有机化学 第二讲.ppt

McMurry Organic Chemistry 6th edition Chapter 2 (c) 2003 2. Polar Covalent Bonds: Acids and Bases Why this chapter? Description of basic ways chemists account for chemical reactivity. Establish foundation for understanding specific reactions discussed in subsequent chapters. 2.1 Polar Covalent Bonds: Electronegativity Covalent bonds can have ionic character These are polar covalent bonds Bonding electrons attracted more strongly by one atom than by the other (HCl, HF) Electron distribution between atoms is not symmetrical (H2O) Bond Polarity and Electronegativity Electronegativity (EN): intrinsic ability of an atom to attract the shared electrons in a covalent bond Differences in EN produce bond polarity Arbitrary scale. As shown in Figure 2.2, electronegativities are based on an arbitrary scale F is most electronegative (EN = 4.0), Cs is least (EN = 0.7) Metals on left side of periodic table attract electrons weakly, lower EN Halogens and other reactive nonmetals on right side of periodic table attract electrons strongly, higher electronegativities EN of C = 2.5 The Periodic Table and Electronegativity Bond Polarity and Inductive Effect Nonpolar Covalent Bonds: atoms with similar EN Polar Covalent Bonds: Difference in EN of atoms 2 Ionic Bonds: Difference in EN 2 C–H bonds, relatively nonpolar C-O, C-X bonds (more electronegative elements) are polar Bonding electrons toward electronegative atom C acquires partial positive charge, ?+ Electronegative atom acquires partial negative charge, ?- Inductive effect: shifting of electrons in a bond in response to EN of nearby atoms Electrostatic Potential Maps Electrostatic potential maps show calculated charge distributions Colors indicate electron-rich (red) and electron-poor (blue) regions Arrows indicate direction of bond polarity 2.2 Polar Covalent Bonds: Dipole Moments Molecules as a whole are often polar from vector summation of individual bond polarities and lone-pair contributions Strongly polar substance