Show how you would convert aniline to the following compounds.
(g) phenol

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Step 1: Begin with aniline (C6H5NH2) as the starting material. Protect the amino group by converting it into an acetamide group. This can be achieved by reacting aniline with acetic anhydride (CH3CO)2O. The product will be acetanilide (C6H5NHCOCH3). This step prevents unwanted reactions at the amino group during subsequent steps.

Step 2: Perform a diazotization reaction to convert the protected aniline into a diazonium salt. React acetanilide with sodium nitrite (NaNO2) and hydrochloric acid (HCl) at low temperatures (0–5°C). This forms the diazonium salt intermediate.

Step 3: Hydrolyze the acetamide group back to the amino group by treating the diazonium salt with water and heat. This step regenerates the free amino group while maintaining the diazonium functionality.

Step 4: Replace the diazonium group (-N2+) with a hydroxyl group (-OH) by performing a Sandmeyer reaction. Treat the diazonium salt with water and copper salts (Cu2+), which facilitates the substitution of the diazonium group with a hydroxyl group, yielding phenol (C6H5OH).

Step 5: If the target compound is 3-methylphenol, ensure that the methyl group is introduced at the correct position on the benzene ring. This can be achieved by starting with 3-methylaniline and following the same sequence of reactions: protection, diazotization, hydrolysis, and Sandmeyer reaction.

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Key Concepts

Here are the essential concepts you must grasp in order to answer the question correctly.

Aniline and its Derivatives

Aniline is an aromatic amine with the formula C6H5NH2. It serves as a precursor for various chemical transformations. Understanding the structure and reactivity of aniline and its derivatives, such as 3-methylaniline, is crucial for predicting how they can be converted into other compounds, like phenol.

Electrophilic Aromatic Substitution (EAS)

Electrophilic aromatic substitution is a fundamental reaction in organic chemistry where an electrophile replaces a hydrogen atom on an aromatic ring. This mechanism is essential for converting aniline derivatives into phenolic compounds, as it allows for the introduction of functional groups while preserving the aromatic system.

Oxidation Reactions

Oxidation reactions involve the loss of electrons or an increase in oxidation state, often resulting in the formation of alcohols, ketones, or aldehydes. In the context of converting aniline to phenol, understanding the specific oxidation conditions and reagents that facilitate this transformation is vital for successful synthesis.

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