halides

Easy....there are three ways this reaction can proceed.

I. The Grignard attacks the left C=O and transforms it into alcohol(with methyl attacking C).
II. GR attacks right C=O, but overall the same product forms.
III. GR attacks both C=O and hydrolysis yields a dihydric alcohol.

I and II cannot be separated by fractional distillation as they are basically the same. III can be separated from I/II.

So there are overall 3 products, two of which can be fractionally distilled and separated.

and maybe the third coz of Pinacol Pinacolone

Pinacol-pinacolone ke liye toh moderately acidic medium chaiye...whereas Grignard hydrolysis lightly acidic medium se bhi chal jaayega. Also you need to supply energy for the rearrangement and cation formation. Isliye I don't think pinacol reaction hoga(no heat given).
Nice thinking though Akshay...not everyone thinks that far ahead!