3-(4-methoxyphenyl)cyclohexanone

Definition

3-(4-methoxyphenyl)cyclohexanone is an organic compound consisting of a cyclohexanone ring with a 4-methoxyphenyl substituent at the 3-position. This term is particularly relevant in the context of conjugate nucleophilic addition to α,β‑unsaturated aldehydes and ketones.

5 Must Know Facts For Your Next Test

1. 3-(4-methoxyphenyl)cyclohexanone is an example of an α,β‑unsaturated ketone, where the carbonyl group is conjugated with a carbon-carbon double bond.
2. The 4-methoxyphenyl substituent at the 3-position of the cyclohexanone ring provides additional conjugation and stability to the molecule.
3. Conjugate nucleophilic addition to 3-(4-methoxyphenyl)cyclohexanone involves the attack of a nucleophile at the β-carbon of the α,β‑unsaturated ketone.
4. The presence of the 4-methoxyphenyl group can influence the reactivity and selectivity of the conjugate nucleophilic addition reaction.
5. 3-(4-methoxyphenyl)cyclohexanone is a versatile intermediate in organic synthesis, often used in the preparation of more complex molecules.

Review Questions

• Explain the structural features of 3-(4-methoxyphenyl)cyclohexanone that make it an α,β‑unsaturated ketone.
  • 3-(4-methoxyphenyl)cyclohexanone is an α,β‑unsaturated ketone because it contains a carbonyl group (C=O) that is conjugated with a carbon-carbon double bond. The cyclohexanone ring provides the ketone functionality, while the 4-methoxyphenyl substituent at the 3-position extends the conjugation system, creating the α,β‑unsaturated carbonyl structure.
• Describe the reactivity of 3-(4-methoxyphenyl)cyclohexanone in conjugate nucleophilic addition reactions.
  • In conjugate nucleophilic addition reactions, 3-(4-methoxyphenyl)cyclohexanone undergoes nucleophilic attack at the β-carbon of the α,β‑unsaturated carbonyl system. The presence of the 4-methoxyphenyl group can influence the reactivity and selectivity of the addition, as the substituent can provide stabilization to the intermediate species and affect the overall reaction kinetics and thermodynamics.
• Evaluate the importance of 3-(4-methoxyphenyl)cyclohexanone as an intermediate in organic synthesis, and discuss how its structural features contribute to its versatility.
  • 3-(4-methoxyphenyl)cyclohexanone is a valuable intermediate in organic synthesis due to its versatile reactivity and the ability to incorporate it into more complex molecules. The cyclohexanone ring provides a stable scaffold, while the 4-methoxyphenyl substituent introduces additional functionality and conjugation. These structural features allow 3-(4-methoxyphenyl)cyclohexanone to participate in a variety of reactions, such as conjugate nucleophilic additions, cyclizations, and further functionalization, making it a useful building block for the synthesis of diverse organic compounds.

Related terms

Conjugate Nucleophilic Addition: A type of reaction where a nucleophile adds to the β-carbon of an α,β‑unsaturated carbonyl compound, resulting in the formation of a new carbon-carbon bond.

α,β‑Unsaturated Carbonyl Compounds: Organic compounds containing a carbonyl group (C=O) conjugated with a carbon-carbon double bond.

Cyclohexanone: A cyclic ketone with the formula C₆H₁₀O, commonly used as a building block in organic synthesis.