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Saturday, May 30, 2020

Why are bridge head carbocations unstable?

According to Bredt’s rule a bridgehead carbon atom of bicyclo compound cannot be sp2 hybridised or in other word a bridgehead carbon atom cannot be form double bond. unless the ring that contains at least eight atoms.

Related Questions:

Why is cyclopropyl methyl carbocation exceptionally stable?

The exceptional stability of cyclopropane methyl cation can be explained by the concept of dancing resonance concept. The stability of additional cyclopropyl group , is result of more conjugation between the bent orbital of cyclopropyl ring and cationic carbon.
The most stable carbocation known till date in organic chemistry is explain by Dancing resonance.
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Friday, May 29, 2020

Azabicyclo[2,2,1]heptane is more basic thantriethylamine why?.

1-Azabicyclo[2,2,1]heptane is more basic than triethylamine . Because in case of triethylamine the lone pair of electrons is less available in the latter due to rapid nitrogen inversion. Nitrogen inversion is not possible in the bicyclic amine.