Chemistry Chapter 16
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1 Chemistry 2100 Chapter 16
2 Amines Amines are nitrogen-containing compounds
3 Structure and Classification Amines are classified as 1, 2, or 3 depending on the number of carbon groups bonded to nitrogen. C 3-2 C 3 --C 3 Methylamine Dimethylamine (a 1 amine) (a 2 amine) C 3 C 3 --C 3 Trimethylamine (a 3 amine) Aliphatic amine: All carbons bonded to nitrogen are derived from alkyl groups. See the three above. Aromatic amine: One or more of the groups bonded to nitrogen are aryl groups. 2 -C 3 C 3 C 2 --C 3 Aniline (a 1 aromatic amine) -Methylaniline (a 2 aromatic amine) Benzyldimethylamine (a 3 aliphatic amine)
4 Structure and Classification eterocyclic amine: An amine in which the nitrogen atom is part of a ring. eterocyclic aliphatic amine: A heterocyclic amine in which the ring is saturated (has no C=C bonds). eterocyclic aromatic amine: The amine nitrogen is part of an aromatic ring. Pyrrolidine Piperidine (heterocyclic aliphatic amines) Pyridine Pyrimidine Imidazole Purine (heterocyclic aromatic amines)
5 omenclature IUPAC names We derive IUPAC names for aliphatic amines just as we did for alcohols. Drop the final -e of the parent alkane and replace it by -amine. Use a number to locate the amino group on the parent chain C 3 CC Propanamine Cyclohexanamine 1,6-exanediamine
6 Physical Properties Amines are polar compounds: Both 1 and 2 amines have - bonds, and can form hydrogen bonds with one another. 3 Amines have no - bond and cannot form hydrogen bonds with one another.
7 Boiling Points 3 (bp -33 C) 2 O (bp +100 C) C 3 C 3 (bp -88 C) C 3 2 (bp -7 C) C 3 O (bp +65 C) C 3 C 2 C 2 2 (bp 48 C) C 3 C 2 C 3 (bp 35 C) (C 3 ) 3 (bp 3 C)
8 Odor Like ammonia, low-molecular-weight amines have very sharp, penetrating odors. Trimethylamine, for example, is the pungent principle in the smell of rotting fish. Two other particularly pungent amines are 1,4- butanediamine (putrescine) and 1,5- pentanediamine (cadaverine) ,4-Butanediamine (Putrescine) 2 2 1,5-Pentan ediamine (Cadaverine)
9 Basicity of Amines + - C 3 -: + -O- C 3 -- : O- Methylamine Methylammonium (a base) hydroxide : : : : Class pk b Example ame Aliphatic Ammonia Aromatic C 3 C 2 2 C Ethanamine Aniline Stronger base Weaker base
10 Ammonium Salts R R" free base + Cl - a + O - R R" Cl ammonium salt (hydrochloride)
11 Alkaloids C 3 C 3 Cl COOC 3 (S)-( )-nicotine C2 C 2 C 3 (S)-(+)-coniine (+)-coniine O C O ( )-cocaine hydrochloride O O ( )-strychnine
12 itrosation ao 2 + Cl (aq) O O + acl (aq) nitrous ac id R 2 (1 ) Cl + O O R Cl R O + (-2 2 O) R + O O (2 ) diazonium salt Cl 2 O 2 O (-Cl ) R O + 2 O nit rosoamine
13 ao 2 + Cl (aq) O O + acl (aq) nitrous ac id R 2 (1 ) Cl + O O R Cl R O + (-2 2 O) R + O O (2 ) diazonium salt Cl 2 O 2 O (-Cl ) R O + 2 O nit rosoamine
14 ao 2 + Cl (aq) O O + acl (aq) nitrous ac id R 2 (1 ) Cl + O O R Cl R O + (-2 2 O) R + O O (2 ) diazonium salt Cl 2 O 2 O (-Cl ) R O + 2 O nit rosoamine
15 ao 2 + Cl (aq) O O + acl (aq) nitrous ac id R 2 (1 ) Cl + O O R Cl R O + (-2 2 O) R + O O (2 ) diazonium salt Cl 2 O 2 O (-Cl ) R O + 2 O nit rosoamine
16 ao 2 + Cl (aq) O O + acl (aq) nitrous ac id R 2 (1 ) Cl + O O R Cl R O + (-2 2 O) R + O O (2 ) diazonium salt Cl 2 O 2 O (-Cl ) R O + 2 O nit rosoamine
17 ao 2 + Cl (aq) O O + acl (aq) nitrous ac id R 2 (1 ) Cl + O O R Cl R O + (-2 2 O) R + O O (2 ) diazonium salt Cl 2 O 2 O (-Cl ) R O + 2 O nit rosoamine
18 ao 2 + Cl (aq) O O + acl (aq) nitrous ac id R 2 (1 ) Cl + O O R Cl R O + (-2 2 O) R + O O (2 ) diazonium salt Cl 2 O 2 O (-Cl ) R O + 2 O nit rosoamine
19 ao 2 + Cl (aq) O O + acl (aq) nitrous ac id R 2 (1 ) Cl + O O R Cl R O + (-2 2 O) R + O O (2 ) diazonium salt Cl 2 O 2 O (-Cl ) R O + 2 O nit rosoamine
20 Azo Dyes Cl + Me 2 (-Cl ) 0 C Me 2 Butter Ye llow
21 Cl + Me 2 (-Cl ) 0 C Me 2 Butter Ye llow
22 Cl + Me 2 (-Cl ) 0 C Me 2 Butter Ye llow
23 Cl + Me 2 (-Cl ) 0 C Me 2 Butter Ye llow
24 O + Cl SO 3 (-Cl ) 0 C O SO 3 Orange II
25 O + Cl SO 3 (-Cl ) 0 C O SO 3 Orange II
26 O + Cl SO 3 (-Cl ) 0 C O SO 3 Orange II
27 O + Cl O SO 32 (-Cl ) 0 C O O SO 32 American Orange II Flag Red
28 2 O O 2 O 3 S SO 3 Direct Blue 2B O 3 S SO 3
29 2 O O 2 O 3 S SO 3 Direct Blue 2B O 3 S SO 3 2 O O 2 O O 3 S SO 3 Diamine Green B
30 eterocyclic Amines C 2 C 2 C 3 coniine nicotine C 3 C 3 O O quinine
31 C C 2 C 3 C C 2 C 3 C 3 C C 2 C 3 C 2 C 3 Fe Mg C 3 C 3 C 2 C 2 C 3 C 3 C 2 COO C 2 COO O C 3 OOC O O heme chlorop hyll a
32 nicotinamide / niacin (B 3 )
33 Morphine Codeine eroin
34 Poison Dart Frogs epibatidine Cl
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