Chapter Contents
- 5.1 Enantiomers and the Tetrahedral Carbon
- 5.2 The Reason for Handedness in Molecules: Chirality
- 5.3 Optical Activity
- 5.4 Pasteur’s Discovery of Enantiomers
- 5.5 Sequence Rules for Specifying Configuration
- 5.6 Diastereomers
- 5.7 Meso Compounds
- 5.8 Racemic Mixtures and the Resolution of Enantiomers
- 5.9 A Review of Isomerism
- 5.10 Chirality at Nitrogen, Phosphorus, and Sulfur
- 5.11 Prochirality
- 5.12 Chirality in Nature and Chiral Environments
Why This Chapter?
5 • Why This Chapter?
Understanding the causes and consequences of molecular handedness is crucial to understanding organic and biological chemistry. The subject can be a bit complex at first, but the material covered in this chapter nevertheless forms the basis for much of the remainder of the book.
Are you right-handed or left-handed? You may not spend much time thinking about it, but handedness plays a surprisingly large role in your daily activities. Many musical instruments, such as oboes and clarinets, have a handedness to them; the last available softball glove always fits the wrong hand. The reason for these difficulties is that our hands aren’t identical; rather, they’re mirror images. When you hold a left hand up to a mirror, the image you see looks like a right hand. Try it.
Handedness is also important in organic and biological chemistry, where it arises primarily as a consequence of the tetrahedral stereochemistry of sp3-hybridized carbon atoms. Many drugs and almost all the molecules in our bodies—amino acids, carbohydrates, nucleic acids, and many more—have a handedness. Furthermore, molecular handedness enables the precise interactions between enzymes and their substrates that are involved in the hundreds of thousands of chemical reactions on which life is based.