Following is a two-part question based on the nucleophilic aromatic substitution reaction below, which converts chlorobenzene to phenol. OH .CI NaOH, heat H20 Considering that this reaction goes through an elimination and addition mechanism, which reactive intermediate below is formed during the reaction? OH OH CI CI Choose one: Please do NOT use wedges or dashes in this question. A graduate student wanted to perform this nucleophilic aromatic substitution, however the student added cyclopentadiene as a solvent. Phenol was not formed. What was formed instead? .CI NaOH, heat Draw the product:

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Aromatic Compounds

Aromatic organic compound or aromatic system is an important class of hydrocarbons under the branch of organic chemistry. Aromatic compounds are also called arenas. The definition of aromatic organic compounds can be stated as a class of organic compounds with a planar cyclic ring of atoms bonded through alternated single and double bonds. Due to these alternating bonds, a peculiar feature termed as ‘resonance’, that is, delocalization of pi electrons or the electrons is shared within the atoms of the ring which are present in the aromatic compounds. The word ‘aromatic’ includes a Greek word ‘aroma’ which means smell, indicating that they were named as such due to the sweet odor they produce. Many well-known flavors such as vanilla, cinnamon, and few scents from flowers are extracted from aromatic compounds. Benzene with chemical formula C6H6 is a very common aromatic compound that contains six atoms of carbon held in the cyclic ring of alternate double bonds. It is also to be noted that not all aromatic compounds contain benzene ring. This can be explained by Huckel’s rule.