Question

How many diastereoisomers does cocaine have? List them.

Answer 1

As a general rule:-When more than one chiral center is present in the molecule, the yield of stereoisomers is 2 to the power n, where "n" is the number of chiral centers. Half of the pairs are enantiomers, and the other half are diastereomers.Diastereomers have the same structural formula but will usually exhibit different physical, chemical and pharmacological properties. (examples: pseudococaine, allococaine and allopseudococaine).Cocaine has 4 stereocentres (chiral centres) and 16 possible optical isomers.The bridge does not affect the number ofstereoisomers.