Conformational isomers

There is free rotation about a !-bond

an infinite array of conformations is possible through
rotation
a conformer is one specific conformation of a molecule
different conformers are isomers - they differ by the
arrangement of atoms in space

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Newman Projection
Conformational isomers are easily
distinguished in a Newman projection
(looking directly down a carbon-carbon bond)

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Staggered vs Eclipsed

eclipsed

staggered

Staggered conformers are more stable (lower in energy)

than eclipsed conformers, due to reduced steric interactions
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Conformers of butane

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15

Conformers of butane

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Conformation of long-chain alkanes

The most stable conformer of long-chain alkanes is
when all anti-staggered conformations are adopted,
leading to a characteristic zig-zag or sawtooth
structure.

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Lipids
Phospholipids are principle components of cell
membranes (lipid bilayer)
contain long alkane chains that stack together
polar groups exposed to aqueous
environment

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Cycloalkanes
Cycloalkanes have a cyclic structure, and general
formula CnH2n
Named by including cyclo prefix

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Cycloalkanes

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Cyclopropane

Cyclopropane is highly
strained, with both
unfavourable bond
angles, and unfavourable
eclipsing interactions

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18

Cyclobutane

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Cyclopentane

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19

Cyclohexane
6-membered rings are strain free, with all C-C-C
angles close to the optimal 109.5 for tetrahedral
geometry, and an all staggered arrangement

This is possible by adopting a chair conformation

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Cyclohexane chair conformation

The chair conformation

results in two types of
hydrogen environments;
axial and equatorial

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Ring-flipping
Two chair
conformations exist
which interconvert by
ring-flipping
ring-flipping
interchanges axial
and equatorial
substituents

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Substituted cyclohexanes
Equatorial substituents result in a more stable
conformation due to decreased steric interactions

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Disubstituted cycloalkanes
Rings prevent free rotation
around single bonds
Isomers can exist when two or
more substituents are attached.
The isomers do not interconvert
(would require breaking of C-C
bonds).
These isomers are
stereoisomers - they differ by the
arrangement of atoms in space
Also called cis/trans isomers,
diastereomers

cis: Latin for same side

trans: Latin for across

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Stereoisomers
Molecules that are non-superimposable mirror-images
are a subclass of stereoisomers
(same bond connectivity but differ in the arrangement
of atoms in space)

Specifically, they are

enantiomers

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