Question

How many chiral centers are in testosterone?

Answer 1

There are six chiral centres in testosterone.

Explanation:

The structural formula of testosterone is

There are no internal mirror planes, so every carbon atom is different.

Here is how the carbon atoms are numbered.

Using these numbers, the chiral carbon atoms in testosterone are `8, 9, 10, 13, 14`, and `17`.

The jaw-breaking IUPAC name gives the configuration at each of these centres:

(`8R,9S,10R,13S,14S,17S`)- 17-hydroxy-10,13-dimethyl- 1,2,6,7,8,9,11,12,14,15,16,17- dodecahydrocyclopenta[a]phenanthren-3-one.