Chemistry · MU Plovdiv

13. Saturated and unsaturated carboxylic acids – properties: oxalic acid, malonic acid, succinic acid, glutaric acid and adipic acid. Fumaric acid and maleic acid-isomerism and significance in metabolism.

Inside: 23 sections · 17 labelled pictures · 31 flashcards · 11 min

Topic 13 of 26 in the MU Plovdiv syllabus for Chemistry (Medicine, Year 1). The free AceMed note covers it in 21 sections, about 1,474 words (11 min of reading), with 31 flashcards.

In this note

  1. Saturated dicarboxylic acids. Structure and nomenclature.
  2. Representative saturated Dicarboxylic acids: oxalic, malonic, succinic, glutaric and adipic acids.
  3. Chemical properties.
  4. 1. Oxalic Acid:
  5. 2. Malic Acid:
  6. 3. Succinic Acid:
  7. 4. Glutamic Acid:
  8. 5. Adipic Acid:
  9. Decarboxylation and formation of cyclic anhydrides.
  10. Representative unsaturated dicarboxylic acids: maleic and fumaric acid.
  11. Aromatic dicarboxylic acids: phthalic, isophthalic and terephthalic acid.
  12. High Yield
  13. Acidity Trend of Saturated Dicarboxylic Acids
  14. Maleic vs Fumaric Acid (cis/trans isomers of HOOC–CH=CH–COOH)
  15. Unsaturated mono carboxylic acids.
  16. Representative unsaturated mono carboxylic acids: acrylic acid, methacrylic acid and oleic acid.
  17. Electrophilic addition of hydrogen bromide and polymerisation.
  18. Polyunsaturated fatty acids (PUFAs).
  19. Eicosanoids.
  20. Non-steroidal anti-inflammatory substances - aspirin, ibuprofen.
  21. Prostaglandin biosynthesis inhibition.

Saturated dicarboxylic acids. Structure and nomenclature.

  • Saturated dicarboxylic acids are organic compounds characterized by containing two carboxyl functional groups ($COOH$) in their structure. These compounds have the general formula HOOC-(CH2)_n-COOH, where $n$ represents the number of methylene ($CH2$) groups in the chain.
  • Structure:
  • The structure of a saturated dicarboxylic acid can be represented as follows:
  • HOOC-(CH2)n-COOH

1. Oxalic Acid:

  • Chemical Property: Oxalic acid (C2 H2 O4) is a dicarboxylic acid and is often used as a reducing agent in chemical reactions.
  • Source: Found in various vegetables such as spinach, tomatoes, and grapes.
  • Occurrence: Calcium oxalate, a salt of oxalic acid, is present in small amounts in urine and can contribute to the formation of urinary stones in the bladder and kidneys.

2. Malic Acid:

  • Chemical Property: Malic acid (C4 H5 O6) is a dicarboxylic acid and is often used as a food additive for its tart taste.
  • Source: Obtained by the oxidation of g-malic acid found in green parts of corn and sugar beet.

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