CONF 03500 AlkyneExercises¬ BenzeneExercises¬ TEXT HEAD Benzene¬ LINE¬ TITL Benzene Introduction¬ 00 PLAN¬ IGNO Benzene is a six membered ring with alternating double bonds.¬ CIMG 000 100 benzene¬IGNO However, benzene does not act like similar alkenes, failing to brominate when ¬CIMG -03 003 br2¬IGNO is added. In fact, in reality benzene does not even consist of alternating double bonds. It is a resonance hybrid, with each bond having the character of one and a half bonds.¬LINE¬LINE¬IGNO Benzene has the character of one and a half bonds¬LINE¬ CIMG 000 100 benzenepartial¬LINE¬IGNO Resonance for Bezene¬LINE¬ CIMG 000 130 benzeneresonance¬LINE¬IGNO For convenience benzene is drawn ¬LINE¬CIMG 000 030 benzeneshort¬IGNO or perhaps more correctly as ¬CIMG -30 030 benzenecorrect¬IGNO , with a ¬COLR 255 000 000hydrogen ¬COLR 000 000 000 assumed to be at every carbon. Each carbon on benzene is sp2 hybridized, and thus benzene is planar, or completely flat. The following picture gives an orbital representation of benzene with each carbon having a p orbital and 3 sp2 orbitals. Electrons are delocalized throughout the pi, or p orbital, system. ¬CIMG 000 120 benzeneorbital¬ LINE¬³ TRGT TEXT TITL Preperation¬ 00 LINE¬³ TEXT TITL Preparation of Benzene in Laboratory¬ 00 LINE¬³ TEXT IGNO 1. Bensoic acid with dry lime ¬LINE¬PLAN¬³ TEXT LINE¬³ RACT CMPD 030 000 R COOH¬ PLUS 050 025 CIMG 000 000 CaO¬ ARRW 050 050 025 NULL¬ NULL¬ CMPD 000 000 Benzene¬ PLUS 050 025 CIMG 000 030 CaCO3¬³ TEXT LINE¬³ TEXT IGNO 2. Using Sodalime ¬LINE¬³ RACT CMPD 060 000 R COONa¬ PLUS 050 025 CIMG 000 000 NaOH¬ ARRW 050 050 025 NULL¬ NULL¬ CMPD 000 000 Benzene¬ PLUS 050 025 CIMG 000 040 Na2CO3¬³ TEXT LINE¬ IGNO Here ¬COLR 255 000 000R=¬COLR 000 000 000¬ CIMG -01 000 C6H5¬LINE¬³ TEXT LINE¬³ TRGT TEXT TITL Reactions¬ 00 LINE¬³ TRGT TEXT TITL Additive Reactions¬ 00 LINE¬³ TRGT TEXT TITL Hydration¬ 00 LINE¬ IGNO Benzene react with Hydrogen under extreme conditions with catalyzers ¬ CIMG -02 000 Pt¬ CIMG 000 000 Pd¬ CIMG 000 002 Ni¬ IGNO This is due to the transitive double bonds which gives benzene the characteristic of Alkene .¬LINE¬³ RACT CMPD 070 000 Benzene Kekule¬ PLUS 050 025 CIMG 000 000 h2¬ ARRW 050 140 140 Pt¬ NULL¬ CMPD 000 030 cyclohexane¬³ TEXT LINE¬³ TRGT TEXT LINE¬ TITL Chlorion¬ 00 LINE¬ IGNO Reaction between Halogen and Alekene is an additive reaction. This is due to the transitive single bonds which gives benzene the characteristic of Alkane .¬LINE¬³ RACT CMPD 070 000 Benzene Kekule¬ PLUS 050 025 CIMG 000 000 cl2¬ ARRW 050 160 120 NULL¬ NULL¬ CMPD 000 050 hexaclorocyclohexane¬³ TRGT TEXT LINE¬ TITL Substitutional Reactions¬ 00 LINE¬ IGNO Following figures will show reactions to derive nitrobenzene,chlorobenzene and alkylebenzene.¬LINE¬LINE¬³ TRGT TEXT TITL Nitrification¬ 00 LINE¬³ RACT CMPD 040 000 benzene¬ ARRW 050 120 140 HNO3¬ H2SO4¬ CMPD -10 060 nitrophenyl¬³ TRGT TEXT LINE¬ TITL Alkylation¬ 00 LINE¬³ RACT CMPD 040 000 benzene¬ PLUS 050 025 CMPD 000 000 chloromethane¬ ARRW 050 140 100 AlCl3¬ NULL¬ CMPD -15 060 methylphenyl¬³ TEXT LINE¬LINE¬³ RACT CMPD 040 -30 benzene¬ PLUS 050 025 CMPD 000 030 RX¬ ARRW 050 140 100 AlCl3¬ NULL¬ CMPD -20 060 Rphenyl¬³ TRGT TEXT LINE¬ TITL Acylation¬ 00 LINE¬³ RACT CMPD 040 000 benzene¬ PLUS 050 025 CMPD 000 000 ch3cox¬ ARRW 050 140 100 AlCl3¬ NULL¬ CMPD -15 060 1-phenylethan-1-one¬³ TEXT LINE¬³ TRGT TEXT LINE¬ TITL Chlorion¬ 00 LINE¬³ RACT CMPD 040 000 benzene¬ PLUS 050 025 CIMG 000 000 cl2¬ ARRW 050 140 100 AlCl3¬ NULL¬ CMPD -15 060 chlorobenzene¬³ ENDP