If I have an alkyl halide, in which its tertiary carbon is non-chiral (for example 2-bromobutane), which reacts via an SN1 mechanism does it also produce 2 products?

I am asking because I know that the carbocation intermediate's plane of symmetry allows the nucleophile to attack equally well from either side and thus the product is a racemic mixture of enantiomers. Is this also the case for a non-chiral substrate?

  • $\begingroup$ @H.Linkhorn We prefer to not use MathJax in the title field, see here for details. $\endgroup$ – Martin - マーチン May 18 '19 at 19:01
  • $\begingroup$ The formation of the product will happen along both pathways, but since the product is as achiral as the reactant, you won't find different products, and you can't tell. $\endgroup$ – Martin - マーチン May 18 '19 at 19:05
  • 1
    $\begingroup$ Not sure what you mean here; 2-bromobutane is undoubtedly chiral (we even have a question on it). If you mean something like 2-bromopropane, or 3-bromopentane, then Martin's comment is spot on. $\endgroup$ – orthocresol May 18 '19 at 19:54
  • $\begingroup$ You are asking about a non-chiral substrate, but the example you chose is chiral. Which case are you asking about? Could you edit your question accordingly? $\endgroup$ – Karsten Theis May 18 '19 at 23:51
  • $\begingroup$ I am sorry, I meant 2-bromo-2-methylpropane. I edited it out. I must have confused it with another substrate I was looking at. $\endgroup$ – baraah baryhe May 19 '19 at 8:48

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.