookSubjectiveImportance★★★★★est
33% · 32/96 Questions
🔒 Locked · start free trial →

You're viewing a preview — the full solution, concept, methods & PYQ mapping are locked.

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 pπp\pi–dπd\pi back bond. Combined with the sigma bond, this gives R3P=OR_3P=O genuine double-bond character, so R3P=OR_3P=O (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 π\pi-donation from oxygen's p-orbital, so no true pπp\pi–dπd\pi N=O double bond can form.

Step 4: What nitrogen forms instead. …

Unlock everything free for 14 days

  • Full step-by-step solutions
  • Concept-first explanations
  • Methods, shortcuts & mistakes
  • PYQ mapping + timed mock tests

Full access for 14 days. No credit card required.