Which of the two, Hydroxide anion OH- and Methoxide ion OCH3-, is a better nucleophile in aqueous medium?? I have 2 arguments both against each other. First, Oxygen atom in methoxide has higher negative charge density due +I effect of C atom, so methoxide should be the better nucleophile. Second, as methanol is a stronger acid than water, so OH- should be a stronger base, and hence OH- should be a better nucleophile. I was also thinking of solvation effect, like it happens in halogen family, which complicates the matter.


Your Answer

By clicking “Post Your Answer”, you agree to our terms of service, privacy policy and cookie policy

Browse other questions tagged or ask your own question.