(Solved):   1. Phenolic compounds are often used as free-radical inhibitors. They are added in small a ...

 

1. Phenolic compounds are often used as free-radical inhibitors. They are added in small amounts to the monomer to prevent free-radical polymerization when the monomer is in transit or sitting on the shelf. These inhibitors must be removed prior to doing any free-radical chemistry. This is typically done by treating the monomer with aqueous base. For the following reaction, on which side does the equilibrium lie? Using curved arrows to show electron movement, give the mechanism for this reaction as it proceeds from left to right. Comment on the water solubility of sodium phenoxide. 2. For the previous acid base process, both hydroxide and phenoxide feature a negative charge on oxygen. Which is more stable with the negative charge -hydroxide or phenoxide? Explain. 3. When benzoyl peroxide is heated, carbon dioxide is formed as well as biphenyl by a free-radical \( \mid \) coupling process. Use single electron (fishhook) arrows for each step in the given mechanism to show the formation of biphenyl. benzoyl peroxide biphenyl Mechanism step 1 \( \underline{\underline{s t e p}} \underline{\underline{2}} \)