Lecture 8 - Amines Introduction and Properties Part...

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Unformatted text preview: Amines Introduction and Properties Part 1-Chapter 24 1 Overview Introduction Nomenclature Physical properties 2 ABENOR Nitrogen forms 3 covalent bonds and has a lone pair 1s 2s 2p 1s 2s 2p N 7+ C 6+ 3 1s 2p 1s 2p O 8+ F 9+ 2s 2s Some typical acyclic alkyl amines ethylamine rimethylamine ( shy 4 Methylamine Trimethylamine ( fishy ) Benadryl (diphenhydramine) H odourless + Antihistamine ( fishy ) Alkaloids Naturally occuring amines, found primarily in plants, are called alkaloids eg nicotine, cocaine, morphine, heroin, quinine.. Alkaloids = alkaline basic! 5 Amines are Bronsted Bases Alkaloids-Natures Curse or Blessing, Manfred Hesse (2000) N H + .. Amine heterocycles 6 Atropine dilates Pupils 7 Compare with Aromatic amines NH 2 8 N Resonance forms pyridine aniline Recall: Difference between nomenclature for amines and alcoh ol s Alcohols Ethers 1 amines O H 2 HOR RX O H 2 ROR 2 RX NH 3 RNH 2 RX 9 2 amines 3 amines 4 ammonium salt NH 3 R 2 NH 2 RX NH 3 NR 3 3 RX NH 3 R 4 N X 4 RX +- Amines and alcohols 1 alcohol 1 amine NH 2 N 10 2 alcohol still a 1 amine! 2 amine OH NH 2 H 3 alcohol Still a 1 amine! 3 amine OH NH 2 N Rules of Nomenclature For Alcohols- # of carbons attached to the carbon-bearing hydroxyl determines whether it is primary, secondary or tertiary. 11 For Amines- # of carbons attached to nitrogen determines whether it is primary, secondary or tertiary.. Unlike oxonium salts. ammonium salts are stable at RT O R R R X +- Unstable! R 12 N R R R X +- Stable! Why? Electronegativity! Nitrogen is less electronegative (3.0) than Oxygen (3.5). Nitrogen is better able to support the positive charge. Naturally occuring quaternary ammonium compounds Muscarine Acetylcholine 13 Ivory funnel mushroom Neurotransmitter required for activating muscle Summary: Alcoh ol s and ethers are organic derivatives of water Amines are organic derivatives of 14 Amines are organic derivatives of ammonia (NH 3 ) Amines form stable ammonium salts. Nomenclature of Simple Amines Methylamine Dimethylamine C H 3 NH 2 C H 3 N H CH 3 15 Trimethylamine Tetramethylammonium chloride C H 3 N CH 3 CH 3 N + CH 3 CH 3 C H 3 CH 3 Cl Nomenclature: Some examples C H 3 N CH 2 C H 3 C O CH 3 16 C H 3 N C H 2 C H 3 C H H CH 3 N H 2 CH 2 C CH 3 H H Degree of Unsaturation For nitrogen-containing compounds: have to subtract one H per Nitrogen atom Degree of unsaturation = 2n +2 hydrogens Observed # hydrogens (for n carbons) 2 Example: 3 3 3 C 3 H 9 N Degree of unsaturation = 8 (9 -1) = 2 Physical Properties 1) Trends in m.p. and b.p. (See next slide) 2) Solubility in water: like alcohols, lower amines re miscible with water (< C 18 are miscible with water (< C 5 )....
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Lecture 8 - Amines Introduction and Properties Part...

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