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I underestimated this question and just compared the carbocation stability of all the compounds (after removal of chloride via $S_N1$) and got the order D>C>B>A... but my answer is incorrect, what am I missing out?

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    $\begingroup$ Can't we bend the ring and bring that O closer, so as to have some intramolecular stabilization? $\endgroup$ – Ivan Neretin Feb 7 '18 at 8:48
  • $\begingroup$ Is the answer A>B>D>C , if it is then I'll provide my reasoning . If it's not then I'll wait for the question to get answered. $\endgroup$ – Avyansh Katiyar Feb 7 '18 at 8:50
  • $\begingroup$ @AvatarShiny I don't know the correct order but C has the fastest solvolysis rate $\endgroup$ – Carrick Feb 7 '18 at 12:24
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    $\begingroup$ Bringing O closer does not make its -I more intense. -I spreads along sigma bonds, roughly speaking. $\endgroup$ – Ivan Neretin Feb 7 '18 at 12:44
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    $\begingroup$ -I does not care about distance. What it cares about is the number of bonds between O and (+). $\endgroup$ – Ivan Neretin Feb 7 '18 at 13:15
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The rate of solvolysis is highest in (C) as a 6 membered ring is formed which is more stable than 4 & 5 membered rings.

And (B) more readily formed than (D) because the NGP ability of oxygen is more than that of an alkene(due to high charge density of oxygen).

So the correct order is C>B>D>A.

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  • $\begingroup$ Well this question was easy and I have no idea why I couldn't possibly answer it earlier...thank you everyone for still paying attention $\endgroup$ – Carrick Feb 7 '18 at 17:21
  • $\begingroup$ And here I thought to tell you to be careful with answering. This is not how NGP works; neighbouring groups stabilize cation by binding to it. Read your textbook again. $\endgroup$ – Mithoron Feb 7 '18 at 17:37

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