Reaction scheme

I am supposed to find what X is. I know that $\ce{LiAlH_4}$ will convert all carbonyl groups to alcohols, and the ester group is being reduced. The only way of ending up with a ketone that I can think of is by a pinacol reaction.

However, the answer given was that X was $\ce{HOCH2CH2OH + H+}$. How does this work?

  • 3
    $\begingroup$ en.wikipedia.org/wiki/Protecting_group Read the introduction paragraph, it is exactly the same as your question. $\endgroup$ – orthocresol Dec 9 '15 at 5:22
  • $\begingroup$ That was helpful. $\endgroup$ – mathemather Dec 9 '15 at 5:24
  • 3
    $\begingroup$ By the way, you could technically use any alcohol you wanted to protect the ketone, although ethylene glycol is probably a reliable choice since you get the stability of a 5-membered ring. Basically, the answer isn't unique. $\endgroup$ – orthocresol Dec 9 '15 at 5:42

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.