Return to Contents Chapter 3: Conformations of Alkanes and Cycloalkanes  Ch 3 contents

Cycloalkanes

The most stable conformations of the first three cycloalkanes (the smallest three) are shown below where they can be contrasted with the planar conformation. In order to be able to compare the strain in each member of the cycloalkane series, the heat of combustion per methylene (i.e. -CH2-) is also given (see note below the table). The smaller this number is the less ring strain there is.
In each case, you should manipulate the 3D-JSMOL images to visualise the deviation from planarity and the effect this has on the eclipsing interactions of adjacent C-H bonds and C-C bonds (hint turn the model to "see" the Newman projections).

 
planar
most stable structure  
C3H6
cyclopropane
CYCLOPROPANE
ΔHc / CH2 = -697 kJ/mol
(-166.6 kcal/mol)
see left
       
C4H8

CYCLOBUTANE
ΔHc / CH2 = -681 kJ/mol
(-
162.7 kcal/mol)
       
C5H10
cyclopentane
CYCLOPENTANE
ΔHc / CH2 = -658 kJ/mol
(-
157.3 kcal/mol)
 
Note: since the structures are not isomeric, we can't just compare the heats of combustion. However, simple cycloalkanes have have the generic molecular formula (CH2)n, where n = the number of C atoms in the ring. Therefore dividing the heat of combustion for each cycloalkane by n means we are able to make a reasonable comparison.


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organic chemistry © Dr. Ian Hunt, Department of Chemistry University of Calgary