Chapter24 - Chapter 24. Amines Based on McMurrys Organic...

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Chapter 24. Amines Based on McMurry’s Organic Chemistry , 6 th edition ©2003 Ronald Kluger Department of Chemistry University of Toronto
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Based on McMurry, Organic Chemistry, Chapter 24, 6th 2 Amines – Organic Nitrogen Compounds Organic derivatives of ammonia, NH 3 , Nitrogen atom with a lone pair of electrons, making amines both basic and nucleophilic Occur in plants and animals
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Based on McMurry, Organic Chemistry, Chapter 24, 6th 3 24.1 Naming Amines Alkyl-substituted (alkylamines) or aryl-substituted (arylamines) Classified: 1° (RNH 2 ), methyl (CH 3 NH 2 ), 2° (R 2 NH), 3° (R 3 N)
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Based on McMurry, Organic Chemistry, Chapter 24, 6th 4 Quaternary Ammonium Iions A nitrogen atom with four attached groups is positively charged Compounds are quaternary ammonium salts
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Based on McMurry, Organic Chemistry, Chapter 24, 6th 5 IUPAC Names – Simple Amines For simple amines, the suffix - amine is added to the name of the alkyl substituent
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Based on McMurry, Organic Chemistry, Chapter 24, 6th 6 IUPAC Names – “-amine” Suffix The suffix - amine can be used in place of the final - e in the name of the parent compound
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Based on McMurry, Organic Chemistry, Chapter 24, 6th 7 IUPAC Names – Amines With More Than One Functional Group Consider the NH 2 as an amino substituent on the parent molecule
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Based on McMurry, Organic Chemistry, Chapter 24, 6th 8 IUPAC Names – Multiple Alkyl Groups Symmetrical secondary and tertiary amines are named by adding the prefix di - or tri - to the alkyl group
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Based on McMurry, Organic Chemistry, Chapter 24, 6th 9 IUPAC Names – Multiple, Different Alkyl Groups Named as N -substituted primary amines Largest alkyl group is the parent name, and other alkyl groups are considered N -substituents
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Based on McMurry, Organic Chemistry, Chapter 24, 6th 10 Common Names Alkylamines do not have common names unless they are biological molecules Simple arylamines have common names
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Based on McMurry, Organic Chemistry, Chapter 24, 6th 11 Common Names of Heterocyclic Amines If the nitrogen atom occurs as part of a ring, the compound is designated as being heterocyclic Each ring system has its own parent name
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Based on McMurry, Organic Chemistry, Chapter 24, 6th 12 24.2 Structure and Bonding in Amines Bonding to N is similar to that in ammonia N is sp 3 -hybridized C–N–C bond angles are close to 109° tetrahedral value
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Based on McMurry, Organic Chemistry, Chapter 24, 6th 13 Chirality Is Possible (But Not Observed) An amine with three different substituents on nitrogen is chiral (in principle but not in practice): the lone pair of electrons is the fourth substituent Most amines that have 3 different substituents on N are not resolved because the molecules interconvert by pyramidal inversion
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14 24.3 Properties and Sources of Amines Simple methylated amines from reaction of NH 3 with CH 3 OH and alumina catalyst
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Chapter24 - Chapter 24. Amines Based on McMurrys Organic...

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