1
$\begingroup$

Suppose I have 2 compounds, 3-chloropropene and 1-bromo-1-methylcyclohexane. Without knowing the values, how can we compare the rate of solvolysis?

My attempt: Resonance is quite dominant character thus alkyl chloride resonance I think should dominate over hyperconjugation but then we have an exception that 3 degree carbocation is more stable than benzyl carbocation hence there might be some disparity in orders.

$\endgroup$
3
  • $\begingroup$ Resonance effect is more stronger than hyperconjugation irrespective of the number of $\alpha$H. In first case allylic carbocation is formed which is stabilised by resonance. So solvolysis rate is more for the first compound. $\endgroup$ – Manu Jul 1 '20 at 15:50
  • $\begingroup$ 3 degree carbocation is more stable than benzyl carbocation - only for trimethyl carbocation; other 3 degree carbocations are less stable than benzyl carbocation. See chemistry.stackexchange.com/questions/74943/… $\endgroup$ – Aniruddha Deb Jul 1 '20 at 17:25
  • $\begingroup$ Now problem is that in answer of this question they have given the reverse order but I think concepts matter more so what is reality that should be right answer. Thanks $\endgroup$ – Charlie Jul 2 '20 at 8:16
0
$\begingroup$

Resonance effect is more stronger than hyperconjugation irrespective of the number of αH. In first case allylic carbocation is formed which is stabilised by resonance. So solvolysis rate is more for the first compound

$\endgroup$

Your Answer

By clicking “Post Your Answer”, you agree to our terms of service, privacy policy and cookie policy

Not the answer you're looking for? Browse other questions tagged or ask your own question.