1. CHE-240 Unit 1 Structure and Stereochemistry of Alkanes CHAPTER TWO Terrence P. Sherlock Burlington County College 2004

2. Chapter 22 Multiple Bonds A double bond (2 pairs of shared electrons) consists of a sigma bond and a pi bond. A triple bond (3 pairs of shared electrons) consists of a sigma bond and two pi bonds. =>

3. Chapter 23 Molecular Shapes Bond angles cannot be explained with simple s and p orbitals. Use VSEPR theory. Hybridized orbitals are lower in energy because electron pairs are farther apart. Hybridization is LCAO within one atom, just prior to bonding. =>

4. Chapter 24 sp Hybrid Orbitals 2 VSEPR pairs Linear electron pair geometry 180° bond angle =>

5. Chapter 25 sp 2 Hybrid Orbitals 3 VSEPR pairs Trigonal planar e - pair geometry 120° bond angle =>

6. Chapter 26 sp 3 Hybrid Orbitals 4 VSEPR pairs Tetrahedral e - pair geometry 109.5° bond angle =>

7. Chapter 27 Sample Problems Predict the hybridization, geometry, and bond angle for each atom in the following molecules: Caution! You must start with a good Lewis structure! NH 2 CH 3 -C  C-CHO =>

8. Chapter 28 Bond Dipole Moments are due to differences in electronegativity. depend on the amount of charge and distance of separation. In debyes,  x  (electron charge) x d(angstroms) =>

9. Chapter 29 Molecular Dipole Moments Depend on bond polarity and bond angles. Vector sum of the bond dipole moments. Lone pairs of electrons contribute to the dipole moment. =>

10. Chapter 210 Intermolecular Forces Strength of attractions between molecules influence m.p., b.p., and solubility; esp. for solids and liquids. Classification depends on structure.  Dipole-dipole interactions  London dispersions  Hydrogen bonding =>

11. Chapter 211 Dipole-Dipole Forces Between polar molecules Positive end of one molecule aligns with negative end of another molecule. Lower energy than repulsions, so net force is attractive. Larger dipoles cause higher boiling points and higher heats of vaporization. =>

12. Chapter 212 Dipole-Dipole =>

13. Chapter 213 London Dispersions Between nonpolar molecules Temporary dipole-dipole interactions Larger atoms are more polarizable. Branching lowers b.p. because of decreased surface contact between molecules. =>

14. Chapter 214 Dispersions =>

15. Chapter 215 Hydrogen Bonding Strong dipole-dipole attraction Organic molecule must have N-H or O-H. The hydrogen from one molecule is strongly attracted to a lone pair of electrons on the other molecule. O-H more polar than N-H, so stronger hydrogen bonding =>

16. Chapter 216 H Bonds =>

17. Chapter 217 Boiling Points and Intermolecular Forces =>

18. Chapter 218 Solubility Like dissolves like Polar solutes dissolve in polar solvents. Nonpolar solutes dissolve in nonpolar solvents. Molecules with similar intermolecular forces will mix freely. =>

19. Chapter 219 Hydrocarbons Alkane: single bonds, sp 3 carbons Cycloalkane: carbons form a ring Alkene: double bond, sp 2 carbons Cycloalkene: double bond in ring Alkyne: triple bond, sp carbons Aromatic: contains a benzene ring =>

20. Chapter 220 Compounds Containing Oxygen Alcohol: R-OH Ether: R-O-R ' Aldehyde: RCHO Ketone: RCOR ' =>

21. Chapter 221 Carboxylic Acids and Their Derivatives Carboxylic Acid: RCOOH Acid Chloride: RCOCl Ester: RCOOR ' Amide: RCONH 2 =>

22. Chapter 222 Compounds Containing Nitrogen Amines: RNH 2, RNHR ', or R 3 N Amides: RCONH 2, RCONHR, RCONR 2 Nitrile: RCN =>

23. Chapter 223 POWER POINT IMAGES FROM “ORGANIC CHEMISTRY, 5 TH EDITION” L.G. WADE ALL MATERIALS USED WITH PERMISSION OF AUTHOR PRESENTATION ADAPTED FOR BURLINGTON COUNTY COLLEGE ORGANIC CHEMISTRY COURSE BY: ANNALICIA POEHLER STEFANIE LAYMAN CALY MARTIN