CNGNGE JOHN MCMURRY CHAPTER9 Aromatic Compounds TH IRD EDITION Organic Chemistry with Biological Applications
CHAPTER 9 Aromatic Compounds
Early Days of Organic Chemistry Aromatic Compounds Formerly used to describe fragrant substances such as benzaldehyde (from cherries,peaches,and almonds), toluene (from Tolu balsam),and benzene (from coal distillate) CH3 Benzene Benzaldehyde Toluene Now used to refer to the class of compounds that contain six-membered benzene-like rings with three double bonds
Aromatic Compounds ▪ Formerly used to describe fragrant substances such as benzaldehyde (from cherries, peaches, and almonds), toluene (from Tolu balsam), and benzene (from coal distillate) ▪ Now used to refer to the class of compounds that contain six-membered benzene-like rings with three double bonds Early Days of Organic Chemistry
Present Days of Organic Chemistry Aromatic Compounds Benzene Found to cause bone marrow depression Leads to leukopenia,or lowered white blood cell count,on prolonged exposure Many naturally occurring compounds are aromatic in part Steroidal hormone estrone Atorvastatin(Lipitor)-a cholesterol-lowering drug CH(CH3)2 H OH H OH CH3 CO2H HO Estrone Atorvastatin (Lipitor)
Aromatic Compounds ▪ Benzene ▪ Found to cause bone marrow depression ▪ Leads to leukopenia, or lowered white blood cell count, on prolonged exposure ▪ Many naturally occurring compounds are aromatic in part ▪ Steroidal hormone estrone ▪ Atorvastatin (Lipitor) – a cholesterol-lowering drug Present Days of Organic Chemistry
9-1 Naming Aromatic Compounds Aromatic substances have acquired nonsystematic names Nonsystematic names :EC Common Names of Some Aromatic Compounds are discouraged but Structure Name Structure Name allowed by IUPAC CH3 Toluene CHO Benzaldehyde (bp 111C) (bp 178C) Common name for methylbenzene is OH Phenol CO>H Benzoic acid toluene (mp 43C) (mp122C) Common name for NH2 Aniline ortho-Xylene hydroxybenzene is (bp184G) (bp 144C) phenol CH3 Acetophenone Styrene Common name for (mp 21C) (bp145C) CH3 aminobenzene is aniline
Aromatic substances have acquired nonsystematic names ▪ Nonsystematic names are discouraged but allowed by IUPAC ▪ Common name for methylbenzene is toluene ▪ Common name for hydroxybenzene is phenol ▪ Common name for aminobenzene is aniline 9-1 Naming Aromatic Compounds
Naming Aromatic Compounds TABLE9.1 Common Names of Some Aromatic Compounds Structure Name Structure Name CH3 Toluene CHO Benzaldehyde (bp 111 C) (bp178C) OH Phenol CO2H Benzoic acid (mp 43C) (mp122C) NH2 Aniline CH3 ortho-Xylene (bp 184C) (bp 144 C) CH3 0 Acetophenone H Styrene C (mp 21 C) (bp 145C) CH3 H
Naming Aromatic Compounds