Chapter 14: Aromatic Compounds CH 14-1: Nomenclature of Substituted Benzene Nomenclature of substituted benzenes What is so special about the “aromaticity” of benzene rings? (conjugation, delocalization, resonance, Huckel’s Rule) Examples of aromatic compounds and ions IR & NMR of benzene

Nomenclature of Benzene Mono-Substituted Benzene (“benzene” is the parent name): substituent name + benzene Abbreviations for the phenyl ring as a substituent: -Ph -C6H5 -f Cyclopropyl benzene Chloro benzene Ethyl benzene Phenyl lbenzene

Nomenclature of Benzene Benzene as a substituent group: (2R,3R)- 3-phenyl-2-pentanol trans-4-chloro-1-phenyl-1-butene

Nomenclature of Benzene Common Names (you must learn these): phenol benzaldehyde toluene benzoic acid benzyl alcohol acetophenone benzyl bromide

Nomenclature of Benzene Di-substituted benzene. ID the “parent”. You can use “benzene”, or combine a substituent with benzene as the parent. Then use the lowest numbering system or ortho, meta, para designations: 1-bromo-3-chloro benzene, or 3-chloro-bromobenzene, or meta-chloro-bromobenzene 4-ethyl phenol, or para-ethyl phenol

Nomenclature of Benzene Multi-substituted benzene (3 or more substituents). ID the “parent”. You can use “benzene”, or combine a substituent with benzene as the parent. Then use the lowest numbering system (not o, m, p), listing substituents alphabetically: 1-bromo-3-ethyl-4-methyl benzene OR 3-ethyl-4-methyl-bromobenzene 4-bromo-2-ethyl toluene