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theodori-Chapter_23___Amines-504943111

theodori-Chapter_23___Amines-504943111 - CHAPTER 23 AMINES...

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23- 23-1 CHAPTER 23 AMINES
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23- 23-2 Structure & Classification Structure & Classification Amines are classified as: 1°, 2°, or , 3° amines: 1°, 2°, or , 3° amines: Amines in which 1, 2, or 3 hydrogens of NH 3 are replaced by alkyl or aryl groups. Methylamine (a 1 °  amine) Dimethylamine (a 2 °  amine) Trimethylamine (a 3 °  amine) CH 3 - NH 2 CH 3 - NH CH 3 - N CH 3 CH 3 CH 3 : : :
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23- 23-3 Structure & Classification Structure & Classification Amines are further divided into aliphatic, aromatic, and heterocyclic amines: Aliphatic Aliphatic amine: amine: An amine in which nitrogen is bonded only to alkyl groups. Aromatic amine: Aromatic amine: An amine in which nitrogen is bonded to one or more aryl groups. Aniline (a 1 °  aromatic amine) N-Methylaniline (a 2 °  aromatic amine) Benzyldimethylamine (a 3 °  aliphatic amine) NH 2 N-H CH 2 - N- CH 3 CH 3 CH 3 : : :
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23- 23-4 Structure & Classification Structure & Classification Heterocyclic amine: Heterocyclic amine: An amine in which nitrogen is one of the atoms of a ring. Pyrrole Piperidine Pyrrolidine Pyridine (heterocyclic aliphatic amines) (heterocyclic aromatic amines) N N N H H N H
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23- 23-5 Structure & Classification Structure & Classification Example: Example: Classify each amino group by type. O O C 6 H 5 N CH 3 COOCH 3 H N H N N CH 3 H (b) ( S )-Coniine (a) Cocaine ( S )-Nicotine (c)
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23- 23-6 Nomenclature Nomenclature Aliphatic amines: replace the suffix - e e of the parent alkane by - amine amine . 1,6-Hexanediamine (S)-1-Phenyl- ethanamine 2-Propanamine NH 2 NH 2 NH 2 H 2 N
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23- 23-7 Nomenclature Nomenclature The IUPAC system retains the name aniline. 3-Methoxyaniline ( m- Anisidine) 4-Methylaniline ( p- Toluidine) Aniline 4-Nitroaniline ( p- Nitroaniline) NH 2 NH 2 CH 3 OCH 3 NH 2 NO 2 NH 2
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23- 23-8 Nomenclature Nomenclature Among the various functional groups discussed in the text, -NH 2 is one of the lowest in order of precedence. COOH H 2 N OH NH 2 H 2 N OH 4-Aminobenzoic acid 2-Aminoethanol (S)-2-Amino-3-methyl- 1-butanol
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23- 23-9 Nomenclature Nomenclature Common names for most aliphatic amines are derived by listing the alkyl groups bonded to nitrogen in one word ending with the suffix - amine amine . CH 3 NH 2   N H Et 3 N NH 2 Triethylamine Dicyclopentylamine Methylamine tert- Butylamine
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23- 10 10 Nomenclature Nomenclature When four groups are bonded to nitrogen, the compound is named as a salt of the corresponding amine. Me 4 N +  Cl  - NCH 2 ( CH 2 ) 1 2 CH 3 Cl  - Ph CH 2 NMe 3 OH - + Benzyltrimethyl- ammonium hydroxide Tetramethy ammonium chloride Tetradecylpyridinium chloride (Cetylpyridinium chloride)
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23- 11 11 Chirality of Amines Chirality of Amines If we consider the unshared pair of electrons on nitrogen as a fourth group, then the arrangement of groups around N is approximately tetrahedral.
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