Solving a Puzzling Chemistry Problem: What Went Wrong?

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Homework Statement



Reaction scheme: a five-membered cyclic ether with a CH2OH side chain and an OH group converts under Acid, arrow to a six-membered cyclic ether with HO and OH substituents. Text reads: 3. Draw the mechanism. Which direction (forward vs. reverse) is more favored and why?


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...
 
vipertongn said:

Homework Statement



Homework question 3 asking to draw the mechanism and state whether the forward or reverse direction is favored, with a reaction arrow labeled Acid converting a five-membered cyclic ether bearing a CH2OH side chain and an OH group into a six-membered cyclic ether with OH groups.


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...