Solving a Puzzling Chemistry Problem: What Went Wrong?

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The discussion revolves around understanding a chemical mechanism involving the movement of oxygen within a reaction. The original poster is confused about how an oxygen atom leaves and how to proceed after breaking apart a ring structure. A participant clarifies that the oxygen hasn't been lost but has shifted to a different carbon, resulting in a six-membered ring instead of a five-membered one. They suggest utilizing a catalyst in the initial step and experimenting with proton addition at various positions to explore potential products. The conversation emphasizes the importance of visualizing molecular changes to grasp the mechanism better.
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Homework Statement



2rr4dbp.jpg


Homework Equations





The Attempt at a Solution

This isn't really a homework problem but i'd like to know how to run this mechanism. I have no idea how one oxygen ended up leaving. I can make it so then the ring is broken apart and like turn the oxygen into a hydroxide...from then on out I'm confused as to wat to do...
 
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vipertongn said:

Homework Statement



2rr4dbp.jpg


Homework Equations





The Attempt at a Solution

This isn't really a homework problem but i'd like to know how to run this mechanism. I have no idea how one oxygen ended up leaving. I can make it so then the ring is broken apart and like turn the oxygen into a hydroxide...from then on out I'm confused as to wat to do...

You haven't lost oxygen. You have moved the etherial oxygen to a different carbon. This gives you a six-member ring instead of a 5-member one.

I find it useful to use the catalyst in the first step. Where would you add that proton so that it would give you a product? Do all three postitions and see where it leads...
 
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