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Chirality is an important spatial property of a single organic molecule, but organic chemists often think about the spatial relationships between two or more molecules as well. For example, we can characterize two molecules as enantiomeric if they are mirror images but not identical. Diastereomers have the same connectivity, but are not identical and are also not mirror images.

Read about enantiomorphism here and diastereomorphism here. Use the examples on these pages to both identify the stereocenters within each molecule and find instances of enantiomorphism and diastereomorphism. Think about how you might use the numbers and types of stereocenters within a particular molecule to predict how many enantiomers and diastereomers it has.

Synthesizing a chiral molecule from achiral precursors, without creating its enantiomer at the same time, happens to be a very difficult task. Many organic chemists have dedicated their careers to developing reactions that accomplish this goal. Check out the Wikipedia article on enantioselective synthesis to explore some methods chemists have used to create enantiopure, chiral compounds from achiral starting materials.

One useful method for the isolation of a single enantiomer involves the separation of a mixture of enantiomers, a process called resolution. Read about resolution here, and describe in your own words how introducing a pure enantiomer of a different molecule can help separate a mixture of enantiomers.

Enantioselective Synthesis, from Wikipedia http://en.wikipedia.org/wiki/Enantioselective_synthesis

The Virtual Textbook of Organic Chemistry http://www2.chemistry.msu.edu/faculty/reusch/VirtTxtJml/

IUPAC’s Basic Terminology of Stereochemistry http://www.chem.qmul.ac.uk/iupac/stereo/

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