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Conformations

Basic Organic Chemistry

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Learning Outcomes:

1. Learn how to draw the


Newman Projection and
the Chair Conformation
and its Ring Flip.

2. Rank the stability of


Newman Projections and
Chair Conformations. 2
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Conformation is the
various positions
available to a
molecule.
Why is this important
to know?
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Conformation is
important to be able to
predict the positions
available to molecules
because there are
certain activities that
can be performed only in
specific conformations.6
If the molecule cannot
twist into the
conformation necessary
for a reaction to take
place, then the reaction
will not happen.
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Two different styles to show
conformations:

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Wedges and Dashes

Wedge Dash
(coming (going away
out in at the back)
front)

Let us have a short and simple exercise.  9


How to draw the Newman
Projection?

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How to draw the Newman
Projection?

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How to draw the Newman
Projection?

Sometimes, you can see all six groups because they


are staggered. But other times, you can’t see the
groups in the back because they are being eclipsed by
the three groups in the front. 12
Practice 1. Draw a Newman
projection of the following
compound looking from the
perspective of the arrow:

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1

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Ranking the Stability of
Newman Projection
Ex. Conformations of Butane – STAGGERED CONFORMATION

The methyl groups are as far away from each other as possible, which
is the most stable conformation, called the anti conformation. The
other two drawings both have the methyl groups near each other in
space. This interaction is called a gauche interaction, which makes
these conformations a little bit less stable than the anti
15 conformation.
Ranking the Stability of
Newman Projection
Ex. Conformations of Butane – ECLIPSED CONFORMATIONS

These conformations are all high in energy relative to the


staggered conformations. All of the groups are eclipsing each
other, so they are very crowded. But the middle one is the
most unstable, because the two methyl groups (the two
largest groups) are eclipsing each other.
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To summarize Newman
Projection:
 The most stable conformation will
be the staggered conformation
where the large groups are as far
apart as possible (anti).

 The least stable conformation will


be the eclipsed conformation where
the large groups are eclipsing each
other. 17
The CHAIR CONFORMATION
(for 6-membered rings)

The chair conformation


is ONLY applicable to
six-membered rings or
compounds like the
cyclohexane.

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How to draw the Chair
Conformation:
1 2

3 4

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Please don’t ever draw a chair like this:

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The Chair with the
Substituents

These six substituents are called axial


substituents. They go straight up and
down, in the order shown above. 21
The Chair with the
Substituents

Equatorial substituents are the substituents


pointing out toward the sides. There are also six of
them. Each one is drawn so that it is parallel to
the two bonds from which it is once removed.
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Placing Groups on the
Chair

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Placing Groups on the
Chair

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Practice: Draw a chair
conformation of the compound
below.

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Answer:

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Ring Flipping

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It is not simply turning the ring over!

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How to Draw Ring Flips
Draw the normal chair conformation:

Draw the flipped chair conformation:

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Practice: Draw the ring flip of the
following compound.

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Answer:

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To summarize Ring Flip:

1.

2. Molecules or atoms attached


to the ring MUST be same in the
ring flip. 32
Comparing the Stability
of Chair Conformation
Important note: A chair will be more
stable with a group in an equatorial
position, because it is not bumping
into anything (this bumping is called
steric hindrance). Axial positions are
bumping into other axial positions, but
equatorial positions are not.
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End of Presentation
Source: Klein, D. Organic Chemistry I.
Translating the Basic Concepts. 2nd
ed. USA: John Wiley & Sons, Inc.
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