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. Preparation of 2-butoxynaphthalene
    7. Oxidation of 4-chlorobenzyl alcohol to 4-chlorobenzoic acid
    8. Claisen-Schmidt reaction: α,β-unsaturated ketones
    9. 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. Synthesis of acetanilide
    23. Isomerization of maleic acid (cis) to fumaric acid (trans)
    24. Dehydration of cyclohexanol to give cyclohexene
    25. Synthesis of Martius yellow dye
    26. Creatine synthesis (sports dietary supplement)
    27. Preparation of N-(p-chlorophenyl)-maleimide
    28. Chiral resolution of (±)-α-methylbenzylamine
    29. Oxidative coupling of alkynes (Glaser-Eglinton-Hay)
    30. Acetylferrocene synthesis
    31. Reduction of cinnamaldehyde with LiAlH4
    32. Preparation of calix[4]pyrrole
    33. Conversion of citral to α- and β-ionone.
    34. Synthesis of 2-bromohexane
    35. Partial hydrogenation of a vegetable oil with cyclohexene and Pd(C) (margarine production)
    36. Ethyl iodide from ethanol
    37. Preparation of 4-methyl-3- and 4-methyl-2-nitroacetanilide from 4-methylaniline
    38. Synthesis of 2-iodobenzoic acid (Sandmeyer reaction)
    39. Preparation of 9-bromoanthracene
    40. Oxidation of alkylbenzenes with KMnO4
    41. Synthesis of anthrone from anthraquinone
    42. Oil of wintergreen from aspirin tablets
    43. Vanillin transformations
    44. Synthesis of 2,5-dimethyl-1-phenylpyrrole by Paal-Knorr reaction
    45. Reaction of cyclohexene with oxone
    46. Dibenzylamine hydrochloride preparation
    47. Preparation of benzyl butyl ether
    48. 4-tert-Butylcyclohexanone oxidation
    49. Synthesis of chiral ethyl 3-hydroxybutanoate
    50. Preparation of p-cymene from limonene
    51. Synthesis of racemic 1,1′-bi-2-naphthol
    52. 4-Nitrobenzaldehyde and dimedone reaction
    53. Synthesis of 7-hydroxy-3-carboxicoumarin
    54. Synthesis of laurolactam from cyclododecanone
    55. Preparation of soap from vegetable oil
    56. Synthesis of nylon 6,6
    57. Preparation of 7,7-dichlorobicyclo[4.1.0]heptane
    58. Bromination of α-methylstyrene
    59. Pinacol and pinacolone synthesis
    60. Compounds for the fragrance industry (ester synthesis)
    61. Production of adipic acid with H2O2/Na2WO4
    62. Bromine addition to cyclohexene
    63. Graphite-catalyzed reaction of xylene with 2-bromopropane
    64. Obtaining ortho-nitrophenol
    65. Reaction of benzaldehyde with oxone
    66. Preparation of 5,5-bis(hydroxymethyl)-2-phenyl-1,3-dioxane
    67. Reaction of cyclohexanone with NaBH4
    68. Suzuki reaction of C-C bond formation
    69. Wittig reaction in the absence of solvent
    70. Reaction of 9-anthracenemethanol with N-methylmaleimide
    71. Phthalates from recycled polymers (PET)
    72. Production of cross-linked biodegradable polymers
    73. Starch-based polymers
    74. Synthesis of tetrahydro-pyrimidinone
    75. Passerini reaction
    76. Preparation of meso-diethyl-2,2′-dipyrromethane
    77. Preparation of 1-butyl-3-methylimidazolium derivative
    78. Preparation of 7-hydroxy-4-methyl-2H-chromen-2-one
    79. [2+2] cycloaddition of cinnamic acid