Conformational Analysis 2 PDF
Conformational Analysis 2 PDF
Conformational Analysis 2 PDF
Destabilization of a molecule caused by the eclipsing of bonds on adjacent atoms is called torsional
strain.
A C E G
All staggered conformations
have less energy than all
eclipsed conformations.
Staggered are free of
torsional strain thus more
stable
B D F
There are 2 types of staggered conformations in butane:
1) Gauche: B (60°) and F (300°)
2) Anti: D (180°)
In gauche conformations the two methyl groups are close enough to each other that courses steric strain (less
stable than anti)
In anti conformation the two methyl groups are farthest away from each other and contain no steric strain, thus
most stable.
Conformational Analysis of Butane
https://video.search.yahoo.com/search/video?fr=mcafee&p=ring+strain
#action=view&id=1&vid=b7226381c5313657ca56980a35009cfb
Bond angle: 120ᵒ
Planar conformer
All 12 C-H bonds
are eclipsed
(unstable)
Preferred conformation in
which cyclohexane systems
exist in.
Looking at the chair
conformation, one can
identify a back-rest, a seat
and a leg-rest like that of a
chair.
1. The C—C bond angles are all 109.5° ⇒ free of angle strain.
2. Chair cyclohexane is free of torsional strain:
3. When viewed along any C—C bond, the atoms are seen to be
perfectly staggered.
4. The hydrogen atoms at opposite corners (C1 and C4) of the
cyclohexane ring are maximally separated.
• Boat conformations are also possible with cyclohexane
systems, but they are of higher energy than the chair
conformations.
Boat conformation of cyclohexane:
1) Boat conformation of cyclohexane is
free of angle strain.
2) Boat cyclohexane has torsional strain
and flagpole interaction
i) When viewed along the C—C bond on
either side, the atoms are found to
be eclipsed ⇒ considerable torsional
strain.
ii) The hydrogen atoms at opposite
corners (C1 and C4) of the cyclohexane
ring are close enough to cause van der
Waals repulsion ⇒ flagpole interaction.
Of all conformations of cyclohexane, the chair conformations are
of least energy and thus most stable. Chair conformations are
therefore the most realistic representations of cyclohexanes.
There are two types of bonds in cyclohexanes: Equatorial bonds are oriented
towards the rings equator, while axial bonds are on the rings axis.
To ring flip, identify where the substituents are. In one
conformer, push up at C-4 and down at C-1 to obtain the
4C conformer. The other conformer is obtained by
1
pushing up at C-1 and down at C-1 to provide the 1C4
conformer. All equatorial bonds becomes axial and vise
versa when the ring flip.
• In methylcyclohexane, the methyl group can be in an
equatorial or axial position.
• We might, therefore, expect to find two conformers
of methylcyclohexane.
Stability of Cyclohexane Conformer
• Although cyclohexane rings rapidly flip between
conformations at room temperature, the two
conformers of a monosubstituted cyclohexane are not
of equal stability.
A B
• In the 1C4 conformer, there is van der Waals strain (steric) between
hydrogens of the axial CH3 and hydrogens at C-3 and C-5, while in
the 4C1 conformer, there is a smaller van der Waals strain between
hydrogens at C-1 and hydrogens at C-3 and C-5.
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