Organic Synthesis Experiments

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Written by J.A Dobado | Last Updated on May 2, 2024

Organic Synthesis Experiments
Image taken by Angel Sánchez

In this section, we describe a series of practices related to the reactivity of functional groups that are usually studied in an experimental course of Organic Chemistry.

Most of the experiments described correspond to one-step transformations. In addition, others deal with the multistep synthesis of a compound and the study of the concept of protective group within a synthetic route.

For this reason, in some cases a difunctional compound is also used. In this way, it will be used to develop the concept of chemoselectivity against different reagents but of the same family.

Experiment selection

The experiments have been chosen in order to have as wide a range of substrates as possible. Aliphatic or aromatic substrates have been selected, as well as different types of reagents. Also, various types of reactions have been taken into account: for example, substitution, elimination, addition, oxidation-reduction, etc. and reaction conditions (reflux, room temperature, cold, etc.). For this reason, the use of different methods of isolation and purification of organic compounds is also encouraged.

Likewise, the choice of the practicals has the ultimate goal of including the main basic laboratory operations in experiments of low or medium complexity, either as a whole or by choosing a few of them.

Accordingly, a selection of Organic Synthesis Experiments is listed below:

  1. Polystyrene production by radical polymerization
  2. Preparation of a synthetic detergent
  3. Obtaining biodiesel from vegetable oil
  4. Synthesis of aspirin
  5. Preparation of β-naphthyl methyl ether
  6. Preparation of 2-butoxynaphthalene
  7. Oxidation of 4-chlorobenzyl alcohol to 4-chlorobenzoic acid
  8. Claisen-Schmidt reaction: α,β-unsaturated ketones
  9. Benzaldehyde disproportionation (Cannizzaro reaction)
  10. Oxidation of cyclohexene to yield adipic acid
  11. Methyl benzoate nitration
  12. Synthesis of cinnamic acid
  13. Chemoselective reductions of 4-nitroacetophenone
  14. p-Nitroaniline synthesis
  15. Methyl benzoate nitration
  16. Synthesis of methyl orange
  17. Paracetamol synthesis
  18. Oxidation of acetophenone with sodium hypochlorite (haloform reaction)
  19. Synthesis of benzoic acid from Grignard reagent (phenylmagnesium bromide)
  20. Obtaining t-butyl chloride: use in the synthesis of 1,4-di-t-butylbenzene
  21. Obtaining phenolphthalein
  22. Acetanilide synthesis
  23. Dehydration of cyclohexanol to give cyclohexene
  24. Synthesis of Martius yellow dye
  25. Creatine synthesis (sports dietary supplement)
  26. Preparation of N-(p-chlorophenyl)-maleimide
  27. Chiral resolution of (±)-α-methylbenzylamine
  28. Oxidative coupling of alkynes (Glaser-Eglinton-Hay)
  29. Synthesis of acetylferrocene
  30. Reduction of cinnamaldehyde with LiAlH4
  31. Preparation of calix[4]pyrrole
  32. Conversion of citral to α- and β-ionone
  33. Reaction of cyclohexene with oxone
  34. Preparation of dibenzylamine hydrochloride
  35. Preparation of benzyl butyl ether
  36. Synthesis of γ-tert-butyl-ε-caprolactone from oxidation of 4-tert-butylcyclohexanone
  37. Synthesis of chiral ethyl 3-hydroxybutanoate
  38. Preparation of p-cymene from limonene
  39. Synthesis of racemic 1,1′-bi-2-naphthol
  40. Reaction of 4-nitrobenzaldehyde and dimedone
  41. Synthesis of 7-hydroxy-3-carboxycoumarin
  42. Synthesis of laurolactam from cyclododecanone
  43. Preparation of soap from vegetable oil
  44. Synthesis of nylon 6,6
  45. Preparation of 7,7-dichlorobicyclo[4.1.0]heptane
  46. Bromination of α-methylstyrene
  47. Synthesis of pinacol and pinacolone
  48. Production of adipic acid with H2O2/Na2WO4
  49. Bromine addition to cyclohexene
  50. Graphite-catalysed reaction of xylene with 2-bromopropane
  51. Obtaining ortho-nitrophenol
  52. Reaction of benzaldehyde with oxone
  53. Preparation of 5,5-bis(hydroxymethyl)-2-phenyl-1,3-dioxane in water
  54. Reaction of cyclohexanone with NaBH4
  55. Solvent-free Wittig reaction
  56. Reaction of 9-anthracenemethanol with N-methylmaleimide (Diels-Alder reaction in water)
  57. Obtaining phthalates from recycled polymers (PET)
  58. Producing slime (cross-linked biodegradable polymers)
  59. Polymers from starch
  60. Synthesis of tetrahydropyrimidinone (Biginelli reaction)
  61. Multi-component reaction in water (Passerini reaction)
  62. Preparation of meso-diethyl-2,2′-dipyrromethane in water
  63. Preparation of 1-butyl-3-methylimidazolium derivative (ionic liquid)
  64. Photochemical [2+2] cycloaddition of cinnamic acid to obtain truxillic acid
  65. Synthesis of 3‐methylcyclohex‐2‐enone
  66. Synthesis of (R)‐warfarin
  67. Synthesis of copper phthalocyanine
  68. Photochromic dimer from 2,4,5-triphenylimidazole
  69. Reduction of benzophenone into diphenylmethanol with NaBH4
  70. Acetophenone oxime preparation

Microscale Experiments

  1. Synthesis of 2-bromohexane
  2. Partial hydrogenation of a vegetable oil with cyclohexene and Pd(C) (margarine production)
  3. Isomerization of maleic acid (cis) to fumaric acid (trans)
  4. Ethyl iodide from ethanol
  5. Preparation of 4-methyl-3- and 4-methyl-2-nitroacetanilide from 4-methylaniline
  6. Synthesis of 2-iodobenzoic acid (Sandmeyer reaction)
  7. Compounds for the fragrance industry (ester synthesis)
  8. Preparation of 9-bromoanthracene
  9. KMnO4 oxidation of alkylbenzenes
  10. Synthesis of anthrone from anthraquinone
  11. Wintergreen oil from aspirin tablets
  12. Vanillin transformations
  13. Synthesis of 2,5-dimethyl-1-phenylpyrrole by Paal-Knorr reaction

References

  • Isac-García, J.; Dobado, J. A.; Calvo-Flores, F. G.; and Martínez-García, H. (2015). Experimental Organic Chemistry Laboratory Manual. Elsevier Science & Technology. ISBN: 978-0-12-803893-2
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