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CHMB42H3 (16)
Chapter 21

CHAPTER 21 - Textbook Notes.docx

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University of Toronto Scarborough
Lana Mikhaylichenko

CHAPTER 21: MORE ABOUT AMINES • HETEROCYCLIC COMPOUNDS  Amines – compounds in which one or more of the hydrogens of ammonia (NH ) have b3en replaced by an alkyl group.  The lone-pair electros 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 a proton.  Some amines are heterocyclic compounds (or heterocycles) – cyclic compounds in which one or more of the atoms of the ring are heteroatoms. 21.1 More about the Acid-Base Properties of Amines  Amines have very high pK valaes. 21.3 Amines React as Bases and as Nucleophiles  The lone pair on the nitrogen of an amine causes it to be nucleophilic as well as basic. 10.8 Amines Do Not Undergo Substitution or Elimination Reactions  The weaker the acid, the stronger its conjugate base and the poorer the base is as a leaving group.  The leaving group of an amine ( NH ) 2s such a strong base that amines cannot undergo substitution or elimination reactions.  The lone pair on the nitrogen atom a
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