Compound A is a chiral alkene of formula C
6H
12. The stereochemistry of
A is
R.
It undergoes hydroboration to give a chiral alcohol
B of formula C
6H
14O. Oxymercuration of
A gives a pair of alcohols, C
(1) and C
(2), that are chiral and stereoisomers of each other. Sulfuric acid catalysed addition of water to
A gives a third alcohol
D of the same formula, but it is achiral. Finally, palladium catalyzed hydrogenation of
A gives an achiral alkane of formula C
6H
14.