"(3R,6R)-6-Bromo-3-octanol (A) is expected to form optically inactive B (C8H16O) upon exposure to aqueous NaOH. A stereoisomer of A, namely, C also forms B under the same conditions. Two other stereoisomers of A, namely D and E as a 50/50 mixture, form optically inactive F, a diastereoisomer of B. What are the structures of A-F? The structures D and E are not distinguishable. Explain and illustrate with mechanisms."
I hope I am not breaking any rules here, but apart from coming up with the structure for A, I can't get much further. I still do not understand what happens to the OH- from the NaOH.