Sample NMR hydrobenzoin and hydrobenzoin acetal (not available for submission for credit)
Stock IR Benzoin (for reference)
Stock IR 1,2-diphenyl-1,2-ethanediol (available for submission for credit, see laboratory manual for details)
Stock FID 1H-NMR 1,2-diphenyl-1,2-ethanediol acetal (available for submission for credit, see laboratory manual for details)
A1) In order to understand the stereochemical outcome of this experiment, it is critical to have the basic terminology correct. A short review of the issues is available.
A2) One of the easiest ways to understand how the acetal products may differ in the 1H-NMR spectra is to build a model of each and look at the relative positions of each 1H-atom in each structure. If the molecular structure around the 1H-atoms is the same, or can be conformationally exchanged, then those 1H-atoms will have the same chemical shift and will be equivalent in 1H-NMR spectroscopy.
A handout with an example thioacetal has been prepared showing how these issues work in an actual molecule.