Cyclohex-2-en-1-one

Definition

Cyclohex-2-en-1-one is a cyclic enone compound, consisting of a six-membered carbon ring with a ketone group at one position and a carbon-carbon double bond at an adjacent position. This structural feature makes it a key reactant in the context of conjugate nucleophilic addition reactions.

5 Must Know Facts For Your Next Test

1. Cyclohex-2-en-1-one is a cyclic enone, meaning it contains both a carbonyl group and a carbon-carbon double bond in a cyclic structure.
2. The conjugated nature of the carbonyl and alkene makes cyclohex-2-en-1-one susceptible to nucleophilic attack at the β-carbon through conjugate addition reactions.
3. Conjugate nucleophilic addition to cyclohex-2-en-1-one typically results in the formation of a new carbon-carbon bond, while the carbonyl group remains intact.
4. The reactivity of cyclohex-2-en-1-one in conjugate addition reactions is influenced by the electron-withdrawing nature of the carbonyl group, which makes the β-carbon more electrophilic.
5. Successful conjugate addition to cyclohex-2-en-1-one can be used to synthesize a variety of cyclic compounds with diverse functional groups.

Review Questions

• Explain the structural features of cyclohex-2-en-1-one that make it susceptible to conjugate nucleophilic addition reactions.
  • Cyclohex-2-en-1-one contains both a carbonyl group and a carbon-carbon double bond in a cyclic arrangement, creating a conjugated system. The electron-withdrawing nature of the carbonyl group makes the β-carbon more electrophilic, allowing it to undergo nucleophilic attack through a conjugate addition mechanism. This reactivity is crucial in the context of 19.13 Conjugate Nucleophilic Addition to α,β‑Unsaturated Aldehydes and Ketones.
• Describe the typical outcome of a conjugate nucleophilic addition reaction involving cyclohex-2-en-1-one.
  • In a conjugate nucleophilic addition reaction with cyclohex-2-en-1-one, the nucleophile typically adds to the β-carbon of the enone, forming a new carbon-carbon bond. The carbonyl group remains intact, allowing for the synthesis of a variety of cyclic compounds with diverse functional groups. This type of reactivity is important in the context of 19.13 Conjugate Nucleophilic Addition to α,β‑Unsaturated Aldehydes and Ketones, where cyclohex-2-en-1-one can serve as a key substrate.
• Analyze how the electronic properties of cyclohex-2-en-1-one influence its reactivity in conjugate nucleophilic addition reactions, and discuss the significance of this reactivity in the broader context of 19.13 Conjugate Nucleophilic Addition to α,β‑Unsaturated Aldehydes and Ketones.
  • The conjugated nature of the carbonyl group and carbon-carbon double bond in cyclohex-2-en-1-one creates an electron-deficient β-carbon that is susceptible to nucleophilic attack. The electron-withdrawing effect of the carbonyl group increases the electrophilicity of the β-carbon, making it a prime target for conjugate addition reactions. This reactivity is crucial in the context of 19.13 Conjugate Nucleophilic Addition to α,β‑Unsaturated Aldehydes and Ketones, as it allows for the synthesis of a wide range of cyclic compounds with diverse functional groups through strategic nucleophilic addition to cyclohex-2-en-1-one and other similar α,β-unsaturated carbonyl substrates.

Related terms

Conjugate Addition: A nucleophilic addition reaction that occurs at the β-carbon of an α,β-unsaturated carbonyl compound, rather than the carbonyl carbon.

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

Nucleophile: A species that donates an electron pair to form a new covalent bond, typically a negatively charged ion or a neutral molecule with a lone pair of electrons.