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.

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