Cyclohexanone

Definition

Cyclohexanone is a cyclic ketone compound with the molecular formula C₆H₁₀O. It is an important organic compound that is widely used in the synthesis of various chemicals and pharmaceuticals, and it is also a key intermediate in the production of other important compounds.

5 Must Know Facts For Your Next Test

1. Cyclohexanone is a colorless liquid with a characteristic odor, and it is miscible with many organic solvents.
2. It is produced commercially by the oxidation of cyclohexane, which is a common industrial chemical.
3. Cyclohexanone is a key intermediate in the production of adipic acid, a precursor for the manufacture of nylon.
4. It is also used as a solvent in the production of paints, varnishes, and adhesives, as well as in the synthesis of various pharmaceuticals.
5. Cyclohexanone can undergo a variety of chemical reactions, including reduction, condensation, and ring-opening reactions, making it a versatile compound in organic synthesis.

Review Questions

• Explain the relationship between cyclohexanone and the class of organic compounds known as ketones.
  • Cyclohexanone is a specific example of a ketone, which is a class of organic compounds containing a carbonyl group (C=O) bonded to two alkyl or aryl groups. As a cyclic ketone, cyclohexanone has the carbonyl group incorporated into a six-membered ring structure. This structural feature gives cyclohexanone unique chemical properties and reactivity compared to acyclic ketones, making it a valuable intermediate in organic synthesis.
• Describe the role of cyclohexanone in the production of adipic acid, and explain how this relates to the class of organic compounds known as carboxylic acids.
  • Cyclohexanone is a key intermediate in the production of adipic acid, a dicarboxylic acid with the molecular formula C₆H₁₀O₄. Adipic acid is a precursor for the manufacture of nylon, a widely used synthetic polymer. The conversion of cyclohexanone to adipic acid involves a series of oxidation reactions that introduce carboxylic acid functional groups (-COOH) into the molecule. Carboxylic acids are a class of organic compounds characterized by the presence of a carboxyl group, which imparts unique chemical properties and reactivity, making them important in various industrial and biological processes.
• Analyze the versatility of cyclohexanone in organic synthesis, and explain how its ability to undergo a variety of chemical reactions, such as reduction, condensation, and ring-opening reactions, makes it a valuable compound in the context of esters.
  • Cyclohexanone's versatility in organic synthesis is a result of its ability to undergo a diverse range of chemical reactions. For example, the carbonyl group in cyclohexanone can undergo reduction reactions to form alcohols, which can then be further transformed into esters through condensation reactions with carboxylic acids. Additionally, the cyclic structure of cyclohexanone can be opened, allowing for the incorporation of cyclohexanone into larger, more complex molecules. This versatility makes cyclohexanone a valuable intermediate in the synthesis of a wide range of organic compounds, including esters, which are another important class of organic compounds characterized by the presence of a carboxyl group bonded to an alkyl or aryl group.

Related terms

Ketone: A ketone is a functional group that contains a carbonyl group (C=O) bonded to two alkyl or aryl groups.

Cyclohexane: Cyclohexane is a saturated cyclic hydrocarbon with the molecular formula C₆H₁₂.

Oxidation: Oxidation is a chemical reaction that involves the loss of electrons or an increase in the oxidation state of an atom, molecule, or ion.