AAMC 5 Organic Chem question

[misseskwee]

So this was a reaction in one of the passages. Basically they protect the C=O group in C-8 of the molecule so it doesn't react with the grignard in step 2 nor in the olefination in step 4. but my question is, how do you know the C=O group at C-1 won't be the one that will be converted to acetal and thus be the one protected? Just a general inquiry..

---

Members don't see this ad.

 

[MedPR]

Are you asking why only one carbonyl (C-8) gets protected while the other one doesn't? You've probably already realized it doesn't matter for this passage, but I don't know if there is a reason other than that's what they are telling you happens.

If anything, I assume the C-8 is more readily protected because there is less hindrance since it is further away from the bridgehead carbons.

 

[HollowSuperet36]

Yeah I dont think you complete that without a competing rxn happening.
It doesnt appear to be hindered a great deal.

But like MedPR said. Just take what they give you.

 

[misseskwee]

Are you asking why only one carbonyl (C-8) gets protected while the other one doesn't? You've probably already realized it doesn't matter for this passage, but I don't know if there is a reason other than that's what they are telling you happens.

If anything, I assume the C-8 is more readily protected because there is less hindrance since it is further away from the bridgehead carbons.

yes i'm simply just curious =)
It's not asked in any of the passage questions but just wanted to thoroughly get the entire process. Thanks! Makes sense.