Organic Chemistry with Laboratory

Lectures: 8 h 

Laboratory: 6 h

Main Topics:

  • Perfumes, fragrances and aromas: description and applications. Classification of aromas.
  • Interactions with olfactory receptors: relationship between organic molecules’ features (e.g., chain length in some alcohols) and olfactory response.
  • Use of organic synthesis to obtain: i) organic molecules with specific odorous properties; ii) hard-to-find odorous substances; iii) new varieties of perfumes.
  • Extraction of fragrances from plants or animals: availability issues, extracted amounts and cost-related issues. “Non-natural” fragrances obtained via synthetic routes (example of calone: sea breeze).
  • Synthesis design of organic molecules: functional groups; structural characteristics; three-dimensional structure; stereochemistry; volatility; polarity; reactivity.
  • Relationship between odorous properties and (a) functional groups; (b) structure; (c) isomerism; (d) lock-and-key model.
  • Preparation of “nature-identical” organic compounds.
  • Examples of synthesis and spectroscopic characterization (IR, NMR and mass spectra) of: coumarin; vanillin; ionones; aldehyde derivatives (e.g., lilac adehydes and olfactory characteristics); synthetic musks: nitro musks; polycyclic musks; macrocyclic musks; alicyclic musks.
  • Synthesis and biosynthesis of irones. Development and optimization of a reaction. Synthesis of enantiopure irones and enzymatic resolution.
  • Terpenes and perfumes.
  • Iso and Super
  • Organic Chemistry Laboratory: I) Preparation of esters with aromatic notes: description of the different synthetic steps, final processing, extraction, purification by distillation. Purity check by proton NMR. II) Synthesis of molecules with odorous properties from natural substrates. Thin layer chromatography (TLC): separation conditions optimization. Purification by column chromatography: procedure description. Proton NMR of the purified product.

Lecturers:
    Prof. Antonella Capperucci, Dr. Damiano Tanini
    Department of Chemistry “Ugo Schiff”
    University of Florence, Italy
    email: antonella.capperucci (at) unifi.it | damiano.tanini (at) unifi.it
    phone: + 39 055 4573550