0
$\begingroup$

Why strong bases only give elimination products as major while they could give substitution products too being good nucleophiles? (I am excluding those non nucleophilic bases)

$\endgroup$
3
  • $\begingroup$ This is an awfully general statement... $\endgroup$
    – Zhe
    Commented May 27, 2020 at 18:45
  • $\begingroup$ You might want to look into HSAB theory. Generally, a saturated carbon centre is a 'soft' electrophile, while an acidic proton is a 'hard' electrophile. This can be the difference in reactivity of certain nucleophiles. $\endgroup$
    – Jabbamanga
    Commented May 27, 2020 at 18:52
  • $\begingroup$ As what Zhe mentioned, the statement you are making seems to be overly general. Substitution and elimination are in competition and the ratio of the two reactions depends on not just the strength of the reagent as a nucleophile or base but also, on the solvent and temperature. E.g. Hydroxides may seem like a good base and nucleophile but their reaction with alkyl halides differ based on other conditions. Generally, $\ce {KOH}$ in ethanol at high temperature would favour elimination for primary alkyl halides while aqueous $\ce {KOH}$ at lower temperatures may favour dominance of substitution. $\endgroup$ Commented May 28, 2020 at 11:57

0

Your Answer

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

Browse other questions tagged or ask your own question.