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CHE-240 Unit 1 Structure and Stereochemistry of Alkanes CHAPTER TWO

CHE-240 Unit 1 Structure and Stereochemistry of Alkanes CHAPTER TWO. Terrence P. Sherlock Burlington County College 2004. =>. Multiple Bonds. A double bond (2 pairs of shared electrons) consists of a sigma bond and a pi bond.

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CHE-240 Unit 1 Structure and Stereochemistry of Alkanes CHAPTER TWO

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

  2. => 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. Chapter 2

  3. 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. => Chapter 2

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

  5. => sp2 Hybrid Orbitals • 3 VSEPR pairs • Trigonal planar e- pair geometry • 120° bond angle Chapter 2

  6. => sp3 Hybrid Orbitals • 4 VSEPR pairs • Tetrahedral e- pair geometry • 109.5° bond angle Chapter 2

  7. => 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! • NH2NH2 • CH3-CC-CHO Chapter 2

  8. are due to differences in electronegativity. depend on the amount of charge and distance of separation. In debyes,  = 4.8 x (electron charge) x d(angstroms) => Bond Dipole Moments Chapter 2

  9. => 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. Chapter 2

  10. 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 => Chapter 2

  11. 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. => Chapter 2

  12. Dipole-Dipole => Chapter 2

  13. => 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. Chapter 2

  14. Dispersions => Chapter 2

  15. 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 => Chapter 2

  16. H Bonds => Chapter 2

  17. => Boiling Points and Intermolecular Forces Chapter 2

  18. Solubility • Like dissolves like • Polar solutes dissolve in polar solvents. • Nonpolar solutes dissolve in nonpolar solvents. • Molecules with similar intermolecular forces will mix freely. => Chapter 2

  19. Hydrocarbons • Alkane: single bonds, sp3 carbons • Cycloalkane: carbons form a ring • Alkene: double bond, sp2 carbons • Cycloalkene: double bond in ring • Alkyne: triple bond, sp carbons • Aromatic: contains a benzene ring => Chapter 2

  20. => Compounds Containing Oxygen • Alcohol: R-OH • Ether: R-O-R' • Aldehyde: RCHO • Ketone: RCOR' Chapter 2

  21. => Carboxylic Acids and Their Derivatives • Carboxylic Acid: RCOOH • Acid Chloride: RCOCl • Ester: RCOOR' • Amide: RCONH2 Chapter 2

  22. => Compounds Containing Nitrogen • Amines: RNH2, RNHR', or R3N • Amides: RCONH2, RCONHR, RCONR2 • Nitrile: RCN Chapter 2

  23. POWER POINT IMAGES FROM “ORGANIC CHEMISTRY, 5TH EDITION”L.G. WADEALL MATERIALS USED WITH PERMISSION OF AUTHORPRESENTATION ADAPTED FOR BURLINGTON COUNTY COLLEGEORGANIC CHEMISTRY COURSEBY:ANNALICIA POEHLER STEFANIE LAYMAN CALY MARTIN Chapter 2

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