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Medical College Admission Test
Chemical and Physical Foundations of Biological Systems

Reactivity of Toluene in Electrophilic Aromatic Substitution

Hard Organic Chemistry Aromatic Compounds

Aromatic compounds are a significant class in organic chemistry, characterized by their stability and unique chemical properties due to delocalized pi electrons. Among various aromatic compounds, there is a particular interest in the substitution reactions involving electrophiles. An example of an aromatic compound is toluene (C7H8), which is derived from benzene by the substitution of a hydrogen atom with a methyl group. Understanding the reactivity of toluene as compared to benzene is crucial for predicting the behavior of electrophilic aromatic substitution reactions.

Given this context, consider the following statements regarding the reactivity and stability of toluene in electrophilic aromatic substitution:

  1. Toluene is more reactive than benzene in electrophilic substitution reactions due to the electron-donating effect of the methyl group.
  2. In electrophilic aromatic substitution, toluene tends to undergo substitution at the ortho and para positions with respect to the methyl group more frequently than at the meta position.
  3. The methyl group in toluene can stabilize adjacent positive charges developed during the intermediates of electrophilic substitution.
  4. The introduction of an electrophile into the toluene structure generally occurs more rapidly than into a non-aromatic compound with similar reactivity profiles.

Hint

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Correct11.0K
% Correct76%