University Of Pennsylvania

College of General Studies

Professor William A. Price, Ph.D.

CHEM 241-601
Organic Chemistry, 9th Edition
By T.W. Graham Solomons

From the Bark of the

Pacific Yew Tree
O

NH

OH

O
O

OH

OH O O
O

Taxus brevifolia

Introduction:
Structure and Bonding
Atomic structure
Lewis Structures
Resonance
Structural Formulas
Acids and Bases

Nucleus is a Tiny Fraction of

the Volume of an Atom

Orbitals are Probabilities

2s Orbital Has a Node

The p Orbital

px, py, pz

Electron Configurations

Lewis Dot Structure of

Methane
carbon - 4 valence e

.
.C.
.

1s22s22p2

hydrogen - 1 valence e

H.
1s

Tetrahderal Geometry

Bonding Characteristics of
Period 2 Elements

Saturated with Hydrogen

All Have the Same Geometry

All Have 4 Regions of Electron Density

A Saturated Hydrocarbon

Nitromethane

Nitromethane has 2 Formal

Charges

Formal Charge = [Group #] - [# bonds] - [# non-bonding electron

H
CH3NO2

H
H

O
C

N = 5-4-0 = +1

O = 6-1-6 = -1

N
O

Both Resonance Structures

Contribute to the Actual Structure
CH3NO2
H
H
H

O
C

H
H C

N
O

O
N

2 Equivalent Resonance Structures

Resonance Rules
Cannot break single (sigma) bonds
Only electrons move, not atoms
3 possibilities:
Lone pair of e- to adjacent bond position
Forms bond

bond to adjacent atom

bond to adjacent bond position

Curved Arrow Formalism

Shows flow of electrons

H
H
H

H C
H

O
N

Arrows depict electron pairs moving

Resonance Stabilization of Ions

Pos. charge is delocalized
H

H
C

C
C

H
C

C
C
H

H
H
C C
H
C
H
H
resonance hybrid

Bonding Pattens for C, N, and O

sp3
tetrahedral geometry

sp
linear

sp2
trigonal planar

C
C

Common Cationic, Neutral and

Anionic Forms

Two Nonequivalent Resonance

Structures in Formaldehyde

Resonance in Acetate Anion

Resonance in [CH2NH2]+

Propose Lewis Structures

a) H2CO2 b) O3

c) N2O

d) NH3O e) C2H3ClO

f) C2H5NO

Problem
Draw [NO2]+ and [NO2]-. Which ion has a
localized charge and which has a
delocalized charge. Explain.

Drawing Structures
H
H

C
H

H
C
H

H
C
H

H
C
H

Butane, C4H10
CH3CH2CH2CH3

H C C C
H
H
H
C
H
H
H
Methylpropane, C 4H10
CH3CH(CH3)CH3

Octane Representations
C8H18 is molecular formula but there are 18 possible structural isomers
H

H H H H H H
H
C
C
C
C
H
C
C
C
C
H
H H H HH H
HH
Lewis structure

CH3CH2CH2CH2CH2CH2CH2CH3
CH3(CH2)6CH3
condensed structural formula

Condensed
Formulas

Line-Angle Structures are

Often Used as a Short-hand
H

H H H H H H
H
C
C
C
C
H
C
C
C
C
H
H H H HH H
HH
Lewis structure

Line-angle or "zig-zag" structures

Line-Angle Structures
C12H26

H
H

H
H
H

C
H H

H
H

H
H

C
C

H
H

C
H

C
H

C
H
H

H
H

H H

H
H
H

H
H

H
H

At the end of every line and at the intersection of any lines

there is a carbon atom with 4 bonds. Hydrogen atoms
are mentally supplied to fill the valency to 4.
H
H

H
H

H
H
H

H H

H
H
H

H
H

H
H

Line-Angle structure
Superimposed on Lewis Structure
H
H

H
H
H

C
H H

H
H

H
H

C
H

C
C

C
H

C
H

C
H
H

H
H

Double Bonds are Shown

Depictions of trans 2-pentene
H
H
H

C
C
H

C H
H

H H
Lewis Structure

CH3

H
C

CH2CH3

condensed structural formula

line-angle or zig-zag structure

For Cyclic Structures, Draw the

Corresponding Polygon
Cyclohexane
H H
H
H
C
C H
H C
H C
C H
C
H
H
H
H

Some Steroids
OH

HO
Cholesterol
C27H44O

Testosterone
C19H26O2

Adrogenic/Anabolic Steroids
CH3 OH
CH3

CH3 O

H
O

CH3
H

H
H

O
Testosterone

Androstenedione

Anabolic Steroids
CH3 OH
CH3

CH3 OH
H
H

CH3
H

H N

H
N

O
Nandralone

Stanozolol

H
H

Benzene can be drawn as one of

two resonance structures
H
H
H

C
C

C
C
H

H
C
C

H
H

H
H

C
C

C
C
H

C
C

H
H

Some Line-Angle Structures