Lecture 1 Reading

1.1

Atoms, Electrons, and Orbitals

Atomic number Z number of protons in nucleus

Wave function energy of electrons; found by Schrdinger (mathematical)
()
Heisenberg Uncertainty probability of finding an electron at point
Wave functions = orbitals, specifying size, shape, directional properties
S orbitals spherically symmetrical
Principal quantum number (n) specifies shell, relates energy of orbital,
period (row) corresponds to principal quantum number of highest occupied
orbital
Boundary surfaces volume where the probability of finding electron is high
(90-95%)
Spin quantum number + or -
Pauli exclusion principle two electrons may occupy same orbital only when
opposite spins
Nodal surfaces wave function changes sign, probability of finding electron
is 0
Hunds rule orbitals of equal energy
Valence electrons outermost electrons, most likely involved in chemical
bonding and reactions
1.2

Ionic Bonds

Chemical bond attractive force between atoms

Ionic bond force of attraction between oppositely charged ions, found in
inorganic chemistry
Cations positively charged ions
Anions negatively charged ions
Ionization energy large amount of energy, increases across a row in
periodic table
Endothermic absorbs energy (+)
Exothermic energy is released (-)
Electron affinity energy change for addition of an electron to an atom
Electrostatic (Coulombic) forces between oppositely charged particles
(constitute ionic bond)
Carbon known for sharing electrons rather than donating
1.3

Covalent Bonds, Lewis Formulas, and Octet Rule

Covalent (shared) electron pair sharing of two electrons by atoms

Bond dissociation enthalpy amount of energy required to dissociate
covalent bond
Main contributor to strength increased Coulombic force exerted on
electrons
Unshared pairs valence electrons not involved in covalent bond

Lecture 1 Reading
Lewis structures electrons represented by dots, shared pair bonds as lines,
limits second-row elements to 8 electrons
Octet rule achieve stable configuration by gaining, losing, or sharing
electrons
Carbon four valence electrons, forms four covalent bonds

1.4 Double Bonds and Triple Bonds

Shared electron pair bond four-electron = double bond, six-electron = triple
bond
1.5 Polar Covalent Bonds, Electronegativity, Bond Dipoles
Polar covalent electron distribution polarized (one atom has greater
tendency to attract electrons toward itself than the other)
Electronegativity tendency of atom to attract electrons in covalent bond
Electronegative element attracts electrons
Electropositive element donates electrons
Electrostatic potential map graphic representation to show charge
distribution using colors of rainbow (blue = positive to red = negative)
Paulings electronegativity values most commonly used electronegativity
scale
Electronegativity increases from left to right across row on PT and decreases
going down column
Most electronegative fluorine (F)
Least electronegative lithium (Li)
Greater electronegativity difference = more polar the bond
Bind dipole moment opposite charges are separated from each other
Dipole moment () product of amount of charge (e) multiplied by distance
(d) between centers of charge ( =e d )
Molecular dipole moments are on order of 10-18 esucm = 1 debye (D)
1.6 Formal Charges
Formal charge = Group number in PT Electron count
Electron count = (Number of shared electrons) + number of unshared
electrons
1.7 Structural Formulas of Organic Molecules
Molecular formula which atoms and how many of each are present
Connectivity partial structure shows order in which atoms are connected
Carbon 4 bonds
Nitrogen 3 bonds
Oxygen 2 bonds
Isomers different compounds same molecular formula
Constitutional (structural) isomer differ in connectivity

Lecture 1 Reading
Stereoisomers differ in arrangement of atoms in space
Covalent bonds revealed by connectivity information accounts for valence
electrons
Remaining valence electrons assigned as unshared pairs to complete Lewis
formulas
Consider molecule in which must include multiple bonds when writing Lewis
formula
Condensed formula omit bonds altogether, written in sequence, subscripts
indicate number of identical groups
Bond-line formulas (skeletal formulas) modified line formulas, labels for
carbon are omitted, hydrogens attached to carbon are shown only for clarity
when necessary; Heteroatoms atoms other than carbon or hydrogen,
shown explicitly as are hydrogens attached to them; unshared electron pairs
shown when necessary (often omitted)
1.8 Resonance
Resonance two or more Lewis formulas differ only in distribution of
electrons
True structure resonance hybrid of various Lewis formulas called
contributing structures
Double-headed arrow signify resonance
Resonance corrects fundamental defect in Lewis formulas
Localized how electrons are represented in Lewis formulas, either shared or
unshared
Delocalized shared by several nuclei
Average of Lewis formulas sometimes drawn using dashed line to represent
partial bond, of unit negative charge to each atom attached to partial
bond
Curved arrows keep track of delocalized electrons, convert one formula into
another by moving electron pairs, show origin and destination of a pair of
electrons
Various resonance structures not equivalent and do not contribute equally
to resonance hybrid
Important to understand factors that make one resonance form more
important (more stable) than another
Refer to Table 1.6
1.9 Sulfur and Phosphorus-Containing Organic Compounds and the Octet
Rule
Third-row elements vacant 3d orbitals permit accommodation of more than
8 electrons in valence shells
Sulfur-containing and phosphorus-containing compounds preferred doublebonded structure
Sulfur = 10-12 in valence
Phosphorus = 10 in valence
Only valence orbitals available to second-row elements are 2s and 2p, octet
rule cannot be exceeded

Lecture 1 Reading

1.10 The Shapes of Some Simple Molecules

Methane tetrahedral molecule, four hydrogens occupy corners of
tetrahedron with carbon at center
Three-dimensionality uses different bond styles solid wedge = bond that
projects into paper, hashed wedge = bond that projects into paper, simple
line = bond that lies in plane of paper
VSEPR (valence shell electron-pair repulsion) model electron pair (bonded
or unshared) will be as far away from atoms other electron pairs as possible
Tetrahedral angle = 109.5 (CH4)
Bent = 105 (H2O)
Trigonal pyramidal = 107 (NH3)
Trigonal planar = 120 (BF3)
Bonded pair-bonded pair (least repulsive) < Unshared pair-bonded pair <
Unshared pair-unshared pair (most repulsive)
Multiple bonds treated as single unit in VSEPR model

1.11 Molecular Dipole Moments

Molecular dipole moment resultant of all individual bond dipole moments of
a substance
Some molecules have polar bonds, lack dipole moment due to geometry
causing dipoles to cancel