Chapter_20 - Chapter 20 Amines Nomenclature Primary amines...

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Chapter 20 Amines
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Chapter 20 2 Nomenclature Primary amines are named in systematic (IUPAC) nomenclature by replacing the -e of the corresponding parent alkane with - amine In common nomenclature they are named as alkylamines Simple secondary and tertiary amines are named in common nomenclature by designating the organic groups separately in front of the word amine In systematic nomenclature, the smaller groups on the amine nitrogen are designated as substituents and given the locant N
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Chapter 20 3 In IUPAC nomenclature the substitutent -NH 2 is called the amino group Aryl Amines The common arylamines have the following names:
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Chapter 20 4 Heterocyclic Amines The important heterocylcic amines have common names In IUPAC nomenclature the prefixes aza -, diaza- and triaza - are used to indicate that nitrogen has replaced carbon in the corresponding hydrocarbon The nitrogen is assigned position 1 and the ring is numbered to give the lowest overall set of locants to the heteroatoms
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Chapter 20 5 Physical Properties and Structure of Amines Primary and secondary amines can form hydrogen bonds to each other and water Tertiary amines cannot form hydrogen bonds to each other but can form hydrogen bonds to hydrogen bond donors such as water Tertiary amines have lower boiling points than primary or secondary amines of comparable molecular weights Low molecular weight amines tend to be water soluble whether they are primary, secondary or tertiary
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Chapter 20 6
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Chapter 20 7 Structure of Amines The nitrogen atom in an amine is sp 3 hybridized The three groups and the unshared electron pair around nitrogen result in a tetrahedral geometry If only the location of the groups (and not the unshared electron pair) are considered, the shape of the amine is trigonal pyramidal Partial negative charge is localized in the region of the nonbonding electrons It is usually impossible to resolve amine enantiomers that are chiral at nitrogen because they interconvert rapidly The interconversion occurs through a pyramidal or nitrogen inversion involving the unshared electron pair
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Chapter 20 8 Quaternary ammonium salts can be resolved into enantiomers Chiral quaternary ammonium salts cannot undergo nitrogen inversion because they lack an unshared electron pair on the nitrogen atom
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Chapter 20 9 Basicity of Amines: Amine Salts Amines are weak bases
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Chapter_20 - Chapter 20 Amines Nomenclature Primary amines...

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