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2014_L9_PiBondsElectrophiles3

Posive charge on the c atom weaker electrophile less

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Unformatted text preview: ophiles 14 H OH HO HO HO H H O CN OH H H 3C HO CN H 3C glucose + CH 3 CH 3 O H 3C CHM1321 π bonds as electrophiles CH 3 + HCN 15 •  nitrogen ­based analogues of carbonyl compounds •  react like carbonyls with nucleophiles •  N is less EN than O: smaller par(al posi(ve charge on the C atom –  weaker electrophile, less reac(ve N N imine CHM1321 π bonds as electrophiles 16 •  Because of the reduced reac(vity, we need to “ac(vate” the imine towards nucleophilic addi(on •  Carry out reac(ons in acidic condi(ons: N H 3O+ N H N H H 2O imine CHM1321 π bonds as electrophiles 17 CHM1321 π bonds as electrophiles 18 •  Reduc(on with sodium cyanoborohydride: –  NaBH3CN is used because it’s stable in acid CHM1321 π bonds as electrophiles 19 •  slight modifica(on to the two ­step process: 1.  nucleophilic addi(on 2.  leaving group elimina(on •  a.k.a. Nucleophilic Addi(on – Elimina(on •  general mechanism: CHM1321 π bonds as electrophiles 20 CHM1321 π bonds as electrophiles 21 CHM1321 π bonds as electrophiles 22 O O C CH3CH2 A.  B.  C.  D.  CH3CH2NH2 C O CH2CH3 N,N ­Diethylpropanamide + propanoic acid N ­Ethylpropanamide + propanoic acid N ­Ethylethanamide + ethanoic acid N,N ­Diethylethanamide + ethanoic acid CHM1321 π bonds as electrophiles 23...
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