Introduces oxo carboxylic (keto) acids as molecules carrying both a carboxyl and a ketone group, then covers their naming rules and the major examples glyoxylic, pyruvic, acetoacetic and oxaloacetic acid with their IUPAC names. It explains keto-enol tautomerism and then the acidity, reactivity, hydrolysis, decarboxylation and oxidation of these acids. It closes with the Krebs cycle acids from citrate to oxaloacetate and a section on ketone bodies and their biological roles.
Topic 30 of 42 in the MU Sofia syllabus for Chemistry (Dental Medicine, Year 1). The free AceMed note covers it in 7 sections, about 1,175 words (8 min of reading), with 14 flashcards.
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Oxo carboxylic acids.
Structure and Nomenclature of Oxo Carboxylic Acids
Major examples: glyoxylic, pyruvic, acetoacetic and oxaloacetic acid. Keto-enol tautomerism.
Oxo carboxylic acids, also known as keto acids, are a type of organic compound that contain both a carboxylic acid group (-COOH) and a ketone group (-CO-). These compounds are particularly significant in biochemical processes, notably in the Krebs citric acid cycle (also known as the tricarboxylic acid cycle or TCA cycle).
Structure and Nomenclature of Oxo Carboxylic Acids
Structure:
Oxo carboxylic acids, also known as keto acids, are a type of carboxylic acid containing both a carboxyl group (COOH) and a ketone group (C=O) within the same molecule.
The key difference from a regular carboxylic acid is the presence of the separate ketone group, not directly attached to the carboxyl carbon.
Nomenclature:
Identifying the longest carbon chain containing the carboxyl group as the parent chain.
Numbering the carbon chain to give the carboxyl group the lowest possible number (usually C1).
Using the prefix "oxo-" to indicate the presence of a ketone group. The position of the ketone group is designated by the corresponding carbon number.
Replacing the "-e" ending of the parent alkane with "-oic acid" to signify the carboxylic acid functionality.
Examples:
Pyruvic acid (2-Oxopropanoic acid): This is a common alpha-keto acid with the ketone group on the second carbon (C2) of a three-carbon (propanoic) chain.
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