Chemistry · MU Sofia

11.1 Mono carboxylic acids

Introduces carboxylic acids through the carboxyl group, its planar sp² structure and IUPAC naming with common names such as formic acid. Goes on to explain how resonance stabilises the carboxylate ion and so governs acidity, then lists chemical properties and esterification, saponification, Claisen condensation and amide hydrolysis. Ends with physical properties, substituent effects on acidity and the Hell–Volhard–Zelinsky reaction, and includes paracetamol and lidocaine as amide drugs.

Inside: 13 sections · 12 labelled pictures · 15 flashcards · 9 min

Topic 26 of 42 in the MU Sofia syllabus for Chemistry (Dental Medicine, Year 1). The free AceMed note covers it in 13 sections, about 1,179 words (9 min of reading), with 15 flashcards.

In this note

  1. Mono carboxylic acids.
  2. Saturated and aromatic carboxylic acids.
  3. Relationship between structure and acidity.
  4. Chemical properties
  5. Nucleophilic acyl substitution reactions (AN + DN): esterification and anhydrides formation
  6. Alkaline hydrolysis (saponification) of esters and Claisen condensation, Reaction of esters with amines Esterification.
  7. Relationship to ribosomal protein synthesis.
  8. Acid hydrolysis of amides.
  9. Amides as drugs: paracetamol and lidocaine.
  10. High Yield
  11. Physical Properties of Carboxylic Acids
  12. Effect of Substituents on Acidity
  13. Hell–Volhard–Zelinsky (HVZ) Reaction

Mono carboxylic acids.

  • 1. Definition:
  • Carboxylic acids are compounds that contain the carboxyl group.
  • 2. Composition of Carboxyl Group:
  • The carboxyl functional group consists of two functional groups: a carbonyl group bonded to a hydroxyl group.
  • 3. Chemical Formula:
  • The carboxyl group is often represented in condensed form as –COOH.

Structure and nomenclature.

  • Carboxylic Acid Structure:
  • Carboxylic acids, found in substances like pepper and cinnamon, possess a planar structure due to sp² hybridization.
  • This planarity arises from the arrangement of the carbon atom in the carboxyl group, which is sp²-hybridized, enabling the formation of a double bond with one oxygen atom and a single bond with another oxygen atom.
  • The presence of the carboxyl group (-COOH) imparts acidic nature to carboxylic acids, allowing them to readily release a proton (H⁺).
  • In the chemical formula R-C-OH, where R represents an alkyl or aryl group, the carboxyl carbon is bonded to both an oxygen atom (via a double bond) and a hydroxyl group (-OH), forming the characteristic carboxyl functional group.
  • Nomenclature of Carboxylic Acids:
  • In the IUPAC system of nomenclature, the carboxyl carbon is designated as #1, and other substituents are located and named accordingly.
  • The longest chain carrying the carboxyl group is considered the parent structure and is named by replacing the -e of the corresponding hydrocarbon with the suffix "oic acid".
  • The aliphatic carboxylic acids have common names derived from their sources rather than their chemical structures.
  • Examples include:
  • Formic acid: Derived from "formica," Latin for ant, due to its presence in ant venom.

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