-2
$\begingroup$

In Alcohols(secondary,tertiary,benzylic,allyic) on reaction with HX, X=(Cl,Br,I) SN1 takes place as H2O leaves and forms a carbonation.But in ethers on reaction with HX, X=(Cl,Br,I) (except tertiary,benzylic) SN2 takes place. Is ROH not as good leaving group as H2O.what is the reason for SN1 in Alcohols and SN2 in ethers??

$\endgroup$

1 Answer 1

0
$\begingroup$

From what I understand, the generalization you have constructed is not based on any gross rule that - "ROH not as good leaving group as H2O". I think what you mean is that the protonated alkoxy group is a poorer leaving group than the OH2+ group, in which case I would still not agree to a generalization unless I know the identity of the R group. There are many ethers that show SN1 substitution reactions as well, especially under acidic conditions. A good example is the highly strained oxirane ring, which opens via an SN1 reaction in low pH.

$\endgroup$
1
  • $\begingroup$ Solvation of the leaving group is important. an ether under SN1 conditions will be less efficiently solvated $\endgroup$
    – jimchmst
    Commented Dec 8, 2022 at 23:04

Your Answer

By clicking “Post Your Answer”, you agree to our terms of service and acknowledge you have read our privacy policy.

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