Reactions of Benzene: Making the Unreactive React
Benzene's stability creates a problem - it's too stable to react easily! However, chemists have developed clever ways to make it react through electrophilic substitution rather than addition reactions that would destroy the stable ring.
Friedel-Crafts acylation uses a halogen carrier catalyst like AlCl₃ to create a powerful electrophile. The catalyst polarises an acyl chloride (RCOCl), forming a carbocation that's strong enough to attack benzene's electron-rich ring. Under reflux with dry ether, this produces phenylketones.
The reaction mechanism involves the delocalised electrons attacking the electrophile, temporarily breaking the ring's stability. A hydrogen is then removed, reforming the aromatic ring with the new acyl group attached.
Exam Tip: Remember that benzene undergoes substitution, not addition - this preserves the stable aromatic ring structure.
Nitration of benzene creates nitrobenzene, essential for making explosives and dyes. Concentrated nitric and sulfuric acids react to form the nitronium ion (NO₂⁺), a powerful electrophile. Keep temperatures below 55°C to avoid multiple substitutions - too hot and you'll get unwanted products!