WHAT IS ORGANIC CHEMISTRY

REVIEW OF MOLECULAR STRUCTURE

I. Schematic View of the Atom
a. REVIEW Gen Chem Principles
b. Makeup of the atom

i. Nucleus
ii. Electrons

c. Electron Configurations of the Atoms

i. Energy levels, i.e. Shells (s, p, d. f)

ii. Rules for adding electrons to shells

1.Aufbau principle - orbitals fill in order
of increasing energy from lowest energy
to highest energy
2.Pauli exclusion principle- only two
electrons can occupy an orbital and their
spins must be paired
3.Hunds Rule - when orbitals of equal
energy are available but there are not
enough electrons to fill all of them, one
electron is added to each orbital before a
second electron is added to any one of
them

iii. Paired electrons

iv. Ground state electron configurations of

atoms (Table 1.1)

v. Electron configurations of ions and

complete valence shells

II. Lewis Structures

a. Lewis representation

i. Valence shell

ii. Valence Electrons

iii. Lewis depiction of atoms and ions

b. Lewis Model of Bonding

i. Ionic bonds

1.Attraction between cation and anion

ii. Covalent bonds

1. Sharing of valence electrons between

atoms

iii. Polar covalent bonds

1.Covalent bonds with non-equal sharing

of electrons

c. Features of Covalent Bonds

i. Single electron from each atom forms an
electron pair
ii. Electron pair is shared by two atoms, and
fills each atoms valence shell
iii. Multiple pairs can be shared

d.Drawing Lewis Structures

i. determine the number of valence electrons

ii. determine the arrangement of atoms

iii. connect the atoms by single bonds

iv. arrange the remaining electrons so that each

atom has a complete valence shell

v. show a bonding pair of electrons as a single

line

vi. show a nonbonding pair of electrons as a

pair of dots

e. Stable bonding in neutral molecules

i. Multiple bonding

III. Polar Covalent Bonds

a. Electronegativity

b. How polar is the bond?

i. Partial charge notation

ii. Dipole size and Typical bond polarities

c. Polarity of molecules

d. Polarity and electrostatic maps

e. Formation of ions

f. Formal charge in atoms in molecules

Formal
charge

Number of
= valence electrons
in th e neutral,
un bonded atom

All
One h alf of
un shared + all sh ared
electrons
electrons

g. Exceptions to the octet rule

IV. Resonance
a. A single structure does not always accurate
depict the bonding in the molecule
b.The molecule is a hybrid of contributing
resonance structures

c. Requirements for assessing resonance structures

(VERY IMPORTANT to know). All structures
must
i. have the same number of valence electrons
ii. obey the rules of covalent bonding
1.no more than 2 electrons in the valence
shell of H
2.no more than 8 electrons in the valence
shell of a 2nd period element
3.3rd period elements, such as P and S,
may have up to 12 electrons in their
valence shells
iii. differ only in distribution of valence
electrons; the position of all nuclei must
be the same
iv. have the same number of paired and
unpaired electrons

d.Interconverting structures by using curved

arrow notation

i. Move a bonding pair of electrons onto an

atom to form a lone pair

ii. Move a lone pair from an atom between two

atoms to form a bond

iii. Watch formal charges being created and

destroyed along the way!

e. Assessing quality of resonance structures

i. All resonance structures CAN contribute,

but some contribute more or less.

ii. Need to be able to recognize between

contributing and non-contributing structures,
and how much each contributing structure
contributes

iii. We will try to emphasize important

contributing resonance structures. Pay
attention when we do!

V. Representing organic molecules

a. Structures are subsets of molecular formulas

b.Condensed structural formulas

i. Based on carbon having 4 bonds, oxygen
makes two, nitrogen makes 3, hydrogen
makes 1
ii. Show groups connected to each carbon

iii. Add heteroatoms

c. Line/angle structures
i. Carbons are not shown but are indicated as
1.Intersections
2.Vertices

ii. Show heteroatoms explicitly with hydrogens

d.Combined structures
i. If you show C, MUST show what is
connected to it (all valence)

ii. Trivalent C must have charges assigned (or

radicals more on that later)

VI. Acids and Bases review pKa material from Gen

Chem 2

a. Definitions
i. Ahrrenius acids and bases

ii. Bronsted-Lowry acids and bases

1.Acid-base reactions

2.Conjugate acid-base pairs

3.Using curved arrow notation in acidbase reactions

4.Determining site of protonation in

organic molecules

5.Using Ka to measure strengths of acids

6.Determining equilibrium constants of

proton transfer reactions by using
pKas

a.Determine the side favored at

equilibrium

b.Calculate pK

iii. Lewis acids and bases

iv. Almost all molecules can act as either acids

or bases (or both)
1.The question is not whether something is
an acid or a base, but HOW acidic is it,
and HOW basic is it.