SN1 reactivity order for chloromethyl methyl ether and trityl chloride


> 
> Compare the reactivity order towards SN1 reaction for: 
> 
> 
> 1. (2-chloropropan-2-yl)cyclopropane
> 2. $\ce{CH3OCH2Cl}$
> 3. $\ce{Ph3CCl}$
> 
> 
> 


Owing to the exceptional stability of cyclopropyl ethyl carbocation ([see](https://chemistry.stackexchange.com/questions/19090/what-is-the-reason-for-the-exceptional-stability-of-the-cyclopropylmethyl-carboc)), obviously it should be on the top.


We did this question in class and my teacher told me that option 2 is more reactive than option 3, because the carbocation formed in the case of 2 is more stable. However, I couldn't quite understand the reason for it. 


Anyway, I searched more for this and found the following table in March's 7th edition, page 425: 


[![enter image description here](https://i.stack.imgur.com/qusj4.png)](https://i.stack.imgur.com/qusj4.png)


According to this table $\ce{Ar3CX > CH3OCH2X}$ in terms of reactivity towards SN1.


Today, I went to my teacher with this data and asked him about it. He told me that things in March can be wrong sometimes, I should rather check some other sources and prove it to him. 


So I'd like to know what is the actual order, is 2 more reactive than 3, or vice-versa? (please mention your source) And why?


I have also checked Peter Skyes' and Morrison Boyd's, Clayden's book but it's not given there. 




---


This issue has been discussed [previously on the site](https://chemistry.stackexchange.com/questions/34381/sn1-reactivity-order?rq=1#comment52424_34381) but no *concrete conclusion* has been reached. 


[Jan's answer](https://chemistry.stackexchange.com/a/38143/51553) *suggests* that $\ce{CH3OCH2Cl}$ should be more reactive than trityl chloride.


