Why is a protected carbonyl group an Ortho/Para director?

[FutureDDS_11]

(see attached)
I am having trouble comprehending one problem on a practice exam. It starts with the carbonyl substituent of a benzene undergoing HOROH, H+ to make a protected carbonyl group. Then they added Cl2, FeCl3. I expected the substituent to act as a meta director, because the carbon directly attached to the benzene is attached to two oxygens, thus would still be slightly positive and would still act as a meta director the same way that a regular carbonyl carbon would. However, the solution says that it acts as an ortho/para director.

Can someone explain why?

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[Likkriue]

That group over there acts like two methoxy groups. Remember anisole directs ortho para because it donates electrons and forms resonance. The protecting group, forgot what it's called, does the same thing.

 

[Dawgsby90]

Oxygen (non carbonyl) and carbon are considered Electron donating groups (EDG) and are more activating species, meaning ortho/para as opposed to a carbonyl which is a deactivating (Meta). The purpose of protecting the carbonyl is to be able to control your aromatic addition. This is common on the DAT

 

[FutureDDS_11]

Thank you both for the quick reply, I understand the OR is a donating group (also ortho/para director) but I can't understand how the -C(OR)2 acts the same way, because wouldn't that directly attached carbon still be slightly positive and still be withdrawing?

 

[FutureDDS_11]

I'm bumping this because I am still unsure about this problem
@orgoman22 Dr. Romano can you please explain?

 

[DAT Destroyer]

(see attached)
I am having trouble comprehending one problem on a practice exam. It starts with the carbonyl substituent of a benzene undergoing HOROH, H+ to make a protected carbonyl group. Then they added Cl2, FeCl3. I expected the substituent to act as a meta director, because the carbon directly attached to the benzene is attached to two oxygens, thus would still be slightly positive and would still act as a meta director the same way that a regular carbonyl carbon would. However, the solution says that it acts as an ortho/para director.

Can someone explain why?

This group is an ACETAL group.....think of it as an OR group.....a very good para director !!!! In the Real World......this would be a great way to add to the para position. The original group was a meta director...this functionality changed the directing influence !!!! Hope this helps.