Is protected carbonyl group a electron donating group?

[nickh]

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Hey guys,

So I know you once you protect a carbonyl group with HOCH2CH2OH, it becomes an o/p director. But I'm just wondering does the extra carbons make it an electron donating group as well? Or is it just acting like a halogen where it's an o/p director but it's still electron withdrawing?

Thanks again for all the help! 🙂

 

[kholley25]

I believe the oxygens from the diol would donate electrons similar to that of an ether. Someone correct me if I'm wrong.

 

[DAT Destroyer]

I believe the oxygens from the diol would donate electrons similar to that of an ether. Someone correct me if I'm wrong.

Fantastic answer!

This is often a very useful procedure in organic synthesis when we transform a meta director into an o/p director. Just think of a protecting group as a "double" ether.