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Compound A is a chiral alkene of formula C6H12. The stereochemistry of A is R.

It undergoes hydroboration to give a chiral alcohol B of formula C6H14O. 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 C6H14.



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