Which one of the following gives only one mononitro product (constitutional isomer) on nitration of the ring?

A1,3-dimethylbenzene (m-xylene)
B1,4-dimethylbenzene (p-xylene)
Cmethylbenzene (toluene)
D1,2-dimethylbenzene (o-xylene)

Answer: B

In p-xylene all four ring hydrogens are equivalent, so there is only one mononitro product. Toluene gives ortho, meta and para isomers, o-xylene gives 2 (3-nitro and 4-nitro) and m-xylene gives 3 (2-nitro, 4-nitro, 5-nitro).

Practice Organic Reaction Mechanisms II: Electrophilic and Radical Reactions More on Electrophilic aromatic substitution: mechanism and directing effects

Previous questionNext question

More questions on Electrophilic aromatic substitution: mechanism and directing effects

Acetanilide (C6H5NHCOCH3) is nitrated with HNO3 in H2SO4 at low temperature. The major product is JEE Main level
Assertion (A): Nitrobenzene does not undergo Friedel-Crafts reaction. Reason (R): The -NO2 group strongly deactivates the benzene ring towar... JEE Main level
p-CH3-C6H4-OCH3 (4-methylanisole) is nitrated under mild conditions with dilute HNO3. The major mononitration product is JEE Main level
Which sequence of reactions converts benzene mainly into 1-bromo-3-nitrobenzene? JEE Main level
Benzene is treated successively with (i) CH3CH2CH2COCl, anhydrous AlCl3 and (ii) Zn(Hg), conc. HCl. The final product is JEE Main level
Consider the following ring substituents on benzene: -F, -Cl, -OH, -NHCOCH3, -NO2, -CN, -Br, -CH3, -COOH, -I. Count how many of them are bot... JEE Main level