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Mirror, Mirror, on the Wall

A Study in Chirality
Do You Know...
 what an isomer is?  Isomers are
different
compounds that
 how many kinds of have the same
isomers there are? molecular formula.
(Hint – use your
textbook index.)  There are
conformational,
constitutional
(structural), and
stereoisomers.
Conformational Isomers
 Parts of the molecule rotate
freely around a single bond
but do not change location on
the molecule.
 These isomers will not have
different physical or chemical
properties, since they can
change their shape easily.
Conformational Isomers

 All of these images


are 1-propanol
arranged in different
conformations.
 The order of
attachment is the
same in all.
Constitutional Isomers

 Constitutional isomers have the same


molecular formula, but the groups and/or
atoms are attached to the molecule in a
different order.
 Constitutional isomers may also have
different kinds of bonds within the
molecules.
Constitutional Isomers

 C3H7Cl can be either 1-chloropropane or 2-


chloropropane.

H H H H Cl H
| | | | | |
Cl—C—C—C—H H—C—C—C—H
| | | | | |
H H H H H H
Constitutional Isomers
 C3H6O can have two different structures.
 What are the names of these compounds?
H H H H
| | \ |
O=C—C—C—H C=C—C—OH
| | | / | |
H H H H H H

 The first compound is called propanal. The


second compound is 2-propen-1-ol.
Stereoisomers

 In stereoisomers the atoms and/or groups


are attached to the molecule in the same
order, but they have a different orientation
in space.
 There are several different types of
stereoisomers. We have already studied
one type.
Cis and Trans Isomers
 Recall from Chapter 12 (Section 12.2)
that alkenes can exist as cis and trans
isomers.
 Cis and trans isomers are one type of
stereoisomer.
 They have the same atoms and/or
groups, but they are attached to
different sides of the double bond.
 This structure is a
cis isomer, with
the groups both on
the same side of
the double bond in
the molecule.
 And this is a trans
isomer, with the
groups on opposite
sides of the double
bond.
Can You Match These?
D A
 Trans-2-pentene___
 Trans-2-methyl-3-
hexene ___
C
B
A
 Cis-2-butene ___
 B
Cis-2-pentene ___

D C
Stereoisomers
 We will now begin
to explore isomers
based on the groups
around specific
carbon atoms
within a molecule.

This chapter will be taught by YOU


using Power Point presentations!
Your Group Tasks
 You will work in groups of
three students, with each
member of the group
contributing to the
presentation.
 Each group will be
assigned a different
concept from within this
chapter.
Your Group Tasks
 You will use your textbook and Internet
resources to gather information on your
assigned topic.
 Each group will make and photograph
molecular models illustrating your
topic. You may also use images from
other sources with appropriate
permission.
Your Group Tasks
 Each group will create
and present a Power
Point presentation that
teaches about their
assigned topic.
 Complete details for
the project will be
found on your
handout.
Individual Responsibilities
 Each student is
responsible for learning
the vocabulary from the
entire chapter.
 Each student is
responsible for learning
the material presented by
their group and by the
other groups.
Individual Responsibilities
 Each student is
responsible for learning
any material presented
by the teacher.
 Each student will be
individually assessed by
written and
manipulative tests.

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