ich represents the ring flip of the following structure?

OH

Me

A.

B.

Me

OH

D.

Me

OH

C.

OH

OH
Me

Me

E.

Me
OH

F.
Me

OH

So far

Bonding and structure

Hybridization
Acid-base equilibrium
pKas
Resonance
Nomenclature (alkanes, cycloalkanes, alkyl halides)
Functional groups
Alkanes and cycloalkanes (properties)
Constitutional isomers
Newman projections
Chair conformations

Exam 1 on October 9!

Bonds in Cyclohexane
Chair conformation:
Bond angles of 111o
All C-C bonds are staggered
Each C has an equatorial and an axial bond (C-H)

After a ring flip (conformational inversion): all axial

4
bonds become equatorial and vice-versa.

The Conformations of Cyclohexane

Boat Conformation of Cyclohexane

Bonds are in eclipsed conformations
Significantly less stable than chair

Conformational Analysis of
Monosubstituted Cyclohexanes

1
3

2
7

1,3-Diaxial Interactions

Disubstituted Cycloalkanes

Stereoisomerism
Stereoisomers: isomers that differ only by the 3D
arrangements of the atoms
Have the same type and numbers of bonds
Conformational isomers
Cis-Trans (geometric) isomers: different 3D arrangement of
atoms with reference to a molecular plane.
1,2-Disubstituted cyclohexanes have geometric isomers
1,31,4-

Ring flipping does not interconvert geometric isomers!

10

What is the relationship between the two cyclohexane chairs

below?

A) conformational isomers
B) constitutional isomers
C)geometric isomers
D)not isomers

Cyclic systems in nature

Diamonds

4.15 Polycyclic Systems

There are many biologically important

steroids, all of which involve fusing
cycloalkanes as part of their structure.

Copyright 2012 John

Wiley & Sons, Inc.

Klein, Organic Chemistry 1e

4 -13

IUPAC Nomenclature of Alkenes

The parent chain must include the double bond
Numbering of the parent chain is done to give the
smallest number to the double bond C
The double bond has priority over halogens and
alkyl groups

14

IUPAC Nomenclature of Cycloalkenes

Cyclopentene
1-Methylcyclohexene

3-Chlorocycloheptene

Monosubstituted cycloalkene: no number needed

to indicate the position of double bond carbons
The number of the ring C starts at the double
bond (the double bond connects C1 and C2)
15

E, Z Nomenclature of Geometric Isomers

Assign priorities to the two groups on each carbon atom

1. Determine the atomic number of the atoms directly

bonded to the sp2 carbons.

Higher atomic number, higher priority

2. If there is a tie, consider the atoms attached to the tied

atoms (priority is assigned at the first point of difference)
3. Multiple bonds are treated as attachment of multiple
single bonds
16