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pKa phenol = 9.9 pKa2 of carbonic acid = 10.33 PowerPoint Presentation
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  1. Chandrasekhar, S.; Basu, Debjit; Sailu, M.; Kotamraju, S. Novel synthetic route to the tricyclic core of ()-galanthamine. Tetrahedron Letters (2009), 50(34), 4882-4884.

  2. pKa phenol = 9.9 pKa2 of carbonic acid = 10.33

  3. The ClaisenRearrangment is a [3,3] sigmatropic rearrangement Aromatic Claisen Rearrangement Cope Rearrangement is related

  4. Sigmatropic: One sigma bond is changed to another.

  5. pKa conjugate acid of imidazole = 7.2

  6. DIPEA = Diisopropylethylamine (Hunig’s Base). This base is more sterically hindered, and thus less nucleophilic, than triethylamine. pKa of the conjugate acid of Hunig’s base = 11.0 MOM = Methoxymethyl MOMCl = H3C-O-CH2-Cl

  7. 2,6-Lutidine = pKa conjugate acid of 2,6-lutidine = 6.7

  8. pKa hydroxylamine hydrochloride = 6 pKa conjugate acid of pyridine = 5.2 pKa conjugate acid of triethylamine = 10.6

  9. pKaacetonitrile = 25 pKaphenylacetonitrile = 22 DMPU = Dimethylpropyleneurea = solvent to replace HMPA, a carcinogen LDA = lithium diisopropylamide pKa of diisopropylamine(conjugate acid of LDA) = 36

  10. pKa p-toluenesulfonic acid = - 0.4

  11. DPPA = diphenylphosphorylazide = DBU = Diazabicycloundecene = Conjugate acid of DBU pKa = 13.2