Asked in ETEA MDCAT 2014 2014Moderate

Which of the following compounds undergo nitration most readily?

Correct answer: B. Toluene

  • A. Benzene
  • B. Toluene
  • C. Benzoic acid
  • D. Nitrobenzene

Explanation

The correct answer is Toluene. Toluene undergoes nitration much faster than benzene due to the presence of a methyl group. This group donates electron density to the ring, particularly enhancing the reactivity at the ortho and para positions, making the electrophilic aromatic substitution process more favorable.Why the other options are incorrect:Benzene: While benzene can undergo nitration, it lacks activating groups, making it less reactive compared to toluene.Benzoic Acid: The carboxyl group is a deactivating group, reducing electron density in the ring and hindering electrophilic attack.Nitrobenzene: The nitro group is a strong deactivator, making further nitration extremely difficult due to the electron-deficient ring.

Last updated

About Benzene and Aromatic Compounds

Benzene has a planar ring of delocalised π electrons, giving aromatic stability and equal carbon-carbon bond lengths. The topic covers resonance, electrophilic substitution reactions such as nitration, halogenation, sulphonation and Friedel-Crafts reactions, along with substituent effects and the distinction between substitution in benzene and addition in ordinary alkenes.

Practise Chemistry of Hydrocarbons

1,091 free Chemistry of Hydrocarbons MCQs from Chemistry, each with the correct answer and an explanation. Unlimited attempts, no account needed.

Exams that ask Chemistry questions like this

Chemistry is on 12 papers prepared for on TestUstad, and all of them draw the same bank, so this question is worth knowing for every one of them.

Related questions