[HaroTaro]

Would this simply be conversion into ketone? The ether on the left is really bothering me. Would there be the formation of ring structure?

[macman104]

It will breakdown the acetal protecting group on the left.  After oxidation of the alcohol on the right.

[HaroTaro]

I dont think it's a protecting group.

[macman104]

Why not?  You're going to get a diol and a mole of acetone, what's wrong with that?

[sjb]

Could you get some migration of the acetonide from the aldehyde to the ketone? (I don't think so, as the aldehyde is the more reactive of the two, but just trying to think out other possible products)

[macman104]

sjb, I don't see an aldehyde in the compound.

[sjb]

D'oh, think.. Grrr <censored>

[HaroTaro]

I wasn't sure because all the protecting group in the textbook looks like this....

[azmanam]

You might get some lactol formation (a cyclic hemiacetal) as a byproduct.

Or cross aldol with acetone?

[sjb]

Well, with that in mind, might you get the ketone protected by the diol itself?

[azmanam]

Interesting.  Something like this?  I hadn't thought of that.  It should be entropically favored, at least.

I don't see why it wouldn't happen.  It might be the favored product.  Good eye.

[Gregorian]

Interesting.  Something like this?  I hadn't thought of that.  It should be entropically favored, at least.

I don't see why it wouldn't happen.  It might be the favored product.  Good eye.

sorry this has nothing to do with the subject, but can you please tell me how you make the structures..  is it a program or what ? thank you

[azmanam]

chemdraw.

http://www.cambridgesoft.com/software/ChemDraw/

free versions are isisdraw

http://www.mdli.com/products/framework/isis_draw/index.jsp

or chemsketch

http://www.acdlabs.com/download/