Cyclohexylamine

Definition

Cyclohexylamine is an organic compound with the chemical formula C$_6$H$_{11}$NH$_2$. It is a primary amine derived from the cyclic hydrocarbon cyclohexane, and it exhibits the characteristic properties of aliphatic amines, including basicity and nucleophilicity.

5 Must Know Facts For Your Next Test

1. Cyclohexylamine is a colorless liquid with a distinctive amine-like odor and is miscible with water and many organic solvents.
2. The basicity of cyclohexylamine is influenced by the electron-donating effects of the cyclohexyl group, which increases the electron density around the nitrogen atom and enhances its ability to accept a proton.
3. Cyclohexylamine is commonly used as a precursor in the synthesis of various pharmaceuticals, agrochemicals, and other specialty chemicals.
4. The pKa of cyclohexylamine is approximately 10.7, indicating that it is a moderately strong base that can be protonated in acidic environments.
5. Cyclohexylamine is known to undergo various organic reactions, such as acylation, alkylation, and condensation reactions, due to the nucleophilic nature of the amino group.

Review Questions

• Explain how the basicity of cyclohexylamine is influenced by the presence of the cyclohexyl group.
  • The cyclohexyl group in cyclohexylamine is an electron-donating substituent, which increases the electron density around the nitrogen atom. This enhanced electron density makes the nitrogen more basic, as it is better able to accept a proton to form a conjugate acid. The basicity of cyclohexylamine is therefore increased compared to simpler aliphatic amines due to the stabilizing effect of the cyclohexyl group.
• Describe the nucleophilic reactivity of cyclohexylamine and provide an example of a reaction it may undergo.
  • Cyclohexylamine is a nucleophilic species due to the presence of the lone pair of electrons on the nitrogen atom. This nucleophilicity allows cyclohexylamine to participate in various organic reactions, such as acylation. For example, cyclohexylamine can react with an acyl chloride, like acetyl chloride, to form an amide product through a nucleophilic acyl substitution reaction. The amino group of cyclohexylamine acts as the nucleophile, attacking the carbonyl carbon of the acyl chloride and displacing the chloride ion.
• Analyze the importance of cyclohexylamine as a precursor in the synthesis of various chemical products and discuss how its properties contribute to its utility.
  • Cyclohexylamine is a valuable precursor in the synthesis of many pharmaceuticals, agrochemicals, and other specialty chemicals. Its importance is derived from the unique combination of its chemical properties, including basicity and nucleophilicity. The basicity of cyclohexylamine allows it to participate in acid-base reactions, while its nucleophilicity enables it to undergo a variety of condensation, alkylation, and acylation reactions. These versatile reactivity patterns make cyclohexylamine a versatile building block for the construction of more complex molecules with diverse applications in the chemical industry.

Related terms

Aliphatic Amine: Aliphatic amines are organic compounds containing a nitrogen atom bonded to one or more alkyl or cycloalkyl groups, as opposed to aromatic amines which contain a nitrogen atom bonded to an aromatic ring.

Nucleophilicity:

Nucleophilicity is a measure of the reactivity of a nucleophile, which is a species that donates an electron pair to form a new chemical bond in a reaction.

Basicity:

Basicity refers to the ability of a chemical species to accept a proton, forming a conjugate acid, and is an important property in determining the behavior of amines in chemical reactions.