Orgoreview

Compounds A and B are alkenes of formula C₆H₁₂. Upon hydrogenation, alkenes A and B give the same compound. Upon addition of HBr, alkenes A and B give the same compound that can be converted back to A with sodium hydroxide.  Bromination of A gives a single compound C. Dihydroxylation of B with osmium tetroxide gives a pair of enantiomers. Ozonolysis of A gives a single compound. Ozonolysis of B gives two compounds.



Draw structures of A, B, C, and D showing the proper stereochemistry of each molecule.