Regarding this reaction, other than de-protecting the acetal, will we have an elimination reaction for the alcohol or no?

enter image description here

  • 3
    $\begingroup$ Base is of no relevance here. It depends entirely on how strong the acid conditions are. It is easy to select conditions that will deprotect without elimination though you could easily form the hemi-acetal of the ketone. $\endgroup$
    – Waylander
    May 17 '19 at 14:52
  • $\begingroup$ You can't eliminate hydroxyl groups with base $\endgroup$
    – orthocresol
    May 17 '19 at 15:02
  • 1
    $\begingroup$ Welcome to Chemistry.SE! We have a site policy for homework questions. Please edit your question to include your attempt at the problem, where you got stuck, and let us know where you're finding difficulty so we may best help you. $\endgroup$
    – Melanie Shebel
    May 18 '19 at 8:44

As I said in the comments, it entirely depends on the conditions. It is easy to select mild conditions to cleave the dioxolane. Elimination would require very strong forcing conditions (concentrated acid and heating). The first site of protonation is the carbonyl, so you would form the hemi-acetal of the product long before elimination or substitution occured at the primary alcohol. If you were foolish enough to heat this with cH2SO4 then you could get elimination of the primary alcohol and generate quite a mess.


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.