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4th Edition
Paula Yurkanis Bruice
Chapter 1
Electronic Structure
and
Bonding
Acids and Bases
Irene Lee
Case Western Reserve University
Cleveland, OH
2004, Prentice Hall
Organic Chemistry
Organic compounds are compounds containing carbon
Carbon neither readily gives up nor readily accepts
electrons
Table 1.1
Covalent Compounds
Equal sharing of electrons: nonpolar covalent bond
(e.g., H2)
Sharing of electrons between atoms of different
electronegativities: polar covalent bond (e.g., HF)
A Dipole
A polar bond has a negative end and a positive end
dipole moment (D) = m = e x d
(e) : magnitude of the charge on the atom
(d) : distance between the two charges
Lewis Structure
Formal charge =
number of valence electrons
(number of lone pair electrons +1/2 number of bonding electrons)
two bonds
three bonds
four bonds
Cl
Br
The s Orbitals
The p Orbitals
Molecular Orbitals
An sp-Hybridized Carbon
Bonding in Water
Summary
A p bond is weaker than a s bond
The greater the electron density in the region of orbital
overlap, the stronger is the bond
The more s character, the shorter and stronger is the
bond
The more s character, the larger is the bond angle
An Acid/Base Equilibrium
H2O + HA
H3O+ + A-
[H3O+][A-]
Ka =
[H2O][HA]
pKa = -log Ka
Ka: The acid dissociation constant
pK a
HA
pH log
CH3COH
CH3CH2OH
pKa = 4.76
acetic acid
pKa = 15.9
ethanol
O
CH3CO-
O
CH3CO-