3-phenylbutanal

Definition

3-phenylbutanal is an organic compound that consists of a butanal (4-carbon aldehyde) structure with a phenyl group attached at the third carbon position. It is an important intermediate in organic synthesis and has applications in the fragrance and flavor industries.

5 Must Know Facts For Your Next Test

1. 3-phenylbutanal is an α,β‑unsaturated aldehyde, meaning it has a carbon-carbon double bond adjacent to the carbonyl group.
2. The phenyl group at the third carbon position influences the reactivity and stability of 3-phenylbutanal in conjugate nucleophilic addition reactions.
3. Conjugate nucleophilic addition to 3-phenylbutanal involves the nucleophile attacking the β-carbon of the α,β‑unsaturated system, rather than the carbonyl carbon.
4. The resulting enolate ion intermediate formed during the conjugate addition can undergo further transformations, such as protonation or electrophilic addition.
5. 3-phenylbutanal is a valuable synthetic intermediate used in the production of fragrances, flavors, and other important organic compounds.

Review Questions

• Explain the reactivity of 3-phenylbutanal in conjugate nucleophilic addition reactions.
  • The presence of the α,β‑unsaturated aldehyde functionality in 3-phenylbutanal makes it susceptible to conjugate nucleophilic addition reactions. In these reactions, the nucleophile attacks the β-carbon of the α,β‑unsaturated system, rather than the carbonyl carbon. The phenyl group at the third carbon position can influence the stability and reactivity of the resulting enolate ion intermediate, which can then undergo further transformations.
• Describe how the structure of 3-phenylbutanal affects its applications in organic synthesis.
  • The combination of the aldehyde group and the phenyl substituent at the third carbon position gives 3-phenylbutanal unique reactivity and synthetic utility. The aldehyde functionality allows for further transformations, such as reduction to an alcohol or oxidation to a carboxylic acid. The phenyl group can also participate in various aromatic substitution reactions, providing access to a diverse range of organic compounds. As a result, 3-phenylbutanal is a valuable intermediate in the synthesis of fragrances, flavors, and other important organic molecules.
• Analyze the role of the enolate ion intermediate formed during conjugate nucleophilic addition to 3-phenylbutanal and its subsequent reactivity.
  • The conjugate nucleophilic addition to 3-phenylbutanal results in the formation of an enolate ion intermediate. This enolate ion is a nucleophilic species that can undergo further reactions, such as protonation to form a new carbonyl compound or electrophilic addition to introduce additional functionality. The stability and reactivity of the enolate ion can be influenced by the presence of the phenyl group at the third carbon position of 3-phenylbutanal. Understanding the behavior of this enolate intermediate is crucial for predicting and controlling the outcomes of reactions involving 3-phenylbutanal in organic synthesis.

Related terms

α,β‑Unsaturated Aldehydes: Aldehydes containing a carbon-carbon double bond adjacent to the carbonyl group, which gives rise to unique reactivity patterns.

Conjugate Nucleophilic Addition: A reaction where a nucleophile adds to the β-carbon of an α,β‑unsaturated carbonyl compound, rather than the carbonyl carbon.

Enolate Ion: A negatively charged intermediate formed during conjugate nucleophilic addition, which can then undergo further reactions.