# Rate of solvolysis of allyl and alkyl halides

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.

• 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. – Manu Jul 1 '20 at 15:50
• 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/… – Aniruddha Deb Jul 1 '20 at 17:25
• 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 – Charlie Jul 2 '20 at 8:16