2
$\begingroup$

My book reads

Sulphonation will be the most effected electrophilic aromatic substitution reaction when benzene is replaced by hexadeutrobenzene.

I am not able to figure out how. All EAS reactions proceed by formation of an arenium ion and then the loss of an $H^+$ ion to regain aromaticity so all of them should be equally effected ( textbook does not mention how they are effected). I feel the only effect should be due to difference in bond enthalpies of $C-D$ bond and $ C-H$ bond.

I came across this reaction mechanism from chemlibretexts: enter image description here The hydrogen released is taken up by the $-SO_3H^-$

Can someone explain how and in what ways the replacement of hydrogen by deuterium effects the reaction ?

Improve this question
$\endgroup$
1
  • $\begingroup$ Noting edits is not necessary. Anyone can see the edit history. $\endgroup$
    – A.K.
    Apr 4, 2019 at 15:43

0

Reset to default

Your Answer

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