The torsional strain is also known as Pitzer strain. The Pitzer strain in the cyclobutane molecule is experienced when the atoms or the substituents are in the eclipsed form. Due to the eclipsed form in a molecule, the atoms or the substituents are in the same molecular plane. The atoms possess an electronic cloud around them which repels the electronic field around the other atoms. The state where the atoms repel each other, leads to the increment of the potential energy of the molecule. The molecule is in strained state. The strain that is experienced by the molecule due to the superposition of the atoms over each other is called Pitzer strain. The torsional strain in cyclobutane along with the other strain in cyclobutane are discussed in the following subtopics. Apart from that, the torsional strain experienced in the other cycloalkanes is explained in brief.
The torsional strain in the cyclobutane is experienced due to the eclipsed form of the cyclobutane molecule. The overlapping arrangement around the carbon atom in back and forth position in Newmann projection depicts the steric hindrance among the electronic cloud of the substituent atoms. In cyclobutane, the extent of Pitzer strain is very less as the cyclobutane molecule attains a butterfly like orientation in its eclipsed form. The Pitzer strain in simple word can be explained as the repulsion among two atoms, which are three covalent bonds apart. In case of the eclipsed form of the cyclobutane molecule, the carbon atoms in the back and forth position are far apart than the conventional carbon-carbon distance. This allows the other substituents to situate freely in the three-dimensional space with minimum Pitzer or torsional strain. The cyclobutane molecule has less torsional strain. The molecule is high in its reactivity which is due to the angle strain present in the molecule.
The cyclopentane ring experience some sort of Pitzer strain. The cyclopentane molecule has five carbon atoms in the main ring and the hydrogen attached to these carbons repel each other which is a consequence of the Pitzer strain. The cyclopentane molecule attains an envelope shape in order to avoid steric repulsion of the electronic cloud around the hydrogen atom. One of the carbon atoms is raised from the molecular plane which resembles like a flap of the envelope. The adjacent carbon atoms around the carbon atom, which is raised from the molecular plane, and are pointing downwards in order to have minimum interaction among the substituents with that of the carbon atom acting as flap of the envelope. The cyclopentane molecule is more reactive than cyclohexane molecule which is due to the angle strain present in the cyclopentane ring.
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