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BRIEF NOTE ON THE GIVEN TOPIC

Cycloalkanes are a saturated cyclic structure having sp3 carbon and hydrogen.  It contains only carbon-carbon single Bond and represented by common formula CnH2n, Where c represents a carbon atom, and n is the number of carbon in the cyclic structure. Carbon can be either 2 or 3 n the cycloalkane. Cycloalkane size ranges from 3 carbons to more than 25 carbons. For the nomenclature of cycloalkanes, cyclo has to be used as a prefix, followed by the name of the open chain hydrocarbon. If substituents are present in the molecule, the nomenclatures will start with substituents giving priority to the substituents with lower alphabetical order. Cyclopropane used to be highly unstable due to ring strain as in the cyclopropane molecule. As in the cyclopropane, carbon atoms are sp3 hybridised, having a tetrahedral bond angle of 109° 28, while due to cyclic structure calculated bond angle is 60°. Cyclopropane shows significant deviation from 109° to 60° which caused a ring strain or angle strain and instability in the molecule (having high potential energy). The ring strain is computed to be around 120 kJ mol-1. Angle strain is strain created when a bond angle in a molecule is either more or less than expected bond angle.

expected bond angle.jpg

Cyclobutane is having a square structure having a bond angle of 90°. It shows a puckered structure which reduces the eclipsing interactions between hydrogen atoms. The ring strain is computed to be around 110 kJ mol-1 (slightly more stable than cyclopropane).

Cycloalkane having 5-6 carbon used to be more stable, and it occurs naturally as it contains minimum angle strain (having lower potential energy as less deviation from the tetrahedral bond

Similarly, cyclopentane is having a bond angle of 108° which is near to the tetrahedral bond angle. It shows a torsional strain of approximately 42 kJ mol-1 only. Cyclopentane molecule used to adopt envelop conformation to increase the stability in which 4 carbon atoms lies in a plane and the 5th carbon bent out of the plane. In the envelope conformation, cyclopentane reduces the eclipsed interactions of hydrogen which result in the lower torsional strain in the molecule. By adopting this structure, it also reduces its ring strain to 42 kJ mol-1.

Cyclohexane adopts also adopts the number of puckered conformations to increase its stability and lower the angle strain.

Cyclohexane.jpg

Chair conformation is the most stable structure in cyclohexane in which bond angles are near to 109.5° leads to the minimum angle strain. Hydrogen atoms on adjacent carbons are in staggered conformation with minimum torsional strain. There are two kinds of orientation in hydrogen molecule containing equatorial bonds (parallel to C-H bond) and axial bonds (perpendicular to CH bond).

CH bond.jpg

2nd most stable conformation is twisted boat structure which is nonplanar conformations. In boat structure, it has torsional strain due to eclipsed interactions between 4 hydrogen molecule, and steric strain due to flagpole interactions of 2 hydrogen molecule.

Chair and boat conformations are differing in the stability by 27 kJ mol-1, at room temperature, approximately 99.99%. That's why most of the cyclohexane molecules adopt the chair conformation at room temperature.

Cycloalkane and alkanes are one of the essential constituents in natural gas, petroleum gas. It used to be in gaseous form at room temperature.

Cycloalkane is a highly stable molecule. It showed free radical reaction as well as SN (nucleophilic substitution type of reaction).

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