2. Chapter 1 Introduction and Review Organic Chemistry, 5 th Edition L. G. Wade, Jr. Jo Blackburn Richland College, Dallas, TX Dallas County Community College District  2003,  Prentice Hall

3. Chapter 12 Definitions Old: “derived from living organisms” New: “chemistry of carbon compounds” From inorganic to organic, Wöhler, 1828 =>

4. Chapter 13 Atomic Structure protons, neutrons, and electrons isotopes =>

5. Chapter 14 Atomic Orbitals 2s orbital (spherical) 2p orbital =>

6. Chapter 15 Electronic Configurations Aufbau principle: Place electrons in lowest energy orbital first. Hund’s rule: Equal energy orbitals are half- filled, then filled.   => 

7. Chapter 16 Table 1-1 =>

8. Chapter 17 Bond Formation Ionic bonding: electrons are transferred. Covalent bonding: electron pair is shared. =>

9. Chapter 18 Lewis Structures Bonding electrons Nonbonding electrons or lone pairs Satisfy the octet rule! =>

10. Chapter 19 Multiple Bonding =>

11. Chapter 110 Dipole Moment Amount of electrical charge x bond length. Charge separation shown by electrostatic potential map (EPM). Red indicates a partially negative region and blue indicates a partially positive region. =>

12. Chapter 111 Electronegativity and Bond Polarity Greater  EN means greater polarity =>

13. Chapter 112 Calculating Formal Charge For each atom in a valid Lewis structure: Count the number of valence electrons Subtract all its nonbonding electrons Subtract half of its bonding electrons =>

14. Chapter 113 Ionic Structures X =>

15. Chapter 114 Resonance Only electrons can be moved (usually lone pairs or pi electrons). Nuclei positions and bond angles remain the same. The number of unpaired electrons remains the same. Resonance causes a delocalization of electrical charge. Example 

16. Chapter 115 Resonance Example The real structure is a resonance hybrid. All the bond lengths are the same. Each oxygen has a -1/3 electrical charge. =>

17. Chapter 116 Major Resonance Form has as many octets as possible. has as many bonds as possible. has the negative charge on the most electronegative atom. has as little charge separation as possible. Example 

18. Chapter 117 Major Contributor? majorminor, carbon does not have octet. =>

19. Chapter 118 Chemical Formulas Full structural formula (no lone pairs shown) Line-angle formula Condensed structural formula Molecular formula Empirical formula CH 3 COOH C 2 H 4 O 2 CH 2 O =>

20. Chapter 119 Calculating Empirical Formulas Given % composition for each element, assume 100 grams. Convert the grams of each element to moles. Divide by the smallest moles to get ratio. Molecular formula may be a multiple of the empirical formula. =>

21. Chapter 120 Arrhenius Acids and Bases Acids dissociate in water to give H 3 O + ions. Bases dissociate in water to give OH - ions. K w = [H 3 O + ][OH - ] = 1.0 x 10 -14 at 24°C pH = -log [H 3 O + ] Strong acids and bases are 100% dissociated. =>

22. Chapter 121 Br Ø nsted-Lowry Acids and Bases Acids can donate a proton. Bases can accept a proton. Conjugate acid-base pairs. => acid base conjugate base conjugate acid

23. Chapter 122 Acid and Base Strength Acid dissociation constant, K a Base dissociation constant, K b For conjugate pairs, (K a )(K b ) = K w Spontaneous acid-base reactions proceed from stronger to weaker. pK a 4.74pK b 3.36pK b 9.26pK a 10.64 =>

24. Chapter 123 Determining Relative Acidity Electronegativity Size Resonance stabilization of conjugate base =>

25. Chapter 124 Electronegativity As the bond to H becomes more polarized, H becomes more positive and the bond is easier to break. =>

26. Chapter 125 Size As size increases, the H is more loosely held and the bond is easier to break. A larger size also stabilizes the anion. =>

27. Chapter 126 Resonance Delocalization of the negative charge on the conjugate base will stabilize the anion, so the substance is a stronger acid. More resonance structures usually mean greater stabilization. =>

28. Chapter 127 Lewis Acids and Bases Acids accept electron pairs = electrophile Bases donate electron pairs = nucleophile nucleophileelectrophile =>

29. Chapter 128 End of Chapter 1