(a) Based on the following information, draw three-dimensional formulas for A, B, and C.
Reaction of cyclopentene with bromine in water gives A,
Reaction of A with aqueus NaOH (1 equivalent, cold) gives B, C5H8O (No 3590-3650-cm-1 infrared absorption).
Heating of B in methanol containing a catalytic amount of strong acid gives C, C6H12O2, which does show 3590-3650-cm-1 infrared absorption.
(b) Specify the (R) or (S) configuration of the chirality centers in your predicted structures for C. Would C be formed as a single stereoisomer or as a racemate?
(c) How could you experimentally confirm your predictions about the stereochemistry of C?