I came across a question that asked for a method to convert propene to glycerol. I used the method in the pic, but I'm worried about two steps-

Step-2, This reaction is just made up by myself! I'm using a 'bulky' base to favour elimination. Is this reaction feasible? Will it occur without giving any byproducts?

Step-3, Can I use MCPBA to convert an alkene containing an alcohol group to its corresponding epoxide? I'm worried that MCPBA can protonate the alcohol to generate the carbocation (moreover, the allylic carbocation makes it even more probable!) and that will lead to byproducts.

That's all.

Any help will be appreciated.


  • $\begingroup$ Step 2 is a known procedure run industrially by passing propylene oxide over a catalyst example here patents.google.com/patent/WO2017087479A1/en $\endgroup$
    – Waylander
    Jan 21, 2019 at 11:04
  • $\begingroup$ MCPBA is a pretty weak acid so I would not worry about the possibility of alcohol protonation. You could equally use the Sharpless procedure conditions - it did win a Nobel prize en.wikipedia.org/wiki/Sharpless_epoxidation $\endgroup$
    – Waylander
    Jan 21, 2019 at 11:05
  • $\begingroup$ @Waylander Okay! So step 2 is reasonable reaction. Am I right? $\endgroup$
    – Shivansh J
    Jan 21, 2019 at 11:06
  • $\begingroup$ @Waylander May I know the reason why MCPBA is a weak acid? Because it looks to me as a pretty strong acid because it has a carbonyl carbon withdraws electrons pretty well moreover it has a chloro group attached to benzene ring which enhances I- effect further. $\endgroup$
    – Shivansh J
    Jan 21, 2019 at 11:10
  • $\begingroup$ @Waylander Wow! It's a very weak acid. I saw its Pka value 7.57. Would love to know the reason why it is so. $\endgroup$
    – Shivansh J
    Jan 21, 2019 at 11:17


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