Chemistry Chapter 13
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1 Chemistry 2100 Chapter 13
2 Discovering Aromatics C C C C C C C 2 3 C C C C C C 3 De war 1867 Ladenburg 1878 C 6 6 Br 2 / Fe (-Br) C 6 5 Br Br 2 / Fe (-Br) C 6 4 Br 2 C 3 C 3 C 2 C 2 C Å 1.33 Å 1.39 Å
3 Aromatics
4 Resonance
5 Resonance
6 Resonance
7 Resonance
8 Resonance
9 Resonance
10 Resonance
11 Resonance
12 Resonance
13 Graphene
14 Carbon Nanotubes
15 Nomenclature for Arenes Many common names retained PA Naphthalene Anthracene Phenanthrene Benzo[a]pyrene
16 Nomenclature Monosubstituted alkylbenzenes are named as derivatives of benzene; for example, ethylbenzene. The IUPAC system retains certain common names for several of the simpler monosubstituted alkylbenzenes. C 2 C 3 C 3 C=C 2 Ethylbenzene Toluene Styrene
17 Nomenclature The common names for these monosubstituted benzenes are also retained O OC 3 N 2 O C- O C-O Phenol Anisole Aniline Benzaldehyde Benzoic acid Phenyl group (C or Ph-): The substituent group derived by removal of an from benzene. C Phenyl group 1-Phenylcyclohexene 4-Phenyl-1-butene
18 Nomenclature When two substituents occur on a benzene ring, three isomers are possible; they may be located by: numbering the atoms of the ring or using the locators ortho (o), meta (m), and para (p). 1 COO Br 2 1 C C 2 C Bromobenzoic acid (o-bromobenzoic acid) C 3 1,3-Dimethylbenzene (m-xylene) 3 1 Cl 1-Chloro-4-ethylbenzene (p-chloroethylbenzene) 2
19 Aromatic Reactions
20 Reactions of Benzene By far the most characteristic reaction of aromatic compounds is substitution at a ring carbon. This reaction is called aromatic substitution. Some groups that can be introduced directly on the ring are the halogens, the nitro (-NO 2 ) group, and the sulfonic acid (- SO 3 ) group. alogenation: FeCl + Cl 3 2 Cl + Cl Benzene Chlorobenzene 20!
21 Phenols The functional group of a phenol is a hydroxyl ( -O) group bonded to a benzene ring. Name substituted phenols either as derivatives of phenol or by common names. O O O O O O Phenol 3-Methylphenol (m-cresol) 1,2-Benzenediol (Catechol) O 1,3-Benzenediol (Resorcinol) O 1,4-Benzenediol (ydroquinone) 21!
22 Noteworthy Phenols O Cl O O Cl C 3 O eugenol O Cl Cl C 2 Cl Cl O hexachlorop hene hexylresorc inol O O O O O CON 2 O Cl O C 3 N(C3 ) 2 O O tetrahydrocannabinol aur eomycin
23 Phenol Acidity Acidity: O C 3 C O > > O C 3 O acids > thiols ~ phenols > water ~ alcohols Comparative acidities of 0.1 M aqueous solutions of representative acids A Cl OAc PhO EtS EtO O K a % ionized [ 3 O + ], M p ~ ~100 ~ acids > phenols ~ thiols > water ~ alcohols
24 Phenols as Antioxidants Autoxidation C 2 C=C-C Section of a fatty acid hydrocarbon chain light or heat C 2 C=C-C A carbon radical O-O C 2 C=C-C + O-O C 2 C=C-C Oxygen is a diradical A hydroperoxy radical O-O C 2 C=C-C + C 2 C=C-C Section of a new fatty acid hydrocarbon chain O-O- C 2 C=C-C -C 2 A hy droperoxide + C 2 C=C-C A new carbon radical
25 Natural Phenolic Antioxidants C 3 C C 3 O 3 C 3 O C 3 C 3 C 3 C 3 Vitamin E (α-tocopherol) ( α toc opherol) O O Resveratrol O
26 Man-made Phenolic Antioxidants O O O C 3 BT OC 3 BA O C OC 3 me thyl par aben
27 Phenols as Weapons?
28 COO C 2 C N 2 p henyla lanine
29 COO C 2 C N 2 p henyla lanine
30 COO C 2 C N 2 [O] COO C 2 C N 2 p henyla lanine O tyrosine
31 COO C 2 C N 2 [O] COO C 2 C N 2 p henyla lanine O tyrosine [O] O COO C 2 C N 2 O L-DOPA
32 COO C 2 C N 2 [O] COO C 2 C N 2 p henyla lanine O tyrosine [O] O COO C 2 C N 2 O L-DOPA
33 COO C 2 C N 2 [O] COO C 2 C N 2 p henyla lanine O tyrosine [O] COO O C 2 C 2 N 2 O C 2 C N 2 -CO 2 O dopamine O L-DOPA
34 COO C 2 C N 2 [O] COO C 2 C N 2 p henyla lanine O tyrosine [O] COO O C 2 C 2 N 2 O C 2 C N 2 -CO 2 O dopamine O L-DOPA [O] O O C C 2 N 2 O nor epinephrine
35 COO C 2 C N 2 [O] COO C 2 C N 2 p henyla lanine O tyrosine [O] COO O C 2 C 2 N 2 O C 2 C N 2 -CO 2 O dopamine O L-DOPA [O] O O O C C 2 N 2 "C 3 " O C C 2 N C 3 O nor epinephrine O epinephrine
36 COO C 2 C N 2 [O] COO C 2 C N 2 p henyla lanine O tyrosine [O] COO O C 2 C 2 N 2 O C 2 C N 2 -CO 2 O dopamine O L-DOPA [O] O O O C C 2 N 2 "C 3 " O C C 2 N C 3 O nor epinephrine O epinephrine
37 C C N "phenethylamine"
38 O C C N C 3 C 3 ephedrine (ephedra) / pseudoephedrine
39 O C C N C 3 C 3 ephedrine (ephedra) / pseudoephedrine
40 C C N 2 C 3 C 3 methylenedioxymethamphetamine / MDMA / Ecstacy
41 O C2 C N C 3 O C 3 methylenedioxymethamphetamine / MDMA / Ecstacy
42 O C2 C N C 3 O C 3 methylenedioxymethamphetamine / MDMA / Ecstacy
43 O C2 C N C 3 O C 3 methylenedioxymethamphetamine / MDMA / Ecstacy
44 Organic Food Dye: Carminic Acid O O O O COO O O O carminic ac id O
45 Aromatic eterocycles O C N 2 N N N C 3 niacin (B 3 ) / nicotinamide nicotine N N 2 Cl N C 2 S C 3 C 2 C 2 O ()C 3 N O N C 3 C 3 N O N N thiamine (B 1 ) C 3 caffeine (theobromine)
46 eterocycles store life s information () C 3 O Sugar N N O (U) T = A
47 () C 3 O N N Sugar N N O N N N Sugar (U) T = A
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