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Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: Susuman on July 18, 2017, 09:37:37 AM

Title: How should the electrons mechanism look?
Post by: Susuman on July 18, 2017, 09:37:37 AM

Hello guys,
I'm trying to solve a problem of "draw the electron mechanism that brings this product from X".
(https://snag.gy/4Qla58.jpg)
Beside knowing it's probably an E1 mechanism with an acid that should contain a carbocation, I'm quite clueless about how to start. Any idea how do I turn the OH into a ring expansion and a double bond?
Thanks.

Title: Re: How should the electrons mechanism look?
Post by: Arkcon on July 18, 2017, 11:20:10 AM

OK.  Let's work with what we have.  (BTW, I'm awful at Organic chemistry, so take my advice with a grain of salt until an expert weighs in.)  You add acid, H+.  The molecule on the right lacks an OH, where did it go, and what did it make, and what was left.  And are you sure, E1 would be favored, in this case?  https://en.wikipedia.org/wiki/Elimination_reaction#E1_mechanism

Title: Re: How should the electrons mechanism look?
Post by: Babcock_Hall on July 18, 2017, 12:04:19 PM

If you add a proton to a hydroxyl group, does it become a better leaving group or a worse leaving group?