The key difference between chlorobenzene and cyclohexyl chloride is that chlorobenzene has a delocalized electron cloud, whereas there is no delocalized electron cloud in cyclohexyl chloride.
Chlorobenzene has a benzene ring with a chlorine atom attached to the ring. Here, the chlorine atom has replaced one of the hydrogen atoms in the ring. Therefore, the delocalized electron cloud of the benzene ring is also there. However, cyclohexyl chloride has a chlorine atom attached to a cyclohexane molecule. Here also, the chlorine atom replaces a hydrogen atom of the ring. Since there is no delocalized electron cloud in cyclohexane, cyclohexyl chloride also has no delocalized electron cloud.
CONTENTS
1. Overview and Key Difference
2. What is Chlorobenzene
3. What is Cyclohexyl Chloride
4. Side by Side Comparison – Chlorobenzene vs Cyclohexyl Chloride in Tabular Form
5. Summary
What is Chlorobenzene?
Chlorobenzene is an aromatic organic compound which has a benzene ring with an attached chlorine atom. The chemical formula of this compound is C6H5Cl. It is a colourless and flammable liquid. But it has an almond-like odour. Its molar mass is 112.56 g/mol. Moreover, the melting point of this compound is −45 °C while the boiling point is 131 °C.
When considering the uses of this compound, it is very important as an intermediate in the production of compounds such as herbicides, rubber, etc. Furthermore, it is a high boiling solvent we use in industrial applications.
We can produce chlorobenzene by chlorination of benzene in the presence of Lewis acids such as ferric chloride, and sulfur dichloride. Here, Lewis acid acts as the catalyst for the reaction. It can enhance the electrophilicity of chlorine. Moreover, since chlorine is electronegative, chlorobenzene tends not to undergo further chlorination. More importantly, this compound shows “low to moderate” toxicity. However, if this compound enters our body via breathing, our lungs and urinary system can excrete it.
What is Cyclohexyl Chloride?
Cyclohexyl chloride is an organic compound that has a cyclohexane molecule with one of its hydrogen atoms replaced by a chlorine atom. The chemical formula of it is C6H11Cl. Another common name for this compound is chlorocyclohexane.
Moreover, cyclohexyl chloride is a colourless liquid and has a suffocating odour. Further, we can prepare it by treating cyclohexanol with HCl. Its melting point is −44 °C while the boiling point is 142 °C.
What is the Difference Between Chlorobenzene and Cyclohexyl Chloride?
Chlorobenzene is an aromatic organic compound and has a benzene ring with an attached chlorine atom. Cyclohexyl chloride is an organic compound and has a cyclohexane molecule with one of its hydrogen atoms replaced by a chlorine atom. The key difference between chlorobenzene and cyclohexyl chloride is that chlorobenzene has a delocalized electron cloud, whereas cyclohexyl chloride has no delocalized electron cloud.
Moreover, a further difference between chlorobenzene and cyclohexyl chloride is that the chlorobenzene is aromatic and shows unsaturation, whereas cyclohexyl chloride is non-aromatic, and it has no unsaturation (all the chemical bonds are saturated). When considering the melting and boiling points, for chlorobenzene melting point is −45 °C and the boiling point is 131 °C, while for cyclohexyl chloride melting point is −44 °C and the boiling point is 142 °C.
The below infographic shows more comparisons related to the difference between chlorobenzene and cyclohexyl chloride.
Summary – Chlorobenzene vs Cyclohexyl Chloride
Chlorobenzene is an aromatic organic compound and has a benzene ring with an attached chlorine atom. Cyclohexyl chloride is an organic compound and has a cyclohexane molecule with one of its hydrogen atoms replaced by a chlorine atom. In summary, the key difference between chlorobenzene and cyclohexyl chloride is that chlorobenzene has a delocalized electron cloud, whereas there is no delocalized electron cloud cyclohexyl chloride.
Reference:
1.“Chlorocyclohexane.” National Center for Biotechnology Information. PubChem Compound Database, U.S. National Library of Medicine, Available here.
Image Courtesy:
1. “Chlorobenzene2” By User: Bryan Derksen – Own work (Public Domain) via Commons Wikimedia
2. “Chlorocyclohexane” By Struthious6 at English Wikipedia – Transferred from en.wikipedia to Commons (CC0) via Commons Wikimedia