Structure Forms Empirical Formula

C 3H 8 H 3C CH 2 CH 3 H H
H H

CH3CH2CH3 H H H H
condensed Wedge/dash
skeletal
 Formulas and Structures
H O
• Full structural formula H C C O H
(expanded structural
formula) H
O
• Line-angle formula
(Skeletal structural formula) OH

• Condensed structural CH3COOH

formula
C2H4O2
• Molecular/Chemical
formula

• Empirical formula CH2O

 Several ways of writing organic
structures .

• Example – Butane: C4H10

CH3CH2CH2CH3 CH3-CH2-CH2-CH3

H H H H

H–C–C–C–C–H

H H H H
 Structural formulas of organic compounds

structural formula condensed formula line-angle formula

H H H H H
H C C C C C H CH3CH2CH2CH2CH3
H H H H H

H H OH H CH3CH2CHCH3
H C C C C H OH
OH
H H H H CH3CH2CH(OH)CH3
O
H O H
CH3CCH3 O
H C C C H
CH3COCH3
H H
(CH3)2CO
• The three-carbon alkane CH3CH2CH3, called propane,
has a molecular formula C3H8. Note in the 3-D drawing
that each C atom has two bonds in the plane (solid
lines), one bond in front (on a wedge) and one bond
behind the plane (on a dashed line).
Three-dimensional structure of some
cycloalkanes
 Draw the first two compounds in a bond-line formula. Draw the
second two compounds in a condensed formula.

(CH3)3CCH2CH2CH(CH3)2
CH3CH2C(CH3)2CH(OH)CH2CH2CH2Cl

OH

OH
Br
 Cl
OH

(CH3)3CCH2CH2CH(CH3)2 CH3CH2C(CH3)2CH(OH)CH2CH2CH2Cl

(CH3)2CHCH2C(CH3)2CH(OH)CH(Br)CH3
OH
OH
CH
H 2C CH2 OH
Br
H 2C CH2
CH2
 Lewis structures of some compounds.
Cl
Cl C Cl O
Cl H C H H C C H

CCl4 CH2O C 2 H2

H
H H H
H C O H H C C C H H C N
H H
CH3OH CH3CHCH2 HCN
 Lewis Structures
• Bonding electrons
• Nonbonding electrons or lone pairs
H
H
H C O
H

Satisfy the octet rule! =>

 Lewis Structures
H
H-O-H H-N-H H-C-H H-Cl
H H
H 2 O (8) N H 3 (8) CH 4 (8) HCl (8)
Water Ammonia Meth ane Hyd rogen ch loride
H H H O
C C H-C C-H C O H C H
O O
H H H
C2 H 4 (12) C2H 2 (10) CH 2O (12) H 2CO 3 (24)
Ethylene Acetylen e Formald ehyde Carbonic acid

• In neutral molecules
– hydrogen has one bond.
– carbon has 4 bonds and no lone pairs.
– nitrogen has 3 bonds and 1 lone pair.
– oxygen has 2 bonds and 2 lone pairs.
– halogens have 1 bond and 3 lone pairs.
 Isomers
Different compounds with the same
formula but different molecular structure.

• Example: C4H10
CH3
CH3–CH2-CH2-CH3 or CH3 – CH – CH3
Types of isomers
Section 20.1
Saturated Hydrocarbons

Structural Formulas and Isomerism

• Structural isomerism – occurs when 2 molecules have the

same atoms but different bonds
 Stereochemistry

A comparison of consitutional isomers

and geometric stereoisomers

Stereoisomers may be geometric (cis/trans) or optical.

Cis-Trans Isomerism in Cycloalkanes
◼ Rotation about C-C bonds in cycloalkanes is limited by the
ring structure
◼ There are two different 1,2-dimethyl-cyclopropane
isomers, one with the two methyls on the same side (cis)
of the ring and one with the methyls on opposite sides
(trans)
Stereoisomers
◼ Compounds with atoms connected in the same order but which
differ in three-dimensional orientation, are stereoisomers
◼ The terms “cis” and “trans” should be used to specify
stereoisomeric ring structures
◼ Recall that constitutional isomers have atoms connected in
different order
 Br

Br Br Br
trans cis

Br Br

Br
Br Br Br

cis Br
Br trans
Br Br

Br
Br Br
Br
cis Br
Br trans

Br Br Br
Br
Br
Br
Br Br
cis trans