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5: Stereochemistry at Tetrahedral Centers

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    Learning Objectives

    After you have completed Chapter 5, you should be able to

    • fulfill all of the detailed objectives listed under each individual section.
    • use molecular models in solving problems on stereochemistry.
    • solve road-map problems that include stereochemical information.
    • define, and use in context, the new key terms.

    This chapter introduces the concept of chirality, and discusses the structure of compounds containing one or two chiral centers. A convenient method of representing the three-dimensional arrangement of the atoms in chiral compounds is explained; furthermore, throughout the chapter , considerable emphasis is placed on the use of molecular models to assist in the understanding of the phenomenon of chirality. The chapter continues with an examination of stereochemistry—the three-dimensional nature of molecules. The subject is introduced using the experimental observation that certain substances have the ability to rotate plane-polarized light. Finally, certain reactions of alkenes are re-examined in the light of the new material encountered in this chapter.

    • 5.0: Chapter Objectives and Introduction
    • 5.1: Enantiomers and the Tetrahedral Carbon
      Stereoisomers are isomers that differ in spatial arrangement of atoms, rather than order of atomic connectivity. One of the most interesting types of isomer is the mirror-image stereoisomer, a non-superimposable set of two molecules that are mirror images of one another. The existence of these molecules are determined by a a concept known as chirality.
    • 5.2: The Reason for Handedness in Molecules - Chirality
    • 5.3: Optical Activity
      Identifying and distinguishing enantiomers is inherently difficult, since their physical and chemical properties are largely identical. Fortunately, a nearly two hundred year old discovery by the French physicist Jean-Baptiste Biot has made this task much easier. This discovery disclosed that the right- and left-handed enantiomers of a chiral compound perturb plane-polarized light in opposite ways. This perturbation is unique to chiral molecules, and has been termed optical activity.
    • 5.4: Pasteur's Discovery of Enantiomers
      Because enantiomers have identical physical and chemical properties in achiral environments, separation of the stereoisomeric components of a racemic mixture or racemate is normally not possible by the conventional techniques of distillation and crystallization. In some cases, however, the crystal habits of solid enantiomers and racemates permit the chemist (acting as a chiral resolving agent) to discriminate enantiomeric components of a mixture
    • 5.5: Sequence Rules for Specifying Configuration
      The method of unambiguously assigning the handedness of molecules was originated by three chemists: R.S. Cahn, C. Ingold, and V. Prelog and, as such, is also often called the Cahn-Ingold-Prelog rules.
    • 5.6: Diastereomers
    • 5.7: Meso Compounds
      A meso compound is an achiral compound that has chiral centers. A meso compound contains an internal plane of symmetry which makes it superimposable on its mirror image and is optically inactive although it contains two or more stereocenters. Remember, an internal plane of symmetry was shown to make a molecule achiral.
    • 5.8: Racemic Mixtures and the Resolution of Enantiomers
      A racemic mixture is a 50:50 mixture of two enantiomers. Because they are mirror images, each enantiomer rotates plane-polarized light in an equal but opposite direction and is optically inactive. If the enantiomers are separated, the mixture is said to have been resolved. A common experiment in the laboratory component of introductory organic chemistry involves the resolution of a racemic mixture.
    • 5.9: A Review of Isomerism
    • 5.10: Chirality at Nitrogen, Phosphorus, and Sulfur
    • 5.11: Prochirality
      When a tetrahedral carbon can be converted to a chiral center by changing only one of its attached groups, it is referred to as a ‘prochiral' center.
    • 5.12: Chirality in Nature and Chiral Environments
    • 5.S: Stereochemistry at Tetrahedral Centers (Summary)
    • 5.xx: Enantiomers and Diastereomers

    Thumbnail: Two enantiomers of a generic amino acid that are chiral. (Public Domain; unknonw author via Wikipedia)

    5: Stereochemistry at Tetrahedral Centers is shared under a CC BY-SA 4.0 license and was authored, remixed, and/or curated by Dietmar Kennepohl.