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CHMB42H3 (16)
Chapter 20

CHMB42 Chapter 20.doc

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University of Toronto Scarborough
Wanda/ Lana

Chapter 20 More About Amines and Heterocyclic CompoundsMore About Amine NomenclatureThe lonepair electrons of the nitrogen atom cause amines to react as bases sharing the lone pair with a proton and as nucleophiles sharing the lone pair with an atom other than protonHeterocyclic Compounds cyclic compounds in which one or more of the atoms of the ring are heteroatoms N O S Se P Si B and AsA saturated cyclic amine a cyclic amine without any double bonds can be named as a cycloalkane using the prefix aza to denote the nitrogen atomSystematic names employ amine as a functional group suffixHeterocycles with oxygen and sulfur heteroatoms have a prefix of oxa for oxygen and thia for sulfurAmines React as Bases and as NucleophilesThe weaker the acid the stronger its conjugate base and the poorer the base as a leaving groupRelative ReactivitiesoRCHFRCHOHRCHOCHRCHNH222322oStrongest acid weaker conjugate base HFHORCHOHNH223Reactions of aldehydes and ketones with primary amines form imines and with secondary amines to form enaminesQuaternary Ammonium Hydroxides Undergo Elimination ReactionsQuaternary Ammonium Ion has the same leaving tendency as a protonated amino group but it does not have an acidic hydrogen that would protonate a basic reactant it can undergo a reaction wit
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