310_21 - Organic Lecture Series CH 310 N LECTURE 21...

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Organic Lecture Series 1 CH 310 N LECTURE 21 Textbook Assignment: Chapter 23 Amines Homework (for credit): Problem Set – 7 Posted Today’s Topics: Structure; properties; nomenclature Notice & Announcements: EXAM 2: Pick up @ office hrs Organic Lecture Series 2 Amines Amines Epinephrine (adrenaline) Chapter 23
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Organic Lecture Series 3 Structure & Classification Structure & Classification • Amines are classified as 1°, 2 , 2 °, or , 3 , or , 3 ° amines: amines: amines in which 1, 2, or 3 hydrogens of NH 3 are replaced by alkyl or aryl groups 2 o o Organic Lecture Series 4 • 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 : Structure & Classification Structure & Classification
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Organic Lecture Series 5 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 Structure & Classification Structure & Classification Organic Lecture Series 6 O OC 6 H 5 N CH 3 COOCH 3 H N H N N 3 H (b) ( S )-Coniine (a) Cocain e ( S )-Nicotine (c) Structure & Classification Structure & Classification Coniine is a poisonous alkaloid found in poison hemlock and the Yellow Pitcher Plant, and contributes to hemlock's fetid smell. It is a neurotoxin which disrupts the peripheral nervous system. Caffeine
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Organic Lecture Series 7 • Aliphatic amines: replace the suffix - e of the parent alkane by - amine amine 1,6-Hexanediamine (S)-1-Phenyl- ethanamine 2-Propanamine NH 2 2 2 H 2 N Nomenclature Nomenclature Organic Lecture Series 8 Nomenclature Nomenclature • The IUPAC system retains the name aniline: 3-Methoxyaniline ( m- Anisidine) 4-Methylaniline ( p- Toluidine) Aniline 4-Nitroaniline ( p- Nitroaniline) 2 2 CH 3 OCH 3 2 NO 2 2
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Organic Lecture Series 9 • 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 4-Aminobenzoic acid 2-Aminoethanol (S)-2-Amino-3-methyl- 1-butanol Nomenclature Nomenclature Organic Lecture Series 10 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 2 N H Et 3 N 2 Triethylamine Dicyclopentylamine Methylamine tert- Butylamine Nomenclature Nomenclature
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Organic Lecture Series 11 • 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 ) 12 CH 3 - Ph CH 2 NMe 3 OH - + Benzyltrimethyl- ammonium hydroxide Tetramethy chloride
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310_21 - Organic Lecture Series CH 310 N LECTURE 21...

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