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6: Bonding in Organic Molecules

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  • In previous chapters, we have shown how you can use ball-and-stick models to predict the general arrangements in space of organic molecules. The sticks correspond to chemical bonds, which we represent in structural formulas as lines, or in Lewis structures as pairs of dots denoting shared pairs of electrons. Remembering that electrons and nuclei are charged particles, and that it is electrical forces of attraction and repulsion between the electrons and nuclei that determine the bonding, perhaps we should be surprised that such simple mechanical models provide so much useful information. What we will try to do in this chapter is to show you how the modern electronic theory of chemical bonding provides strong support for the use of ball-and-stick models for many organic molecules, and also where it indicates that the models need to be modified or cannot properly represent the structural arrangements.

    • 6.1: Prelude to Bonding
      here are several qualitative approaches to bonding in polyatomic molecules, but we shall discuss here the most widely used and currently popular approach. This approach involves setting up appropriate atomic orbitals for the atoms and considering that each bond arises from the attractive electrical forces of two or more nuclei for a pair of electrons in overlapping atomic orbitals, with each orbital on a different atom.
    • 6.2: Hydrogenlike Atomic Orbitals
      With the modern concept of a hydrogen atom we do not visualize the orbital electron traversing a simple planetary orbit. Rather, we speak of an atomic orbital, in which there is only a probability of finding the electron in a particular volume a given distance and direction from the nucleus. The boundaries of such an orbital are not distinct because there always remains a finite, even if small, probability of finding the electron relatively far from the nucleus.
    • 6.3: Bond Formation Using Atomic Orbitals
      In writing the conventional Lewis structures for molecules, we assume that a covalent chemical bond between two atoms involves sharing a pair of elections, one from each atom. Figure 6-5 shows how atomic orbitals can be considered to be used in bond formation. Here, we postulate that a single bond is formed by the pulling together of two atomic nuclei by attractive forces exerted by the nuclei for the two paired electrons in overlapping atomic orbitals.
    • 6.4: Electron Repulsion and Bond Angles. Orbital Hybridization
      Page notifications Off Save as PDF Share In predicting bond angles in small molecules, we find we can do a great deal with the simple idea that unlike charges produce attractive forces while like charges produce repulsive forces. We will have electron-nuclear attractions, electron-electron repulsions, and nucleus-nucleus repulsions.
    • 6.5: Atomic-Orbital Models
      The construction of several atomic orbital models for differing classes of organic molecules is presented.
    • 6.6: Resonance
      Bonding electrons can be associated with more than two nuclei, and there is a measure of stability to be gained by this because the degree of bonding increases when the electrons can distribute themselves over a greater volume. This effect often is called electron delocalization or resonance. It is important only if the component atomic orbitals overlap significantly, and this will depend in large part on the molecular geometry.
    • 6.7: Advanced Quantum Theory of Organic Molecules
      In recent years, great progress has been made in quantum-mechanical calculations of the properties of small organic molecules by so-called ab initio methods, which means calculations from basic physical theory using only fundamental constants, without calibration from known molecular constants. Calculations that are calibrated by one or more known properties and then used to compute other properties are called "semiempirical" calculations.
    • 6.E: Bonding in Organic Molecules (Exercises)
      These are the homework exercises to accompany Chapter 6 of the Textmap for Basic Principles of Organic Chemistry (Roberts and Caserio).

    Contributors and Attributions

    John D. Robert and Marjorie C. Caserio (1977) Basic Principles of Organic Chemistry, second edition. W. A. Benjamin, Inc. , Menlo Park, CA. ISBN 0-8053-8329-8. This content is copyrighted under the following conditions, "You are granted permission for individual, educational, research and non-commercial reproduction, distribution, display and performance of this work in any format."

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