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Buoi5 Sep20 Chapter7 Full

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20 views45 pages

Buoi5 Sep20 Chapter7 Full

Uploaded by

tloc18192006
Copyright
© © All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
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CHAPTER 7

CONFIGURATION
INTRODUCTION
It is possible for a molecule to have a region where
there are two possibilities for how the atoms can be
connected in 3D space, much like the difference
between a right hand and a left hand.

Instead of “right hand” and “left hand,” we call the two


possibilities R and S. When we talk about the
configuration of a compound, we are talking about
whether it is R or S.
INTRODUCTION
Conformations are the different positions that a
molecule can twist into, but configuration is a matter
of right-handedness or left-handedness (R or S).
INTRODUCTION
In molecules, the regions that can be R or S are called
stereocenters (or chiral centers—chiral is Greek for
“hand,” and we can understand the symbolism there)
7.1. LOCATING STEREOCENTERS
A stereocenter is defined as a carbon atom with four
different groups on it.
7.1. LOCATING STEREOCENTERS
Anytime you have four different groups connected to a
carbon atom, there will be two ways to arrange the
groups in space (always two; never more and never
less). These two arrangements are different
configurations:
EXERCISES:
In each of the compounds below, there is one
stereocenter. Find it.
7.2. DETERMINE THE CONFIGURATION OF A
STEREOCENTER
7.2. DETERMINE THE CONFIGURATION OF A
STEREOCENTER

When comparing the four atoms in the example above, we


see that oxygen has the highest atomic number, so we
give it the first priority - we give it the number 1. Hydrogen
is the smallest atom, so it will always get the number 4
(lowest priority) when a stereocenter has a hydrogen atom.
7.2. DETERMINE THE CONFIGURATION OF A
STEREOCENTER
7.2. DETERMINE THE CONFIGURATION OF A
STEREOCENTER
7.2. DETERMINE THE CONFIGURATION OF A
STEREOCENTER
7.2. DETERMINE THE CONFIGURATION OF A
STEREOCENTER
7.2. DETERMINE THE CONFIGURATION OF A
STEREOCENTER
7.2. DETERMINE THE CONFIGURATION OF A
STEREOCENTER
If the number 4 group is pointing away from us (on the
dash), then we ask whether 1, 2, and 3 are going
clockwise or counterclockwise:
7.2. DETERMINE THE CONFIGURATION OF A
STEREOCENTER
If the number 4 group is pointing away from us (on the
dash), then we ask whether 1, 2, and 3 are going
clockwise or counterclockwise:
7.2. DETERMINE THE CONFIGURATION OF A
STEREOCENTER
when the number 4 is not on a dash, we need to rotate
the molecule so that the fourth priority is on a dash. To
do this, imagine spearing the molecule with a pencil
and then rotating the pencil 90°:
7.2. DETERMINE THE CONFIGURATION OF A
STEREOCENTER
when the number 4 is not on a dash, we need to rotate
the molecule so that the fourth priority is on a dash. To
do this, we spear the molecule with a pencil and rotate
180° to put the 4 on a dash:
EXERCISES:
EXERCISES:
EXERCISES:
EXERCISES:
7.3. NOMENCLATURE
7.3. NOMENCLATURE
7.3. NOMENCLATURE

(3R,4S)-3,4-dimethylhexan-2-one
7.3. NOMENCLATURE
There are still two possible stereoisomers, but we
cannot use the cis/trans system here.
7.3. NOMENCLATURE
There are still two possible stereoisomers, but we
cannot use the cis/trans system here.
7.3. NOMENCLATURE
There are still two possible stereoisomers, but we
cannot use the cis/trans system here.
7.3. NOMENCLATURE
There are still two possible stereoisomers, but we
cannot use the cis/trans system here.
7.3. NOMENCLATURE
There are still two possible stereoisomers, but we
cannot use the cis/trans system here.
7.3. NOMENCLATURE
There are still two possible stereoisomers, but we
cannot use the cis/trans system here.
7.3. NOMENCLATURE
There are still two possible stereoisomers, but we
cannot use the cis/trans system here.
7.3. NOMENCLATURE
The same side is called Z (for the German word
“zusammen” meaning together), and opposite sides
are called E (for the German word “entgegen” meaning
opposite).
7.3. NOMENCLATURE
Name the following compound, including
stereochemistry in the beginning of the name.
7.3. NOMENCLATURE
Name the following compound, including
stereochemistry in the beginning of the name.
7.4. ENANTIOMER
when you have two compounds that are non-
superimposable mirror images, they are called
enantiomers. Each one is the enantiomer of the other.
Together, they are a pair of enantiomers.
7.4. ENANTIOMER
The simplest way to draw an enantiomer is to redraw
the carbon skeleton but invert all stereocenters. In
other words, change all dashes into wedges and
change all wedges into dashes. For example,
7.4. ENANTIOMER
The simplest way to draw an enantiomer is to redraw
the carbon skeleton but invert all stereocenters. In
other words, change all dashes into wedges and
change all wedges into dashes. For example,
7.4. ENANTIOMER
Draw the enantiomer of the following compound:
7.5. DIASTEROMERS
Let’s start off with a simple case where we only have
two stereocenters. Consider the two compounds below:
7.5. DIASTEROMERS
Diastereomers are any compounds that are
nonsuperimposable stereo- isomers that are not mirror
images of each other.
7.5. DIASTEROMERS
E/Z isomers (or cis/trans isomers) are called
diastereomers, because they are stereoisomers that
are not mirror images of each other:
7.6. MESO COMPOUNDS
A meso compound has stereocenters, but the
compound also has symmetry that allows it to be the
mirror image of itself.
7.6. MESO COMPOUNDS
It can also happen when the compound has a center of
inversion. For example,
7.6. MESO COMPOUNDS
Identify which of the following compounds is a meso
compound.

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