Cyclohexane

Definition

Cyclohexane is a cyclic hydrocarbon compound with the chemical formula C₆H₁₂. It is a colorless, flammable liquid that is widely used as a solvent and in the production of various chemicals.

5 Must Know Facts For Your Next Test

1. Cyclohexane is a six-membered ring with all carbon atoms in a chair conformation, which is the most stable configuration.
2. The carbon-carbon bond lengths in cyclohexane are approximately 1.54 Å, and the bond angles are close to 109.5°.
3. Cyclohexane is a nonpolar molecule due to the symmetric arrangement of its carbon and hydrogen atoms.
4. Cyclohexane is commonly used as a solvent in organic synthesis, as a raw material for the production of adipic acid, and in the manufacture of nylon.
5. Cyclohexane can undergo various reactions, including hydrogenation, halogenation, and oxidation, due to the reactivity of its carbon-hydrogen bonds.

Review Questions

• Explain the significance of the chair conformation of cyclohexane and how it contributes to the stability of the molecule.
  • The chair conformation of cyclohexane is the most stable configuration because it minimizes the steric strain and maximizes the number of equatorial positions, which are more favorable for the bulky substituents. In the chair conformation, the carbon-carbon bonds are oriented in a way that reduces the repulsive interactions between the hydrogen atoms, resulting in a more stable and lower-energy arrangement compared to other possible conformations.
• Describe the reactivity of cyclohexane and how it can undergo various chemical transformations.
  • Cyclohexane is a relatively unreactive alkane due to the stability of its carbon-hydrogen bonds. However, it can undergo reactions such as halogenation, where the hydrogen atoms can be substituted by halogen atoms (e.g., chlorination or bromination), as well as oxidation reactions that can lead to the formation of more complex organic compounds. Additionally, cyclohexane can be hydrogenated to produce other cyclic alkanes or undergo ring-opening reactions to form linear alkanes, demonstrating its versatility in organic synthesis.
• Analyze the importance of cyclohexane in the context of 20.1 Hydrocarbons and its applications in the chemical industry.
  • As a cyclic hydrocarbon, cyclohexane is an essential component in the study of 20.1 Hydrocarbons. It serves as a model compound for understanding the properties and behavior of cyclic alkanes, which are a significant class of hydrocarbons. Cyclohexane's widespread use as a solvent and its role as a precursor in the production of various chemicals, such as adipic acid for nylon synthesis, highlight its importance in the chemical industry. Understanding the structure, reactivity, and applications of cyclohexane is crucial for comprehending the broader concepts of hydrocarbon chemistry and their practical relevance.

Related terms

Alkanes: Saturated hydrocarbons with the general formula CnH2n+2, where n is the number of carbon atoms.

Conformations: The different three-dimensional arrangements that a molecule can adopt without breaking any bonds.

Aromaticity: The property of certain cyclic compounds that exhibit increased stability and specific chemical behaviors.