Carboxylate Ion

Definition

The carboxylate ion is a negatively charged species formed when a carboxylic acid loses a proton (H+). It is a key intermediate in various organic chemistry reactions and plays a crucial role in understanding the structure and properties of carboxylic acids, as well as their reactions and the chemistry of acid anhydrides.

5 Must Know Facts For Your Next Test

1. The carboxylate ion is a resonance-stabilized species, with the negative charge delocalized between the two oxygen atoms.
2. In the oxidation of aldehydes and ketones, the carboxylate ion is an important intermediate that is formed during the final step of the reaction.
3. Carboxylic acids can be converted to their corresponding carboxylate ions through the removal of a proton, which increases the solubility and reactivity of the compound.
4. Carboxylate ions are important nucleophiles in many organic reactions, such as the formation of esters and amides from carboxylic acids.
5. Acid anhydrides can undergo hydrolysis to form carboxylate ions, which can then participate in further reactions.

Review Questions

• Explain the role of the carboxylate ion in the drawing of resonance forms for organic compounds.
  • The carboxylate ion is a resonance-stabilized species, where the negative charge is delocalized between the two oxygen atoms. This delocalization of the charge results in increased stability, which is an important consideration when drawing resonance forms of organic compounds containing carboxylic acid or carboxylate functional groups. The ability to draw multiple resonance structures for the carboxylate ion helps to understand the reactivity and properties of these compounds.
• Describe the significance of the carboxylate ion in the oxidation of aldehydes and ketones.
  • In the oxidation of aldehydes and ketones, the carboxylate ion is an important intermediate that is formed during the final step of the reaction. The carboxylate ion is generated when the aldehyde or ketone is oxidized to a carboxylic acid, and the proton is subsequently removed. This carboxylate ion is a key species that can then participate in further reactions, such as the formation of esters or amides, and is essential for understanding the overall mechanism and products of the oxidation of aldehydes and ketones.
• Analyze the role of the carboxylate ion in the structure and properties of carboxylic acids, as well as their reactions and the chemistry of acid anhydrides.
  • The carboxylate ion is central to understanding the structure and properties of carboxylic acids, as well as their reactivity and the chemistry of acid anhydrides. When a carboxylic acid loses a proton, it forms the carboxylate ion, which has increased solubility and reactivity compared to the parent acid. The carboxylate ion can participate in various organic reactions, such as the formation of esters and amides, and is also an important intermediate in the hydrolysis of acid anhydrides to form carboxylic acids. Additionally, the resonance stabilization of the carboxylate ion influences the acidity and reactivity of carboxylic acids, making it a crucial concept in understanding the behavior of these compounds in organic chemistry.

Related terms

Carboxylic Acid: An organic compound containing a carboxyl group (-COOH), which consists of a carbonyl group (C=O) and a hydroxyl group (-OH).

Resonance: The ability of a molecule or ion to exist in multiple equivalent structures, where the electrons are delocalized, resulting in increased stability.

Nucleophile: A species that donates a pair of electrons to form a new covalent bond, often attacking electrophilic centers.