Stereochemistry: Identifying Stereocenters

Exercise Solutions

Stereocenters are indicated with an arrow.

c. Even though both carbon chains are five atoms, the fact that one is linear and the other branched makes them different. Thus the carbon bearing the hydrogen, iodine and two different five-carbon chains is a stereocenter.

The carbon bearing the SH group is not a stereocenter because the four attachments (SH, CHOH, and two methyl groups) are not all different.

This molecule does not have any atoms with four different attachments, so it does not have any stereocenters.

The nitrogen atom is a stereocenter because it has four different attachments: CH₃, two different CH groups, and a lone pair.

Link to:

Identifying Stereocenters Tutorial and Exercises
Tutorial Topic List
Stereochemistry Practice Problems