Which halogenoalkane reacts fastest with sodium hydroxide?

A. 1-iodobutane B. 1-chlorobutane C. 2-chloro-2-methylpropane D. 2-iodo-2-methylpropane

Iodine has a larger radius, thus less electronegative making it a better leaving group. And since OH is a protic substance it favors Sn1, which is a tertiary, so the answer must be d... but it says that the answer is b.. how????

  • 2
    $\begingroup$ As others have noted below, this seems line an $S_{N}2$ reaction and iodine is an excellent leaving group, so the answer seems to be "A". Let us know if you hear back about why "B" is correct or if the answer key was in error. $\endgroup$
    – ron
    Apr 28 '17 at 17:47

Yes iodine's good leaving group. the leaving ability is best described by the Gibbs energy change that occurs.

So since chlorine is a poor leaving group so that make the reaction slower as less energy is available. So I think that you are right so far.

  • 1
    $\begingroup$ Iodide is a much better leaving group than chloride. $\endgroup$
    – orthocresol
    Feb 27 '17 at 17:15
  • $\begingroup$ ohh! sorry about that I just thought the reverse case ; $\endgroup$ Feb 27 '17 at 17:18
  • 3
    $\begingroup$ Also, this looks like a better candidate for $\mathrm{S}_{N}2$ chemistry... $\endgroup$
    – Zhe
    Feb 27 '17 at 17:44

Your Answer

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

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