Chapter 02

Drawing organic molecules

Thinking about molecules in 3D space
Naming alkanes
Newman Projections
Energy of Conformations
Introduction to Isomers
Methane: Simplest organic molecule
Carbon atom with four bonds to hydrogen:

Drawing tetrahedral molecules in 3D space:

Wedges (coming out of the plane of the paper)
Dashes (receding behind the plane of the paper)
Hydrocarbons:
Formulas for alkane molecules (chains of carbon/hydrogen):
How many organic molecules exist?
There are so many ways to connect carbon atoms!
Things to consider:
• Composition
• molecular formula
• Constitution/Connectivity
• constitutional isomers (chapter 2)
• Configuration
• stereoisomers (chapter 4 (double bonds) & chapter 6 (chirality))
• Conformation
• bond rotations: Newman projections (chapter 2)
Skeletal Structures
Carbon and hydrogen atom placement is “implied”
Key point: Carbon always has 4 bonds

CH3

H 3C HC

H 2C CH2

C CH3

H 3C CH3
Quick Rules for Naming Alkanes:
(See Sections 2.4C (7th) or 2.4-2.5 (6th) for more details)

1. Find the longest chain of carbon atoms: base name

If two chains are same length, choose the one with more branches
2. Number carbon atoms to indicate branch positions.
Give the first branch the lowest number possible.
If same from either end, choose the group that’s alphabetically first.
3. Name any branches alphabetically.
Use “di” or “tri” prefixes for branches that occur more than once.

Name structure: locant#,#-prefixabranch-locant#-bbranchbasename

Section 2.4C (7th edition)
Practice: Draw the structures
3-ethyl-4-methyloctane

2,3,4-trimethylhexane
Name the molecules
 Naming Practice

Name the molecule shown.

A 2,3,5-methyl-4-ethylhexane C 3-ethyl-2,4,5-trimethylhexane

B 4-ethyl-2,3,5-trimethylhexane D 4-isopropyl-2,3-dimethylhexane

Respond at pollev.com/sjconnel or in the PollEverywhere app

Cycloalkanes: Ring Structures
Similar rules to straight chain alkanes:
• “1-” is note needed for monosubstituted species
• “First point of difference” – number so that you get the highest
number of branches starting at the lowest number.
• When everything else is equal, chose the first alphabetical group
Draw a skeletal structure or give the name

1-ethyl-2,4-dimethylcyclopentane

3-cyclopentyloctane
Constitutional (structural) Isomers
Same molecular formula, different atom connectivities

C4H10

n-butane isobutane or

2-methylpropane
Classifying Carbon Atoms
Nearly all carbon atoms will have four bonds.

Primary

Secondary

Tertiary

Quaternary
 Types of Carbon atoms

Quick Poll: Identify the highlighted tertiary carbon atom.

B C

D
A
A C

B D
Respond at pollev.com/sjconnel or in the PollEverywhere app
 Identifying Isomers

Which of these is NOT a structural isomer of the others?

A C

B D
Respond at pollev.com/sjconnel or in the PollEverywhere app
Practice
Draw 3 structural isomers of 1,1-dimethylcyclopentane.
Newman Projections
Consider the dihedral angles within the molecule

H H
CH3
H3C
H H
Conformations of molecules
What happens if bonds are freely rotating?
 Br
Newman Projections
Vocabulary for relationships between positions Br
F
Eclipsed
F

Staggered
anti
gauche
Newman Projections
Br
Energies
Br
Discuss in small groups:
Determine which of these represent the same molecule?
Are any of them the same molecule in the same conformation?

Br Cl Br CH3 H3C H
Cl CH3 HO Cl
CH3 Cl
H3C H3C
H 3C OH H Br
H HO H HO Br
CH3