Chapter 5: Chirality and Stereochemistry

This set of flashcards covers key vocabulary and concepts associated with chirality and stereochemistry in organic chemistry.

Enantiomers

Molecules that are non-superimposable mirror images of each other.

Chiral

A molecule that cannot be superimposed on its mirror image and lacks a plane of symmetry.

Achiral

A molecule that can be superimposed on its mirror image and has a plane of symmetry.

Stereoisomers

Compounds that have the same molecular formula and connectivity but differ in spatial arrangement.

Optical Activity

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

Dextrorotatory

A substance that rotates plane-polarized light to the right.

Levorotatory

A substance that rotates plane-polarized light to the left.

Diastereomers

Stereoisomers that are not mirror images of each other.

Prochirality

A property of a molecule that can become chiral in a single chemical transformation.

Meso Compound

A compound with multiple chiral centers that is superimposable on its mirror image due to internal symmetry.

Racemic Mixture

An equal mixture of two enantiomers which is optically inactive.

Cahn–Iнгold–Prelog Rules

A set of rules used to assign priorities to substituents attached to a chiral center.

Chirality Center

An atom, usually carbon, that is attached to four different substituents.

Epimer

A type of diastereomer that differs from another isomer in the configuration at only one chiral center.

Chirality at Nitrogen

Refers to the potential chiral nature of nitrogen compounds, although they often invert rapidly.

Chiral Environment

A situation where a chiral substrate is exposed to a chiral environment which can influence its reactivity.

Specific Rotation

The angle by which a chiral substance rotates plane-polarized light, expressed under standardized conditions.

Chirality in Nature

The phenomenon where many biological processes and molecules are chiral, affecting their function and interaction.