How do you convert the following?

• (A) Phenol to anisole
• (B) Propan-2-ol to 2-methylpropan-2-ol
• (C) Aniline to phenol

Converting organic compounds involves specific reactions that transform one molecule into another. Let's break down each of your conversions step by step, focusing on the mechanisms and reagents involved.

Transforming Phenol to Anisole

To convert phenol (C6H5OH) to anisole (C6H5OCH3), you can use a method called methylation. The most common reagent for this transformation is methyl iodide (CH3I) in the presence of a base, such as sodium hydroxide (NaOH).

Steps Involved:

• Deprotonation: First, the hydroxyl group of phenol is deprotonated by the base, forming the phenoxide ion (C6H5O^-).
• Nucleophilic Attack: The phenoxide ion acts as a nucleophile and attacks the electrophilic carbon in methyl iodide, resulting in the formation of anisole and iodide ion (I^-).

This reaction is efficient due to the good leaving group ability of iodide and the strong nucleophilicity of the phenoxide ion.

Converting Propan-2-ol to 2-Methylpropan-2-ol

To achieve this conversion, you can use a process called dehydration followed by rearrangement. Propan-2-ol (C3H8O) can be converted to 2-methylpropan-2-ol (C5H12O) through an acid-catalyzed reaction.

Procedure:

• Dehydration: Heat propan-2-ol with an acid catalyst, such as sulfuric acid (H2SO4). This will lead to the formation of an alkene (propene) by removing a water molecule.
• Rearrangement: The formed propene can then undergo a hydride shift to form a more stable tertiary carbocation, which can then react with water to yield 2-methylpropan-2-ol.

This method effectively increases the carbon skeleton while maintaining the alcohol functional group.

Transforming Aniline to Phenol

The conversion of aniline (C6H5NH2) to phenol (C6H5OH) can be achieved through a process called hydrolysis of the aniline derivative. A common approach is to first convert aniline to its diazonium salt and then hydrolyze it.

Steps to Follow:

• Diazotization: Treat aniline with nitrous acid (generated in situ from sodium nitrite and hydrochloric acid) to form benzene diazonium chloride (C6H5N2Cl).
• Hydrolysis: The diazonium salt can then be treated with water or a dilute acid, which will replace the diazonium group with a hydroxyl group, yielding phenol.

This method is particularly useful because it allows for the selective transformation of an amine to a phenolic compound while avoiding side reactions.

In summary, each of these conversions utilizes specific reagents and conditions to achieve the desired transformations. Understanding the underlying mechanisms helps in predicting the outcomes and optimizing the reactions for better yields.