CHa CH Ortho—→ ← Ortho B Meta Meta FeBr Br P ara Toluene p-Bromotoluene Thomson. Brooks Cole HgC C◇ ortho- Dichlorobenzene meta-Xylene para-Chlorobenzaldehyde 1, 2 disubstituted 1.3 disubstituted 1.4 disubstituted Thomson· Brooks cole
Naming benzenes with more Than two substituents Choose numbers to get lowest possible values List substituents al phabetically with phenate numbers Common names. such as“ toluene”can serve as root name as in tNto trinitrotoluene)
Naming Benzenes With More Than Two Substituents • Choose numbers to get lowest possible values • List substituents alphabetically with hyphenated numbers • Common names, such as “toluene” can serve as root name as in TNT( trinitrotoluene)
Br CH O2N OoN 4-Bromo-1, 2-dimethylbenzene 2-Chloro-1, 4-dinitrobenzene 2, 4, 6-Trinitrotoluene(TNT) ◎ Thomson· Brooks cole OH Br CI C OH 2, 6-Dibromophenol m-Chlorobenzoic acid pThomecn-Brooks Coe
5.5 Chemistry of Benzene Electrophilic aromatic Substitution reactions H E H E: X; NO2; SO3H; R; COR
5.5 Chemistry of Benzene: Electrophilic Aromatic Substitution Reactions H E E: X; NO2 ; SO3H; R; COR; E + H +
5.6 Bromination of Benzenep182 Benzene reacts with slowly with Br, to give bromobenzene ( where br replaces h) This is substitution rather than the rapid addition reaction common to compounds with C=C, suggesting that in benzene there is a higher barrier H B B t Bi t hBr catalyst B H benzene Bromobenzene (Addition product) (substitution product NOT formed Thomson· Brooks Cole
5.6 Bromination of Benzene p182 • Benzene reacts with slowly with Br2 to give bromobenzene (where Br replaces H) • This is substitution rather than the rapid addition reaction common to compounds with C=C, suggesting that in benzene there is a higher barrier