Chapter 1 Introduction and

Review
CHM 2210 Organic Chemistry I
Broward community College Central Campus
Assistant Professor Joseph Lawry, Instructor
2003 All rights reserved. Use of this material for any
purpose other than education without expressed consent
is prohibited.

Graphic Representation of a 1s
orbital
Electrons bound to a
nucleus are found in
orbitals. Heisenberg
Uncertainty principle
disallows simultaneous energy and
position determination
but we can find
probability or e- density
from

2s orbital is spherically
symmetrical, has a node
Because most of the
electron density is in the
second concentric shell
past the node, the 2s
orbital is said to be
higher in energy than the
1s orbital. Again, this edensity map is obtained
by the square of the
eigenfunction,

2p orbitals consist of 3 degenerate subshells,

bi-lobed and orthagonal to each other.

Review list of Quantum terms

Orbital, shell, subshell

Heisenberg Uncertainty Principle
Node, nodal plane
Degenerate orbital
Aufbau and Pauli Exclusion Principles
Hunds Rule
Valence electrons

Electronic Configurations tell us that

the valence electrons are given by the
group number

Carbon hybridizes one s and three p

orbitals to form four sp3 molecular
orbitals
Saturated or singly
bonded carbon directs
four bonded atoms to the
corners of a regular
tetrahedron, shown by
methane, the simplest of
the hydrocarbon family
known as alkanes. When
pure carbon bonds to
itself in this manner, a
diamond results.

Nonbonding e-s are called lone

pairs

Lone pairs are often involved in reactions. For

example the lone pairs of ethanol can be
protonated under acidic conditions, setting up H2O
to leave the molecule to form an alkene or ether.

Carbon can single (sp3), double

(sp2) or triple (sp) bond to itself or
other heteroatoms (Prob.s 1-1, 1-2& 1-3)

Organic Chemistry Hinges on the

covalent bonding properties of C,
N, O, H, X [halogens], S and P

Carbon generally binds four times with no unshared or nonbonding electrons. Nitrogen forms 3 bonds with 1 pair of nonbonding electrons, oxygen 2 bonds with 2 unshared pairs and
the halogens 1 time with 3 unshared pairs. Carbons ability to
form single, double and triple bonds to heteroatoms, like
oxygen, nitrogen, and halogens imparts polarity and
sythetically reactive functional groups.

Electronegativity refers to the the affinity

for electrons of an atom in a covalent bond;
differing E.N.s in a molecule lead to a
polar covalent bond

Students must familiarize themselves with the

Common Bonding Patterns. Formal Charge, (FC)
=[group #] [nonbonding e-s] [shared e-s]

Resonance Hybrids can show important

delocalization of charge

REVIEW RULES (pp.15-16) 1. valid Lewis structures

2. only e-s may be shifted (double bonds & lone pairs)
3. Unpaired e-s must remain the same. 4. Major
contributor is lowest energy 5. *Resonance is most
important when it serves to delocalize a charge over two
or more atoms. (this is the answer to many exam Q.s)

Acetate, the anion to acetic acid is

resonance stabilized

The two resonance structures of acetate show a

delocalization of charge between the two oxygens;
neither oxygen which is electro- negative an likes
electrons anyway, feels the full negative charge. This
delocalization is said to be a net stabilizing effect.

Resonance forms are not equal in

contribution.
As shown below with the resonance forms of
formaldehyde, the more stable form is the major
contributor and the less stable form the minor
contributor. Evaluation of the stability of resoncne
form is a critical skill in the study of Organic Chem.

Condensed structural formulas

are a type of structural shorthand

Condensed structural formulas for

double (sp2) and triple bonded (sp)
compounds

Line-angle, line-bond, skeletal

structure or stick figure
formulas are most common
representations of carbon cpd.s

Molecular Formulas and

Empirical Formulas
Elemental analysis gives us the % of C, H and O
of a compound of unknown formula. Assuming
100g of the unknown, we can calculate the moles
of each, divide each of these numbers of moles
by the smallest one to give molar ratios for the
empirical formula. Mass spectrometry will give
us the molecular weight. The correct formula
can be deduced as shown on pp.20-21; Students should
familiarize themselves with problem 1-12 pp. 21

Arrhenius acids and bases

According to Arrhenius, acids dissociate in water to give

H3O+ and A- (where A = acid anion). Strong acids
dissociate ~100%, while weak acids ionize ca. 5%/95%.
All carboxylic acids are weak acids, the lower the pKa
the stronger the acid. Arrhenius bases give OH-

Arrhenius Bases dissociate in H2O to give

hydroxide ion, OH-; Ion Product Equation
can give us acidity or basicity.
Strong bases such as NaOH dissociate more completely
than weaker, sparingly soluble bases such as Mg(OH)2.
The acidity or basicity of a solution can be measured by
solving the equation: Kw = [H3O+][-OH] = 1.00 x 10-14
24oC

Bronstead-Lowry acids are proton donors,

Bronstead-Lowry bases, proton
acceptors;B-L acids and bases ionize to
form conjugate pairs.

The Strength of a Bronstead-Lowry

acid is the extent it ionizes in H2O

HA + H2O H3O+ + AKa = [H3O+][A-] / [HA] ; For water,

the Ka and the pKa can be calculated by
knowing [H3O+][OH-] = 1.00 x 10-14 and
[H2O]= 55.6 mol / L*, so
Ka = [H3O+][OH-]/[H2O]= 1.00 x 10-14 /55.6
= 1.8 x 10-16 and log1.8 x 10-16 = -15.7 so
then, the pKa of water is 15.7 *= 1000g/L / 18g/mol

Acid Strength is related to the

pKa : the lower the pKa, the stronger the acid.
The higher the pKa, the stronger the base.

Structural Effects on Acidity and Basicity: the

more stable the conjugate base, the stronger
the acid (For exam: problems 1-14, 1-15, 1-16, 1-17, 1-18 & 1-19)

Acid strength is determined by

conjugate base stability

Previously, lower charge density stabilized the

conj. base, thus made stronger the acid. Here
are two cases where delocalization of a negative
charge stabilizes the conjugate base, thus
resulting in a stronger acid (eg.lower pKa )

Nucleophiles are Lewis bases with

a pair of electrons to donate to a
Lewis acid electrophile.curved arrows