Organic Synthesis Experiments

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 (Organic Synthesis).

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.

Image taken by Angel Sánchez Angel Sanchez

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 practices 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. Oxidation of 4-chlorobenzyl alcohol to 4-chlorobenzoic acid
  7. Claisen-Schmidt reaction: α,β-unsaturated ketones
  8. Cannizzaro reaction
  9. Oxidation of cyclohexene to yield adipic acid
  10. Methyl benzoate nitration
  11. Synthesis of cinnamic acid
  12. Chemoselective reductions of 4-nitroacetophenone
  13. p-Nitroaniline synthesis
  14. Methyl benzoate nitration
  15. Synthesis of methyl orange
  16. Paracetamol synthesis
  17. Oxidation of acetophenone with sodium hypochlorite (haloform reaction)
  18. Synthesis of benzoic acid from Grignard reagent (phenylmagnesium bromide)
  19. Obtaining t-butyl chloride: use in the synthesis of 1,4-di-t-butylbenzene.
  20. Obtaining phenolphthalein
  21. Synthesis of acetanilide
  22. Isomerization of maleic acid (cis) to fumaric acid (trans)
  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. Acetylferrocene synthesis
  30. Reduction of cinnamaldehyde with LiAlH4
  31. Preparation of calix[4]pyrrole
  32. Conversion of citral to α- and β-ionone.
  33. Synthesis of 2-bromohexane
  34. Partial hydrogenation of a vegetable oil with cyclohexene and Pd(C) (margarine production)
  35. Ethyl iodide from ethanol
  36. Preparation of 4-methyl-3- and 4-methyl-2-nitroacetanilide from 4-methylaniline
  37. Synthesis of 2-iodobenzoic acid (Sandmeyer reaction)
  38. Preparation of 9-bromoanthracene
  39. Oxidation of alkylbenzenes with KMnO4
  40. Synthesis of anthrone from anthraquinone
  41. Oil of wintergreen from aspirin tablets
  42. Vanillin transformations
  43. Synthesis of 2,5-dimethyl-1-phenylpyrrole by Paal-Knorr reaction
  44. Reaction of cyclohexene with oxone
  45. Dibenzylamine hydrochloride preparation
  46. Preparation of benzyl butyl ether
  47. 4-tert-Butylcyclohexanone oxidation
  48. Synthesis of chiral ethyl 3-hydroxybutanoate
  49. Preparation of p-cymene from limonene
  50. Synthesis of racemic 1,1′-bi-2-naphthol
  51. 4-Nitrobenzaldehyde and dimedone reaction
  52. Synthesis of 7-hydroxy-3-carboxicoumarin
  53. Synthesis of laurolactam from cyclododecanone
  54. Preparation of soap from vegetable oil
  55. Synthesis of nylon 6,6
  56. Preparation of 7,7-dichlorobicyclo[4.1.0]heptane
  57. Bromination of α-methylstyrene
  58. Pinacol and pinacolone synthesis
  59. Compounds for the fragrance industry (ester synthesis)
  60. Production of adipic acid with H2O2/Na2WO4
  61. Bromine addition to cyclohexene
  62. Graphite-catalyzed reaction of xylene with 2-bromopropane
  63. Obtaining ortho-nitrophenol
  64. Reaction of benzaldehyde with oxone
  65. Preparation of 5,5-bis(hydroxymethyl)-2-phenyl-1,3-dioxane
  66. Reaction of cyclohexanone with NaBH4
  67. Suzuki reaction of C-C bond formation
  68. Wittig reaction in the absence of solvent
  69. Reaction of 9-anthracenemethanol with N-methylmaleimide
  70. Phthalates from recycled polymers (PET)
  71. Production of cross-linked biodegradable polymers
  72. Starch-based polymers
  73. Synthesis of tetrahydro-pyrimidinone
  74. Passerini reaction
  75. Preparation of meso-diethyl-2,2′-dipyrromethane
  76. Preparation of 1-butyl-3-methylimidazolium derivative
  77. Preparation of 7-hydroxy-4-methyl-2H-chromen-2-one
  78. [2+2] cycloaddition of cinnamic acid