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  • 1 pages Organic Lab Answer 35
    • Organic Lab Answer 35
    • University of Florida
    • Organic Chemistry 2 Lab
    • CHM 2212 - Fall 2010
    • 35 Kirmse, W. Angew. Chem. Int. Ed. 2004, 43, 1767 Herzberg, G.; Shoosmith, J. Nature 1959, 183, 1801 Herzberg, G. Proc. Roy. Soc. London 1961, 262A, 291 Mackay, C.; Wolfgang, R. J. Am. Chem. Soc. 1961, 83, 2399 Gutsche, C.D.; Bachman, G.L.; Coffey, R.S.
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    Organic Lab Answer 35

  • 1 pages Organic Lab Answer 28
    • Organic Lab Answer 28
    • University of Florida
    • Organic Chemistry 2 Lab
    • CHM 2212 - Fall 2010
    • 28 + NMe3 Ar _ _ + NMe3 + H2O Ar + H 3 O+ + NMe3 Ar Ar + NMe3 Ar = p-NO2 -C6 H4 Hughes, E.D.; Ingold, C.K. J. Chem. Soc. 1933, 523 Hughes, E.D.; Ingold, C.K.; Patel, C.S. J. Chem. Soc. 1933, 526 Carbenes or methylenes (general) Reviews: Huisgen, R. Angew.
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    Organic Lab Answer 28

  • 1 pages Organic Lab Answer 127
    • Organic Lab Answer 127
    • University of Florida
    • Organic Chemistry 2 Lab
    • CHM 2212 - Fall 2010
    • 127 Phenyl Cation (phenylium ion, arylium ion, benzene cation) + R Reviews: Ambroz, H.B.; Kemp, T.J. Chem. Soc. Rev. 1979, 8, 353 N2 + X R - + - N2 + X- X R R Sandmeyer, T., Chem. Ber . 1884, 17, 1633 Sandmeyer, T., Chem. Ber . 1884, 17, 2650 Lewis, E.S.
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    Organic Lab Answer 127

  • 1 pages Organic Lab Answer 225
    • Organic Lab Answer 225
    • University of Florida
    • Organic Chemistry 2 Lab
    • CHM 2212 - Fall 2010
    • 225 Webster, O.W.; Mahler, W.; Benson, R.E. J. Org. Chem. 1960, 25, 1470 Webster, O.W.; Mahler, W.; Benson, R.E. J. Am. Chem. Soc. 1962, 84, 3678 Phillips, W.D.; Rowell, J.C.; Weissman, S.I. J. Chem. Phys. 1960, 33, 626 (ESR spectrum) NC CN NC . _ CN Acke
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    Organic Lab Answer 225

  • 1 pages Organic Lab Answer 27
    • Organic Lab Answer 27
    • University of Florida
    • Organic Chemistry 2 Lab
    • CHM 2212 - Fall 2010
    • 27 Mitchell, A.D.; Thorpe, J.F. Proc. Chem. Soc. 1911, 26, 248 Mitchell, A.D.; Thorpe, J.F. Proc. Chem. Soc. 1911, 26, 2261 Dieckmann, W. Chem. Ber. 1911, 44, 981 Busch, M.; Limpach, O. Chem. Ber. 1911, 44, 1573 Locquin, R. Compt. Rend. 1911, 153, 284 Cur
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    Organic Lab Answer 27

  • 1 pages Organic Lab Answer 126
    • Organic Lab Answer 126
    • University of Florida
    • Organic Chemistry 2 Lab
    • CHM 2212 - Fall 2010
    • 126 Balaban, A.T.; Nenitzescu, C.D. J. Chem. Soc. 1961, 3553; 3561; 3564 Praill, P.F.G.; Whitear, A.L. J. Chem. Soc. 1961, 3573 Praill, P.F.G.; Whitear, A.L. Proc. Chem. Soc. 1961, 312 Phenonium Ions + + + R1 R2 + R4 R1 R4 R1 R4 R1 R4 R1 + R3 R2 R3 R2 R3
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    Organic Lab Answer 126

  • 1 pages Organic Lab Answer 224
    • Organic Lab Answer 224
    • University of Florida
    • Organic Chemistry 2 Lab
    • CHM 2212 - Fall 2010
    • 224 Rathore, R.; Kochi, J.K. Adv. Phys. Org. Chem. 1998, 31, 193 Webster, O.W. J. Polym. Sci. A 2002, 40, 210 (tetracyanoethylene radical anion) Todres, Z.V. Organic Ion Radicals, Marcel Dekker, Inc.: New York, 2003 _ K K K+ . Berthelot, M. Compt. Rend. 1
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    Organic Lab Answer 224

  • 1 pages Organic Lab Answer 26
    • Organic Lab Answer 26
    • University of Florida
    • Organic Chemistry 2 Lab
    • CHM 2212 - Fall 2010
    • 26 Harder, S. Chem. Eur. J. 2002, 8, 3229 Buncel, E.; Dust, J.M. Carbanion Chemistry: structures and mechanisms, Oxford University Press: Oxford, 2003 stabilities of carbanions: Breslow, R.; Balasubramanian, K. J. Am. Chem. Soc. 1969, 91, 5182 (thermodyna
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    Organic Lab Answer 26

  • 1 pages Organic Lab Answer 125
    • Organic Lab Answer 125
    • University of Florida
    • Organic Chemistry 2 Lab
    • CHM 2212 - Fall 2010
    • 125 Reviews: Balaban, A.T.; Schroth, W.; Fischer, G.W. Adv. Heterocyclic Chem. 1969, 10, 241 Balaban, A.T. Studies in Org. Chem. 1979, 3, 79 O O 2 O COOEt O+ O H3 O+ HX X- - CO2 O OH O O X = Cl, Br, I, PtCl6 , NO 3 , oxalate, tartrate, picrate, salicylate
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    Organic Lab Answer 125

  • 1 pages Organic Lab Answer 223
    • Organic Lab Answer 223
    • University of Florida
    • Organic Chemistry 2 Lab
    • CHM 2212 - Fall 2010
    • 223 Ph-Se-Se-Ph Ph-Se . 2 Ph-Se +R . PhSe COOMe PhSe . COOMe R PhSe COOMe PhSe R . COOMe SePh Ph-Se-Se-Ph - Ph-Se . R SePh R COOMe Back, T.G.; Krishna, M.V. J. Org. Chem. 1988, 53, 2533 (ii) Selanyl R Se . Reviews: None. Ph3 Se-X X-irradiation . Ph2 Se-X
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    Organic Lab Answer 223

  • 1 pages Organic Lab Answer 25
    • Organic Lab Answer 25
    • University of Florida
    • Organic Chemistry 2 Lab
    • CHM 2212 - Fall 2010
    • 25 Rule, M.; Matlin, A.R.; Dougherty, D.A.; Hilinski, E.; Berson, J.A. J. Am. Chem. Soc. 1979, 101, 5098 *3 O O O h CH2 =CH 2 . O Freilich, S.F.; Peters, K.S. J. Am. Chem. Soc. 1981, 103, 6255; 1985, 107, 3819 (evidence for biradical in Paterno-Bchi react
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    Organic Lab Answer 25

  • 1 pages Organic Lab Answer 124
    • Organic Lab Answer 124
    • University of Florida
    • Organic Chemistry 2 Lab
    • CHM 2212 - Fall 2010
    • 124 BF4 - O+ Me2 O + BF3 + Et-F Et OO2N NO2 Et3 O+ NO2 Meerwein, H.; Hinz, G.; Hofmann, P.; Kronig, E.; Pfeil, E. J. Prakt. Chem. 1937, 147, 257 RO O OMCl n-1 + 2 R-O-R.MCln + R3 O+ MCln+1 Meerwein, H.; Battenberg, E.; Gold, H.; Pfeil, E.; Willfang, G. J.
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    Organic Lab Answer 124

  • 1 pages Organic Lab Answer 222
    • Organic Lab Answer 222
    • University of Florida
    • Organic Chemistry 2 Lab
    • CHM 2212 - Fall 2010
    • 222 (i) Phenylselanyl (phenylseleno) radical Se . Reviews: None. Schmidt, U.; Mller, A.; Markau, K. Tetrahedron Lett. 1963, 1091 (ESR) Se Ph Ph h 2 PhCH 2 Se Se Se Ph h Ph Se 2 Ph-Se . . Schmidt, U.; Mller, A.; Markau, K. Chem. Ber. 1964, 97, 405 Ph-Se-Se
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    Organic Lab Answer 222

  • 1 pages Organic Lab Answer 24
    • Organic Lab Answer 24
    • University of Florida
    • Organic Chemistry 2 Lab
    • CHM 2212 - Fall 2010
    • 24 h N N - N2 . . h - CO O Dowd, P. J. Am. Chem. Soc. 1966, 88, 2587 (first observation of biradicals by ESR) R3 R1 R1 . OR R3 ROH R2 R2 . R4 R1 R3 R2 R4 R4 Bergman, R.G.; Jones, R.R., J. Am. Chem. Soc. 1972, 94, 660 (Bergmann cyclization) CH2 . CH2 Pagni
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    Organic Lab Answer 24

  • 1 pages Organic Lab Answer 123
    • Organic Lab Answer 123
    • University of Florida
    • Organic Chemistry 2 Lab
    • CHM 2212 - Fall 2010
    • 123 R1 OH R1 R2 H H pelargonin H OH cyanidin OH OH delphinidin OMe OMe enidin (malvidin, syringidin) + HO O - Cl R2 Name OH OH Pratt, D.D.; Robinson, R.; Williams, P.N. J. Chem. Soc. 1924, 125, 199 Robertson, A.; Robinson, R. J. Chem. Soc. 1926, 1713 Robe
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    Organic Lab Answer 123

  • 1 pages Organic Lab Answer 221
    • Organic Lab Answer 221
    • University of Florida
    • Organic Chemistry 2 Lab
    • CHM 2212 - Fall 2010
    • 221 N S S N h 2 N S . Maillard, B.; Ingold, K.U. J. Am. Chem. Soc. 1976, 98, 520 (vi) Thiophenoxy (phenylthio, phenylthiyl, benzenethiyl) radicals . S R Reviews: None. X S S h S . 2 X X X = H, MeO, Me2 N, OH, EtOOC, Ph Schmidt, U.; Mller, A.; Markau, K. C
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    Organic Lab Answer 221

  • 1 pages Organic Lab Answer 23
    • Organic Lab Answer 23
    • University of Florida
    • Organic Chemistry 2 Lab
    • CHM 2212 - Fall 2010
    • 23 + CO Norrish Type I O . h cleavage + CH 2 =CH 2 + CO O H abstraction O C H abstraction CHO + CO Norrish Type II R2 O R1 R2 O h *3 H abstraction R1 OH Bamford, C.H.; Norrish, R.G.W. J. Chem. Soc. 1935, 1504 Norrish, R.G.W.; Bamford, C.H. Nature 1936, 1
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    Organic Lab Answer 23

  • 1 pages Organic Lab Answer 122
    • Organic Lab Answer 122
    • University of Florida
    • Organic Chemistry 2 Lab
    • CHM 2212 - Fall 2010
    • 122 OTs OH H2 O - OTs- O O O + O O O Winstein, S.; Hess, H.V.; Buckles, R.E. J. Am. Chem. Soc. 1942, 64, 2796 Winstein, S.; Buckles, R.E. J. Am. Chem. Soc. 1942, 64, 2780; 2787; 1943, 65, 613 (ii) Flavinium salts Reviews: None. Blackburn, M.; Sankey, G.B.
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    Organic Lab Answer 122

  • 1 pages Organic Lab Answer 226
    • Organic Lab Answer 226
    • University of Florida
    • Organic Chemistry 2 Lab
    • CHM 2212 - Fall 2010
    • 226 Yoshida, K. Electro-oxidation in Organic Chemistry, Wiley: New York, 1984 Hammerich, O.; Parker, V.D. Adv. Phys. Org. Chem. 1984, 20, 55 Mattay, J. Angew. Chem. Int. Ed. 1987, 26, 825 Roth, H.D. Top. Curr. Chem. 1992, 163, 131 Eberson, L. Adv. Phys. O
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    Organic Lab Answer 226

  • 1 pages Organic Lab Answer 128
    • Organic Lab Answer 128
    • University of Florida
    • Organic Chemistry 2 Lab
    • CHM 2212 - Fall 2010
    • 128 + + N2 + N2 Swain, C.G.; Sheats, J.E.; Harbison, K.G. J. Am. Chem. Soc. 1975, 97, 783 Swain, C.G.; Sheats, J.E.; Gorenstein, D.G.; Harbison, K.G. J. Am. Chem. Soc. 1975, 97, 791 Phosphenium ions + P R2 R1 Reviews: Cowley, A.H.; Kemp, R.A. Chem. Rev. 1
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    Organic Lab Answer 128

  • 1 pages Organic Lab Answer 29
    • Organic Lab Answer 29
    • University of Florida
    • Organic Chemistry 2 Lab
    • CHM 2212 - Fall 2010
    • 29 Connor, J.A. J. Organometallic Chem. 1975, 4, 235 (carbenes and carbynes) Moss, R.A.; Jones, M. (eds.) Carbenes, Vol. 1, 2, Wiley: New York, 1975 Moss, R.A. Acc. Chem. Res. 1980, 13, 58 Griller, D.; Nazran, A.S.; Scaiano, J.C. Acc. Chem. Res. 1984, 17,
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    Organic Lab Answer 29

  • 1 pages Organic Lab Answer 134
    • Organic Lab Answer 134
    • University of Florida
    • Organic Chemistry 2 Lab
    • CHM 2212 - Fall 2010
    • 134 Ar O 2 nBuLi HO I Ar Ar Li+ -O O Li - nBuI - nBuOH Ar Hnig, S.; Schweeberg, H.; Schwarz, H. Ann. Chem. 1954, 587, 132 Hnig, S.; Schwarz, H. Ann. Chem. 1956, 599, 131 X X FVT X = O, S, NH Pfister-Guillouzo, G.; Gracian, F.; Senio, A.; Letulle, M.; Ripo
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    Organic Lab Answer 134

  • 1 pages Organic Lab Answer 232
    • Organic Lab Answer 232
    • University of Florida
    • Organic Chemistry 2 Lab
    • CHM 2212 - Fall 2010
    • 232 . Br h O MeO - Br . . + H+ OH O MeO MeO Schepp, N.P. J. Org. Chem. 2004, 69, 4931 Distonic radical cations Reviews: Radom, L.; Bouma, W.J.; Nobes, R.H. Pure Appl. Chem. 1984, 56, 1831 Yates, B.F.; Bouma, W.J.; Radom, L. Tetrahedron 1986, 42, 6225 West
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    Organic Lab Answer 232

  • 1 pages Organic Lab Answer 34
    • Organic Lab Answer 34
    • University of Florida
    • Organic Chemistry 2 Lab
    • CHM 2212 - Fall 2010
    • 34 Barcus, R.L.; Hadel, L.M.; Johnston, L.J.; Platz, M.S.; Savino, T.G.; Scaiano, J.C. J. Am. Chem. Soc. 1986, 108, 3928 (trapping of carbenes via ylide formation) X+ _ Griller, D.; Hadel, L.M.; Nazran, A.S.; Platz, M.S.; Wong, P.C.; Savino, T.G.; Scaiano
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    Organic Lab Answer 34

  • 1 pages Organic Lab Answer 133
    • Organic Lab Answer 133
    • University of Florida
    • Organic Chemistry 2 Lab
    • CHM 2212 - Fall 2010
    • 133 Szwarc, M. Disc. Faraday Soc. 1947, 2, 46 Szwarc, M. J. Chem. Phys. 1951, 16, 319 Farmer, J.B.; Marsden, D.G.H.; Lossing, F.P. J. Chem. Phys. 1955, 23, 403 Errede, L.A.; Landrum, B.F. J. Am. Chem. Soc. 1957, 79, 4952 o-Quinonemethides and p-Quinonemet
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    Organic Lab Answer 133

  • 1 pages Organic Lab Answer 231
    • Organic Lab Answer 231
    • University of Florida
    • Organic Chemistry 2 Lab
    • CHM 2212 - Fall 2010
    • 231 N N X X = CR 3 , NR2 , OMe, Cl, NMe3 + X - e- Nelsen, S.F.; Kessel, C.R.; Brien, D.J. J. Am. Chem. Soc. 1980, 102, 702 ROOC ROOC ROOC N . . N N N COOR + Ph 3 P . . ROOC N _ N COOR + Ph 3 P ROOC N + COOR N ROOC COOR N ROOC N . N N COOR . + Ph 3 P+ PPh3
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    Organic Lab Answer 231

  • 1 pages Organic Lab Answer 33
    • Organic Lab Answer 33
    • University of Florida
    • Organic Chemistry 2 Lab
    • CHM 2212 - Fall 2010
    • : 33 Zupanic, J.J.; Schuster, G.B. J. Am. Chem. Soc. 1980, 102, 5958 Lapin, S.C.; Brauer, B.E.; Schuster, G.B. J. Am. Chem. Soc. 1984, 106, 2092 Ph . . Ph Hadel, L.M.; Platz, M.S.; Scaiano, J.C. J. Am. Chem. Soc. 1984, 106, 283 (quenching of triplet diphe
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    Organic Lab Answer 33

  • 1 pages Organic Lab Answer 132
    • Organic Lab Answer 132
    • University of Florida
    • Organic Chemistry 2 Lab
    • CHM 2212 - Fall 2010
    • 132 Lu're, S.I.; Shemyakin, M.M. J. Gen. Chem. USSR 1947, 17, 1356 Meyer, A.; Bouchet, G. Compt. Rend. 1948, 227, 345 Wittig, G.; Mangold, R.; Felletschin, G. Ann. Chem. 1948, 560, 116 Br CHBr2 CHBr2 2 NaI - 2 NaBr - I2 Br Br . . Br Br Br Cava, M.P.; Napi
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    Organic Lab Answer 132

  • 1 pages Organic Lab Answer 230
    • Organic Lab Answer 230
    • University of Florida
    • Organic Chemistry 2 Lab
    • CHM 2212 - Fall 2010
    • 230 R1 R1 . h N Cl H2 SO4 R2 N+ H R2 Danen, W.C.; Rickard, R.C. J. Am. Chem. Soc. 1972, 94, 3254 O . _ O O . h + Ph Ph CN . Ph Ph B+ A- Ph + A . + Ph . . Ph Ph O+ + ROH Ph Ph . R Ph Ph -. Ph +A Ph H + Ph + Ph CN + Ph . + CN A- Ph _ + Ph . . A- Ph . O Ph N
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    Organic Lab Answer 230

  • 1 pages Organic Lab Answer 32
    • Organic Lab Answer 32
    • University of Florida
    • Organic Chemistry 2 Lab
    • CHM 2212 - Fall 2010
    • 32 Gibbons, W.A.; Trozzolo, A.M. J. Am. Chem. Soc. 1966, 88, 172 (matrix isolation EPR) : N2 H h R-H - N2 . -R . Moritani, I.; Murahashi, S.; Nishino, N.B.; Kimura, K.; Tsubomura, H. Tetrahedron Lett. 1966, 373 (flash photolysis of diazo compounds - no ki
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    Organic Lab Answer 32

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