Benzene Reactions Practice Problems

Draw and name the three possible substitution products formed when aniline reacts with Br₂/FeBr₃.

Aromatic compounds can be hydrogenated at high temperatures and pressures. Draw the structure of the alkane product formed when three molecules of H₂ are added to p-xylene in the presence of Rh catalyst at 1000 psi and 100°C.

Picric acid or trinitrophenol (TNP) is widely used in explosives and munitions. Picric is formed from phenol. To avoid side reactions, phenol is first sulfonated to form p-hydroxybenzenesulfonic acid. This is followed by successive nitration. The sulfonic acid group is then displaced by heating in dilute sulfuric acid and final nitration to produce the desired product, picric acid. Considering that nitration only occurs in the ortho and para positions relative to the hydroxy group, predict the structure of picric acid.

Phenols undergo aromatic substitution reactions. Write the chemical equation when p-nitrophenol reacts with Cl₂. Note that this reaction will form two substitution products.

Styrene is used as a precursor to produce rubbers and plastics. Its structure is shown below.

Predict the major product formed from the reaction of styrene with water and sulfuric acid catalyst.