[BabeToluene]

Hey, guys!

I'm trying to understand the regio- and stereochemistry of the products that would form when the below reaction occurs and why they happen that way. So far, I'm convinced that there can be a case where the -OH points out of the page while the -CH3 and -Br point into the page. Is there anything else that can be displayed in the product?

Please post any of your thoughts and explanations. Thanks.

[bolo]

Look at the TS where water as a weak nucleophile approaches C1 from the opposite side to brominium cation. It is because of more stable 3^o pseudo-carbocation (C1) rather than 2^o C2.



Finally you are obtained with two enantiomers of product.

[BabeToluene]

Hmm. Based on your picture, are you saying that the Br was connected to C1 and C2 throughout some part of the mechanism? That would explain why they either both point out or both point in, opposite to the -OH.

[bolo]

Yes. It is said to exist two enantiomeric forms of brominium ion and then an nuclophilic attack on 3^o carbon occurs. It is somehow similar to ring opening of aziridines.

[BabeToluene]

I see it now. Thank you both for your help.