We can prepare benzene by 3C2H2 → C6H6 over red hot Fe (873K) – three rotis making a full thali, or by benzoate + soda lime → benzene like removing a mango seed, and phenol + Zn dust → benzene like scrubbing with a cleaner.
Benzene prefers electrophilic substitution — its rich pi-cloud happily attacks an electrophile to form a sigma complex, then H+ leaves, keeping aromaticity intact. Important examples: Nitration (HNO3/H2SO4 → C6H5-NO2), Halogenation (Cl2/FeCl3 → C6H5-Cl), Sulphonation (H2SO4 → C6H5-SO3H), Friedel-Crafts alkylation (RCl/AlCl3 → C6H5-R) and acylation (RCOCl/AlCl3 → C6H5-COR).
Groups show directive effect: o,p-directing activating groups like -OH, -NH2, -CH3, -OCH3 are generous mummies pushing electrons to ortho-para; m-directing deactivating groups like -NO2, -COOH, -CHO, -CN, -SO3H are strict principals pulling electrons and directing to meta. Polycyclic aromatic hydrocarbons (PAH) with >2 rings like naphthalene are carcinogenic, like the smoke from burnt roti.
Revision: Prep: 3C2H2 → C6H6 (red hot Fe) (3 rotis→thali), benzoate+soda lime (mango seed), phenol+Zn (scrub). Electrophilic substitution – pi → E+ → sigma complex → H+ leaves, aromaticity retains. Nitration, Halogenation, Sulphonation, Friedel-Crafts alkylation/acylation. o,p activating (OH, NH2, CH3, OCH3 generous Mummy), m deactivating (NO2, COOH, CHO, CN, SO3H strict Principal). PAH carcinogenic >2 rings (naphthalene, burnt roti smoke).
Quick Revision Box
- Prep 3C2H2 red hot Fe to C6H6 benzoate+soda lime phenol+Zn, Electrophilic substitution pi to E+ sigma H+ leaves, Nitration Halogenation Sulphonation Friedel-Crafts, o,p activating OH NH2 CH3 OCH3 generous Mummy ortho para m deactivating NO2 COOH CHO CN strict Principal meta PAH carcinogenic