CHEM 12
FOOTHILL COLLEGE
WADE CHAPTERS ONE & TWO OUTLINE
STRUCTURE, BONDING AND ACID-BASE IN ORGANIC CHEMISTRY
1) Introduction to Organic Chemistry
2) Communicating about Organic Chemistry: Structures and Nomenclature
a) Lewis Structures Section1-4
i) Octet vs non-octet structures
ii) Connecting the atoms correctly: Molecular Formula vs Structural Formula
iii) Common elements in Organic Chemistry: C, H, N, O, S, X
iv) Algorithm to predict presence or absence of multiple bonds in an octet
structure:
# bonds =( need – have )÷2
need = e- needed for individual atoms to have filled shell
have = valence electrons for each individual atom± charge
b) Formal charge Section1-7
F.C. on atom = (number of e– assigned to atom in structure) – # valence
electrons of atom
(number of e– assigned to atom in structure )= both from lone pair; just one
from covalent bond
c) Resonance Section1-9
i) Moving pi electrons in octet structures
ii) Relative importance of alternative resonance forms
(1) All octet (CH2O)
(2) Charge on atoms w complimentary electronegativity (NCO–)
(3) Minimum charge (CHCOOH)
(4) Maximum # bonds (H2SO4)
d) Acid-Base Chemistry
i) Bronsted vs Lewis Acids
ii) The Ka and the pKa
iii) Predicting the position of equilibrium when water is not the base
iv) Stability of Ion typically dictates position of equilibrium
v) Factors that influence anion stability
(1) Atom bearing charge
(a) Electronegativity (across row/ period)
(b) Size (down column /group)
(2) Resonance delocalization stabilizes charge
(3) Hybridization state: more s-character stabilizes anion
(4) Inductive effect: through-bond e– withdrawl induces dipoles which
stabilizes anion
Chapter Two
3) Atomic Orbitals: definition
4) Hybridization of Atomic Orbitals
Section 2-6
5) Molecular Orbitals
Section 2-2
6) Sigma vs pi
Section 2-3
7) Structural Isomers vs Conformers: Bond Rotation Section 2-7
8) The Molecular Orbital Energy Diagram
a) H2
Section 2-3
b) CH4 Notes only
CHEM 12
FOOTHILL COLLEGE
WADE CHAPTERS ONE & TWO OUTLINE
STRUCTURE, BONDING AND ACID-BASE IN ORGANIC CHEMISTRY
c) CH2CH2
Notes only
9) Bond Polarity and its influence on Intermolecular Forces
a) Ion-Ion
b) Ion-Dipole
c) H-Bonding
d) Dipole-Dipole
e) Dipole- Induced Dipole
f) Induced Dipole-Induced Dipole (Van der Waals)
10)Functional Groups in Organic Chemistry
Memorization List: Inside cover of Text
11)Drawing Organic Compounds
i) Bond-Line Formulas with and without 3D
ii) Hydrocarbon definition and the alkyl group R
LEARNING OUTCOMES:
 Gain Appreciation for relevance of Organic Chemistry to everyday experience
 Draw Organic Molecules using modified Lewis Structures
 Understand electron distribution in molecules with the concept of Resonance
 Visualize shapes of simple Organic Molecules
 Predict Hybridization States
 Describe Bonding according to Molecular Orbital Theory
 Understand relationship between stability of product in equilibrium and
equilibrium constant
 Predict acidity trends for bronsted acids based on conjugate base stability
 Understand the structural features which most commonly influence the position
of an acid-base equilibrium.
 Calculate concentrations of molecular species on either side of chemical
equilibrium equations from thermodynamic functions G and Keq.
 Rank acidity of common functional groups.
SAMPLE PROBLEMS:
1)
A) Complete the following Lewis Structure of neutral CH2N2 including any
multiple bonds, non-bonded electrons and formal charges.
B) Draw a second valid resonance form. Include non-bonded electrons and
formal charges.
C) Label each resonance form as a MAJOR, MINOR, or EQUAL contributor to the
overall structure.
CHEM 12
FOOTHILL COLLEGE
WADE CHAPTERS ONE & TWO OUTLINE
STRUCTURE, BONDING AND ACID-BASE IN ORGANIC CHEMISTRY
2) Consider the Molecular Orbital Energy Diagram for acetylene C2H2 below:
E
To H
To H
A) Identify the hybridized atomic orbitals in the diagram. Label their positions
on the diagram.
B) Label each Molecular Orbital whose energy is depicted in the diagram as a ,
*,  or * orbital.
C) Tell whether the C2H2+ or C2H2– is more stable. Explain.
D) Label the LUMO(s) in the diagram.
3) Which of the following best describes the bonding for the indicated bond in the
structure below?
A)
B)
C)
D)
E)
Csp3 + Osp2
Csp3 + Osp
Csp2 + O sp3
C sp2 + Osp
Csp2 + Op
4)
Indicate whether each of the equilibria below are favored to the right, to the
left or neither by circling the symbol which best characterizes the value of the
equilibrium constant Keq. Explain each answer briefly:
CHEM 12
FOOTHILL COLLEGE
WADE CHAPTERS ONE & TWO OUTLINE
STRUCTURE, BONDING AND ACID-BASE IN ORGANIC CHEMISTRY
a.
b.
CHAP ONE OUTLINE: WADE
IMPORTANT CONCEPTS FROM GENERAL CHEM