Thursday, January 31, 2013
Epoxide sapling question
I was having a little trouble with sapling problem #17 which is an epoxide reacting with H2O and Hydronium. After reading the section in chapter ten I did work it out and get the right answer but im not positive about the mechanism, I just kinda guessed it would add another alcohol group given the reactants and got lucky. I think the H3O protonates the oxygen, then from there I have some ideas, but if anyone knows for sure how that mechanism works I would appreciate any response.
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Yes, H+ will protonate the the oxygen of the epoxide first. Water can actually open the epoxide ring at that point because protonated epoxides can be opened by poor nucleophiles. Check out the example on pg. 432--it's a similar mechanism. I also posted a link below for how I would approach the problem.
ReplyDeletehttps://www.evernote.com/shard/s260/sh/af27a4c6-c4ca-462f-9055-956937318443/b29c4a598de88c83024f91de8092115b