A review of aqueous organic reactions for the undergraduate teaching laboratory

Figures & data

short-legendScheme 1. Wittig synthesis of 4-vinylbenzoic acid 12.

short-legendScheme 2. Horner–Wadsworth–Emmons preparation of a sunscreen analog 13.

short-legendScheme 3. Alkene syntheses via Knoevenagel condensations 17.

short-legendScheme 4. Coumarin generation via one-pot consecutive reactions 18.

short-legendScheme 5. Hantzsch synthesis of diludine 19.

short-legendScheme 6. Aldol reaction between 2-acetylpyridine and 4-nitrobenzaldehyde at 50C 24.

short-legendScheme 7. Aldol reaction between 2-acetylpyridine and 4-nitrobenzaldehyde at room temperature 24.

short-legendScheme 8. Alcohol preparation by a Grignard-like reaction 27.

short-legendScheme 9. Conversion of an aziridine to an oxazolidinone using carbon dioxide 29.

short-legendScheme 10. Pd/C-catalyzed Suzuki synthesis of an NSAID analog 37.

short-legendScheme 11. Heck synthesis of trans-4-acetylcinnamic acid 41.

short-legendScheme 12. Sonogashira coupling using catalytic Pd(OAc)2 43.

short-legendScheme 13. ROMP of exo-7-oxabicyclo[2.2.l]hept-5-ene-2,3-dicarboxylic anhydride 49.

short-legendScheme 14. “Click” synthesis of 1,2,3-triazole derivatives 51.

short-legendScheme 15. Diels–Alder reaction between anthracene-9-methanol and N-methylmaleimide 52.

short-legendScheme 16. Hetero Diels–Alder preparation of lactones 53.

short-legendScheme 17. Hetero Diels–Alder synthesis of N-benzyl-2-azanorbornene 54.

short-legendScheme 18. Diapocyanin synthesis via aryl radical coupling 55.

short-legendScheme 19. Synthesis of racemic 1,1′-bi-2-naphthol 58.

short-legendScheme 20. Aromatic substitution reaction between pyrrole and 3-pentanone 60.

short-legendScheme 21. Aromatic nitration of tyrosine 62.

short-legendScheme 22. Hydrogen peroxide-mediated epoxidation of geraniol 63.

short-legendScheme 23. Preparation of cyclohexene oxide using Oxone 65.

short-legendScheme 24. Oxidation of benzaldehyde to benzoic acid 66.

short-legendScheme 25. Phase-transfer catalytic synthesis of adipic acid 68.

short-legendScheme 26. Conversion of secondary alcohols to ketones with hydrogen peroxide 69.

short-legendScheme 27. Cyclohexanone reduction using sodium borohydride 71.

short-legendScheme 28. Synthesis of 2-ethoxy-4-(hydroxymethyl) phenol 73.

short-legendScheme 29. Enzymatic reduction of ethyl acetoacetate 75, 76.

short-legendScheme 30. Bromohydrin formation from 3-sulfolene 78.

short-legendScheme 31. Synthesis of an iodolactone from 4-pentenoic acid 79.

short-legendScheme 32. An etherification reaction under phase-transfer catalysis 80.

short-legendScheme 33. Conversion of benzaldehyde into a cyclic acetal 82.

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