Chapter 3:
Conformations of Alkanes and Cycloalkanes 
Ch 3 contents

Higher Alkanes

The same basic ideas of conformational analyzis developed previously for simple alkanes also apply, but some new situations are encountered.

Butane: CH3-CH2-CH2-CH3

In butane it is the rotation about the C2-C3 bond that is of most interest since the relative position of the two methyl groups is important. 

This can be seen most easily by rotating the molecule to view it down the C2-C3 bond. 

The more important conformations are shown below:

ANTI
a staggered conformation with the Me groups at 180o with respect to each other. This is the most stable conformation since the Me groups are as far apart as possible.
anti conformation of butane
GAUCHE
a staggered conformation with the Me groups at 60o with respect to each other.
gauche conformation of butane
SYN
an eclipsed conformation with the Me groups at 0o with respect to each other. This is the least stable conformation due to the steric strain caused by the proximity of the Me groups and the torsional strain of the eclipsed bonds.
syn conformation of butane
GAUCHE
a staggered conformation with the Me groups at 60o with respect to each other
gauche conformation of butane
 
 
 
note: the two gauche conformations are not quite the same, try to convince yourself of this.
How are they related to each other ?non-superimposable mirror images

Question
Hydrocarbons are often drawn as simple "zig-zag" structures an example of which is given below.  What type of conformation  does this represent ? anti (which is the most stable)
 


a zig-zag representation of C6H14, n-hexane


 



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