Example · Example 11
Q.Explain why simple aliphatic amines such as 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).
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Start your 14-day free trial to unlock the full solution →Formally, nitrogen in (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 transition state, a process called nitrogen inversion that occurs extremely rapidly at room temperature (on the order of times per second for a simple amine). The two enantiomeric forms interconvert far faster than they could …
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