Stereoisomerism and Chirality Review

These flashcards cover key terminology and concepts related to stereoisomerism and chirality, essential for understanding the structural aspects of organic chemistry.

Stereoisomerism

Isomers with the same connectivity but different spatial arrangements.

Chirality

A property of a molecule that makes it non-superimposable on its mirror image.

Enantiomers

Stereoisomers that are mirror images of one another but not superimposable.

Diastereomers

Stereoisomers that are not mirror images of one another.

Cis-Trans Isomerism

A type of stereoisomerism where substituents differ in orientation about a double bond or ring structure.

R/S Configuration

A system used to describe the spatial arrangement of groups around a stereogenic center.

Chirality Center

A carbon atom bonded to four different groups, thus giving rise to chirality.

Meso Compound

A compound with multiple stereogenic centers that has a plane of symmetry, making it achiral.

Optical Activity

The ability of a chiral compound to rotate plane-polarized light.

Cahn-Ingold-Prelog Priority Rules

Rules used to assign priority to groups attached to a stereogenic center for R/S configuration assignment.

Superimposable

When two objects can be placed over one another and match exactly.

Achiral

An object or molecule that is identical to its mirror image.

Chiral Molecule

A molecule that is not superimposable on its mirror image.

E/Z Nomenclature

A system used for determining the geometry of alkenes based on the highest priority substituents.

Enantiomeric Excess (ee)

A quantitative measure of the purity of one enantiomer in a mixture.

Optical Purity

The measurement of the excess of one enantiomer over the racemic mixture.

Fischer Projection

A two-dimensional representation of three-dimensional organic molecules.

Conformational Mobility

The ability of a molecule to adopt different configurations due to rotation around single bonds.

Atropisomers

Stereoisomers that arise from restricted rotation about a single bond.

Meso Compound Characteristics

Achiral, has multiple stereogenic centers, and possesses a plane of symmetry.