2014_L8_PiBondsElectrophiles2

Ph mgbr o 2 h3 o oh a oh c chm1321 b bonds as

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Unformatted text preview: 1) R 1 C CHM1321 C R2 O R2 OH Mg Br 2) H 3O+ /H2O R3 R1 OH C R2 π bonds as electrophiles H R1 R3 8 OH 1. Ph MgBr O 2. H3 O+ OH A OH C CHM1321 B π bonds as electrophiles D O 9 •  theore(cal technique for designing synthesis •  work backwards from desired target •  imaginary process: break molecules apart and re ­connect them •  use a special arrow to show disconnec(on: CHM1321 π bonds as electrophiles 10 OH CHM1321 π bonds as electrophiles 11 OH N aBH4 O B r Mg Br Mg A B C ? O Br OH CHM1321 π bonds as electrophiles 13 •  more reac(ve than Grignards: used when Grignards yield poor results •  very tricky: must be prepared and handled under an inert atmosphere •  forma(on: metal ­halogen exchange R Br CHM1321 + 2 Li R π bonds as electrophiles Li + LiBr 14 •  alkyl lithiums are REALLY strong bases •  oaen used in the prepara(on of other nucleophiles –  e.g. butyl lithium, BuLi CHM1321 π bonds as electrophiles 15 •...
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This note was uploaded on 03/12/2014 for the course CHM 1321 taught by Professor Flynn during the Spring '08 term at University of Ottawa.

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