2014_L9_PiBondsElectrophiles3

H2so4ch3oh o chm1321 ch3 h3 c o h2 c nh4hso4 ch3 ch3

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Unformatted text preview: –  aroma(c ketones O 1) NaCN/OH –/H2O 2) H 3O+ /H2O OH OH CN O IBUPROFEN CHM1321 π bonds as electrophiles 6 base catalysis CH3COCH3 + HCN CH3 NC OH CH3 aq. H2SO4/CH3OH O CHM1321 CH3 H3 C O H2 C - NH4HSO4 CH3 CH3 NC OH CH3 O CH3 CH3 O O OCH3 OCH3 OCH3 π bonds as electrophiles PMMA 7 •  reac(on is reversible in base: O H OH/H2O O one step (very fast) + C N + H 2O CN CHM1321 π bonds as electrophiles 8 •  “hidden” carbonyl groups: O O O O oxonium ion CHM1321 π bonds as electrophiles 9 •  red = atoms; green = bonds 1 5 O 6 2 O 7 3 + Br Br 4 CHM1321 π bonds as electrophiles 10 OH OH H O H H H NaCN/OH –/H2O ? OH OH CHM1321 π bonds as electrophiles 11 •  cyanohydrins are useful because: –  added a carbon –  added func(onality •  example: can be hydrolyzed to carboxylic acids CHM1321 π bonds as electrophiles 12 O 1. HCN C CH3CH2 A.  B.  C.  D.  H 2. H3O + 2 ­Hydroxybutanenitrile 2 ­Oxobutanenitrile 2 ­Hydroxybutanoic acid 2 ­Oxobutanoic acid CHM1321 π bonds as electrophiles 13 •  HCN: common natural poison –  used by plant in defensive mechanisms •  example: Cassava –  contains 2 glucosides: linamarin + lotaustralin CHM1321 π bonds as electr...
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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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