For each of the following reagents, decide whether chlorobenzene will react with it or not, and, if it does, draw and name the products expected from the reaction.
c. HNO₃ and H₂SO₄ catalyst

검증된 단계별 안내

Step 1: Recognize the type of reaction. Chlorobenzene is an aromatic compound, and the combination of HNO3 (nitric acid) and H2SO4 (sulfuric acid) is a common reagent pair used for nitration reactions. Nitration is an electrophilic aromatic substitution reaction where a nitro group (-NO2) is introduced to the benzene ring.

Step 2: Understand the role of the reagents. H2SO4 acts as a catalyst and protonates HNO3, generating the nitronium ion (NO2⁺), which is the electrophile in this reaction. The reaction mechanism involves the formation of this reactive species.

Step 3: Determine the reactivity of chlorobenzene. The chlorine atom on chlorobenzene is an electron-withdrawing group due to its inductive effect, but it also has a resonance-donating effect. This makes chlorobenzene less reactive than benzene but still capable of undergoing electrophilic aromatic substitution. The resonance effect directs the incoming electrophile to the ortho and para positions relative to the chlorine atom.

Step 4: Predict the products. When chlorobenzene reacts with the nitronium ion, the nitro group (-NO2) will substitute at the ortho and para positions. The major product is typically the para-substituted product due to steric hindrance at the ortho position. The products are 1-chloro-4-nitrobenzene (para product) and 1-chloro-2-nitrobenzene (ortho product).

Step 5: Name the products. The para product is named 1-chloro-4-nitrobenzene, and the ortho product is named 1-chloro-2-nitrobenzene. These are the expected products of the nitration of chlorobenzene using HNO3 and H2SO4.

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주요 개념

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Electrophilic Aromatic Substitution

Electrophilic aromatic substitution (EAS) is a fundamental reaction mechanism in organic chemistry where an electrophile replaces a hydrogen atom on an aromatic ring. In the case of chlorobenzene, the presence of the chlorine atom, which is a deactivating group, influences the reactivity and orientation of the substitution. Understanding EAS is crucial for predicting how chlorobenzene will react with reagents like nitric acid and sulfuric acid.

Nitration of Aromatic Compounds

Nitration is a specific type of electrophilic aromatic substitution where a nitro group (NO2) is introduced into an aromatic compound. This reaction typically requires a mixture of concentrated nitric acid (HNO3) and sulfuric acid (H2SO4) to generate the nitronium ion (NO2+), the active electrophile. Recognizing the conditions and products of nitration is essential for determining the outcome of chlorobenzene's reaction with these reagents.

Reactivity of Chlorobenzene

Chlorobenzene is less reactive than other aromatic compounds due to the electron-withdrawing nature of the chlorine atom, which stabilizes the aromatic system and makes it less susceptible to electrophilic attack. This reactivity is important to consider when predicting whether chlorobenzene will react with nitrating agents. Understanding the influence of substituents on aromatic reactivity helps in anticipating the products formed during the reaction.

For each of the following reagents, decide whether chlorobenzene will react with it or not, and, if it does, draw and name the products expected from the reaction.c. HNO3 and H2SO4 catalyst