Could someone please help me figure out the products of the following reaction?
Here are few possibilities I've come up with:
The attacking reagent could the given vicinal diol, with its nucleophilic lone pair, attacking the electrophilic carbon of benzaldehyde. However, that doesn't seem to lead me anywhere.
As the reaction is carried out in acidic medium, one of the -OH groups (or both?) could be protonated, to become better leaving groups leading to formation of a carbocation intermediate. What after that?
Chances are it's probably a nucleophilic addition, proceeding through a tetrahedral intermediate, than a carbocationic one.
It'd be great if someone could show a proper mechanism for the reaction, and explain why it should be so. Thanks a lot!