Question
Chemistry Question on Organic Chemistry- Some Basic Principles and Techniques
Which amongst the following is the most stable carbocation?
+CH3
CH3CH3+
Solution
The most stable carbocation is t-alkyl carbocation because the order of stability of alkyl carbocation is t-alkyl >s-alkyl> p-alkyl *> CH3 carbocation. This stability order is described with the help of hyperconjugation and inductive effect. On the basis of hyperconjugation, (CH3)2CH+ CH shows six resonating structures due to the presence of six a-C - H bonds, Greater the α H-atom greater will be the hyper conjugation resonating structure and therefore, greater will be the stability. CH3+does not show the property of resonance while CH3−+CHshows three resonating structures due to presence of three a-C - H bonds. Hence, larger number of resonating structures are possible in (b), so it is most stable. The above order of stability is also explained with the help of (+) /-effect of -CH3 group. More the number of - CH3 group more will be tendency to displace the electrons towards positive charged carbon of carbocation. Thus, positive charge is decreased or compensated and stability of carbocation is increased.