Aromatic hydrocarbons: benzene reactions and side chain reactions

37 questions on Aromatic hydrocarbons: benzene reactions and side chain reactions from the Hydrocarbons chapter: 6 NEET level, 15 JEE Main, 16 JEE Advanced. Each one opens with its answer and solution.

• The electrophile in the nitration of benzene with a mixture of concentrated HNO3 and concentrated H2SO4 is NEET level
• Toluene is heated with hot alkaline KMnO4 and the mixture is then acidified. The product is NEET level
• Benzene reacts with excess chlorine in bright sunlight (no halogen carrier). The product is NEET level
• Toluene is treated with Cl2 in sunlight at its boiling point (no Lewis acid). The main monochlorinated product is JEE Main level
• tert-Butylbenzene is heated with hot alkaline KMnO4 and then acidified. The result (under the usual laboratory conditions) is JEE Main level
• Benzene is treated with 1-chloropropane and anhydrous AlCl3. The major product is JEE Main level
• Which of the following species is aromatic? JEE Main level
• Which is the correct order of reactivity towards electrophilic nitration? JEE Main level
• Which of the following compounds do NOT undergo Friedel-Crafts alkylation (with CH3Cl / anhydrous AlCl3) under the usual conditions? JEE Main level
• Which of the following are oxidised to benzoic acid by hot alkaline KMnO4 (followed by acidification)? JEE Main level
• Which sequence is the best route to m-nitrobenzoic acid from benzene? JEE Advanced level
• Ethylbenzene is treated with Cl2 in sunlight (1 mol, monochlorination at the side chain, major product), then with alcoholic KOH, and the resulting hydrocarbon ... JEE Advanced level
• o-, m- and p-Xylene (the three dimethylbenzenes) are each monochlorinated, ring and side-chain products both being counted (structural isomers only, no stereois... JEE Advanced level
• 1-Bromo-4-methylbenzene is nitrated with a mixture of concentrated HNO3 and H2SO4 at low temperature. The major mononitro product is JEE Advanced level
• Which sequence gives n-propylbenzene as the major product from benzene? JEE Advanced level
• Toluene is heated with 3 mol of Cl2 in sunlight, giving a trichloro compound. This is boiled with aqueous NaOH and then acidified. The final organic product is JEE Advanced level
• A mixture of bromobenzene, 1-bromo-4-methylbenzene and bromomethane (all in equal amount) is treated with sodium metal in dry ether. Assuming every possible cou... JEE Advanced level
• Cumene is manufactured from benzene and propene, and then converted into phenol by the cumene process. Select the correct statement(s). JEE Advanced level
• Treating each species as fully conjugated, cyclic and planar when that is geometrically possible, which of the following are aromatic according to Huckel's rule... JEE Advanced level
• Nitration of toluene with a mixture of conc. HNO3 and conc. H2SO4 gives mainly: NEET level
• Which of the following species is aromatic according to Huckel's rule? NEET level
• Toluene on heating with alkaline KMnO4 followed by acidification gives: NEET level
• Toluene is treated with excess chlorine in sunlight at its boiling point, and the product is hydrolysed with hot aqueous alkali followed by acidification. The f... JEE Main level
• Which of the following does NOT undergo Friedel-Crafts alkylation with CH3Cl and anhydrous AlCl3? JEE Main level
• Benzene reacts with 1-chloropropane in the presence of anhydrous AlCl3. The major product is: JEE Main level
• The correct order of reactivity towards electrophilic aromatic substitution is: JEE Main level
• In the nitration of benzene with the mixed acid, the slowest (rate-determining) step is: JEE Main level
• Which of the following electrophilic substitutions of benzene is reversible? JEE Main level
• Which of the following substituents on a benzene ring are meta directing? JEE Main level
• Which of the following, on vigorous oxidation with hot alkaline KMnO4 followed by acidification, give benzoic acid? JEE Main level
• Which reagent sequence converts benzene into 1-bromo-3-nitrobenzene most efficiently? JEE Advanced level
• The most efficient route from toluene to 3-nitrobenzoic acid is: JEE Advanced level
• To prepare n-butylbenzene from benzene without rearrangement, the best method is: JEE Advanced level
• Ethylbenzene is heated with Br2 under light to give X (major). X is heated with alcoholic KOH to give Y. Y is treated with HBr in the presence of an organic per... JEE Advanced level
• Which of the following methods can be used to prepare ethylbenzene from benzene or bromobenzene? JEE Advanced level
• Which of the following species are aromatic (planar, cyclic, fully conjugated, (4n+2) pi electrons)? JEE Advanced level
• Which of the following, on side-chain monochlorination with Cl2/light (no ring substitution), give only one constitutional isomer of the monochloro product? JEE Advanced level