Predict the major products formed when benzene reacts (just once) with the following reagents.
f. fuming sulfuric acid

Guida verificata passo dopo passo

Step 1: Recognize the reaction type. Benzene reacts with fuming sulfuric acid in an electrophilic aromatic substitution reaction, specifically sulfonation. Fuming sulfuric acid contains sulfur trioxide (SO₃) dissolved in concentrated sulfuric acid, which acts as the electrophile.

Step 2: Identify the electrophile. In this reaction, the electrophile is sulfur trioxide (SO₃), which reacts with benzene to form a sulfonic acid group (-SO₃H) attached to the benzene ring.

Step 3: Determine the mechanism. The reaction proceeds via the formation of a sigma complex (arenium ion) when the benzene ring donates π-electrons to the electrophile. This intermediate is stabilized by resonance.

Step 4: Regenerate aromaticity. The loss of a proton from the sigma complex restores the aromaticity of the benzene ring, resulting in the formation of benzene sulfonic acid.

Step 5: Predict the major product. Since the reaction occurs just once, the major product is benzene with a single sulfonic acid group (-SO₃H) attached to the ring. The position of substitution is typically at one of the carbons on the benzene ring, forming benzene sulfonic acid.

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Electrophilic Aromatic Substitution

Electrophilic aromatic substitution (EAS) is a fundamental reaction in organic chemistry where an electrophile replaces a hydrogen atom on an aromatic ring. In the case of benzene reacting with fuming sulfuric acid, the sulfur trioxide (SO3) generated acts as a strong electrophile, leading to the substitution of a hydrogen atom on the benzene ring.

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Sulfonation of Benzene

The sulfonation of benzene involves the introduction of a sulfonyl group (–SO3H) into the aromatic ring. When benzene reacts with fuming sulfuric acid, the major product formed is benzene sulfonic acid, which is a result of the electrophilic attack by the sulfur trioxide generated in the reaction. This process is reversible and can be reversed by hydrolysis.

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Reaction Conditions and Mechanism

The reaction conditions, such as the presence of fuming sulfuric acid, significantly influence the mechanism and outcome of the reaction. Fuming sulfuric acid provides a concentrated source of sulfur trioxide, enhancing the electrophilic character and facilitating the sulfonation process. Understanding the mechanism helps predict the major product and the conditions under which the reaction occurs.

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