Stereocenter vs. Chiral Center

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  • 0:04 The Shape of a Hand
  • 0:27 Stereocenters
  • 1:17 Chiral Centers
  • 2:01 Applications
  • 2:55 Lesson Summary
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Lesson Transcript
Instructor: Allyn Torres

Allyn has taught high school chemistry, and has a master's degree in curriculum and instruction.

Learn about stereocenters and chiral centers in molecules in this lesson. We'll talk about the similarities and differences as well as a tragic consequence of one real-world application.

The Shape of a Hand

Have you ever thought about how weird it would be if both of our hands were exactly the same? It would probably change how we do everyday tasks and might even make some things easier. No longer would we have to worry about which glove we were putting on which hand. It wouldn't matter! The fact is, however, that our hands aren't identical to each other. They're chiral (more on that later). Molecules can be chiral, too.

Stereocenters

A stereocenter is not a store where you can buy stereos, even though that's definitely what it sounds like. A stereocenter occurs in a molecule when a carbon atom is connected to three or more other atoms or atom groups. The key here is that each of the three groups or atoms connected to the central atom need to be different from each other. For example, a carbon atom connected to a CH3 group, a CH2 CH3 group, and a CH2 CH2 CH3 group is a stereocenter.

As is common in organic chemistry, every ''point'' in the structure is representative of a CH2 connection and every end point is a CH3 connection.

The different rearrangement of groups around a stereocenter result in stereoisomers. Stereoisomers are two or more molecules that are made of the same atoms and groups, but the groups are arranged differently.

Chiral Centers

A chiral center occurs when a carbon atom is connected to four different atoms or groups. Like stereocenters, in order for a chiral center to occur, the groups must all be different from one another. An example of a chiral center is a carbon atom attached to a chlorine atom, a bromine atom, a hydrogen atom, and a fluorine atom. Note that by definition, chiral centers can be considered stereocenters, but stereocenters are not always chiral centers.

Chiral centers result in chiral molecules. Chiral molecules have the same groups within them, but are mirror images of each other: they won't match up when laid on top of each other. The word chiral comes from the Greek word kheir, which means ''hand.'' Both our hands and feet are in fact chiral.

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