Skip to content
Example · Example 11

Q.Explain why simple aliphatic amines such as CH3NH2\text{CH}_3\text{NH}_2 show optical inactivity even when nitrogen is bonded to three different groups plus a lone pair (four 'different' groups around nitrogen, as in a stereocentre).

West Bengal WbchseTextbookSubjectiveImportance★★★★★est
20% · 11/56 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 →

Formally, nitrogen in CH3NH2\text{CH}_3\text{NH}_2 (or any simple amine with three different substituents) does have four 'different' groups around it if the lone pair is counted as a group -- satisfying the geometric condition for a stereocentre. But unlike a carbon stereocentre, the pyramidal nitrogen can inter-convert its two mirror-image ('umbrella') forms by passing through a low-energy planar sp2sp^2 transition state, a process called nitrogen inversion that occurs extremely rapidly at room temperature (on the order of 101110^{11} times per second for a simple amine). The two enantiomeric forms interconvert far faster than they could …

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.