Chemistry · MU Sofia

11.3 Saturated dicarboxylic acids

Covers the general structure HOOC-(CH2)n-COOH of saturated dicarboxylic acids and their naming, then goes through oxalic, malonic, succinic, glutaric and adipic acids with their sources and uses. Also treats decarboxylation and cyclic anhydride formation, contrasts maleic and fumaric acids as unsaturated examples, and outlines the aromatic phthalic, isophthalic and terephthalic acids. A high-yield summary gives the acidity order of the saturated series and the cis/trans comparison of maleic and fumaric acid.

Inside: 15 sections · 5 labelled pictures · 11 flashcards · 5 min

Topic 28 of 42 in the MU Sofia syllabus for Chemistry (Dental Medicine, Year 1). The free AceMed note covers it in 14 sections, about 560 words (5 min of reading), with 11 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)

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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