Propanone

Definition

Propanone, also known as acetone, is a simple ketone compound with the chemical formula CH$_3$COCH$_3$. It is a colorless, volatile, and flammable liquid that is widely used in various industrial and commercial applications. Propanone is particularly relevant in the context of the topics 19.1 Naming Aldehydes and Ketones and 19.7 Nucleophilic Addition of Hydride and Grignard Reagents: Alcohol Formation.

5 Must Know Facts For Your Next Test

1. Propanone is the simplest and most commonly encountered ketone, with a central carbonyl group flanked by two methyl groups.
2. In the context of 19.1 Naming Aldehydes and Ketones, propanone is named according to the IUPAC system, where the parent chain is identified as 'propane' and the carbonyl group is denoted by the suffix '-one'.
3. Propanone is a polar molecule due to the unequal sharing of electrons between the carbon and oxygen atoms in the carbonyl group.
4. In the context of 19.7 Nucleophilic Addition of Hydride and Grignard Reagents: Alcohol Formation, propanone can undergo nucleophilic addition reactions with hydride (H$^-$) or Grignard reagents to form secondary alcohols.
5. The nucleophilic addition of hydride to propanone produces 2-propanol (isopropanol), while the addition of a Grignard reagent produces a tertiary alcohol.

Review Questions

• Explain how the IUPAC naming system is used to name propanone.
  • According to the IUPAC naming system, propanone is named by identifying the parent chain as 'propane' and then adding the suffix '-one' to indicate the presence of a carbonyl (C=O) group. The name 'propanone' reflects the three-carbon parent chain and the ketone functional group. This systematic nomenclature allows for the unambiguous identification of the structure and properties of propanone within the broader class of ketone compounds.
• Describe the role of propanone in nucleophilic addition reactions involving hydride and Grignard reagents.
  • In the context of 19.7 Nucleophilic Addition of Hydride and Grignard Reagents: Alcohol Formation, propanone can undergo nucleophilic addition reactions. The nucleophilic addition of a hydride (H$^-$) ion to the carbonyl carbon of propanone produces 2-propanol (isopropanol), a secondary alcohol. Similarly, the addition of a Grignard reagent (R-Mg-X) to the carbonyl carbon of propanone results in the formation of a tertiary alcohol. These nucleophilic addition reactions are important in organic synthesis, as they allow for the selective reduction of the carbonyl group and the introduction of new functional groups.
• Analyze the relationship between the structure of propanone and its polarity, and explain how this property influences its reactivity and applications.
  • The structure of propanone, with a central carbonyl group flanked by two methyl groups, gives rise to its polarity. The unequal sharing of electrons between the carbon and oxygen atoms in the carbonyl group creates a partial positive charge on the carbon and a partial negative charge on the oxygen. This polarity allows propanone to participate in a variety of chemical reactions, including nucleophilic additions, as seen in the context of 19.7 Nucleophilic Addition of Hydride and Grignard Reagents: Alcohol Formation. Additionally, the polarity of propanone contributes to its widespread use as a solvent, paint remover, and in the production of various chemicals and pharmaceuticals, where its unique properties are leveraged for specific applications.

Related terms

Ketone: A class of organic compounds containing a carbonyl group (C=O) bonded to two alkyl or aryl groups.

Nucleophilic Addition: A type of organic reaction where a nucleophile adds to the carbon of a carbonyl group, forming a new bond and reducing the carbonyl.

Grignard Reagent: An organometallic compound with the general formula R-Mg-X, where R is an alkyl or aryl group and X is a halogen, used in organic synthesis to form new carbon-carbon bonds.