(Originais Teachy 2023) - Question Medium of Chemistry

When performing an electrophilic aromatic substitution reaction (SEAr) with phenol (C6H5OH), a common substance that can be used as a reagent is bromine (Br2) in acidic solution. This reaction occurs with phenols in general due to the high electron density of the benzene ring, thus attracting the bromonium cation (Br+). The main product is 2-bromophenol. Considering the presented context, describe the detailed mechanism of the SEAr reaction of phenol with bromine, including all intermediate steps and intermediates formed. Explain how the high electron density of the benzene ring of phenol influences the formation of the product 2-bromophenol. Additionally, briefly discuss which factors may influence the selectivity for the formation of 2-bromophenol instead of other possible isomers. Respond in a clear and well-structured text, demonstrating knowledge about the properties and reactivity of phenols in SEAr reactions.