lecture 24 - Chapter 24 Amines and Heterocycles Based on...

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Chapter 24. Amines and Heterocycles Based on McMurry’s Organic Chemistry , 7 th edition
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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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3 Why this Chapter? Amines and carbonyl compounds are the most abundant and have rich chemistry In addition to proteins and nucleic acids, a majority of pharmaceutical agents contain amine functional groups
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4 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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5 Quaternary Ammonium Ions A nitrogen atom with four attached groups is positively charged Compounds are quaternary ammonium salts
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6 IUPAC Names – Simple Amines For simple amines, the suffix - amine is added to the name of the alkyl substituent
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7 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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8 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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9 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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10 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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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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12 24.2 Properties of 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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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 Amines Form H-Bonds Amines with fewer than five carbons are water- soluble Primary and secondary amines form hydrogen bonds, increasing their boiling points
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15 24.3 Basicity of Amines The lone pair of electrons on nitrogen makes amines basic and nucleophilic They react with acids to form acid–base salts and they react with electrophiles
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16 Relative Basicity Amines are stronger bases than alcohols, ethers, or water
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