In a theoretical organic chemistry experiment, a compound "D" with a molecular formula $\mathrm{C}_{7} \mathrm{H}_{8} \mathrm{O}_{2}$ is reacted with sodium metal to produce a compound "E" $\left(\mathrm{C}_{7} \mathrm{H}_{7} \mathrm{ONa}\right)$ and hydrogen gas. Further, when " $\mathrm{E}$ " is treated with dilute hydrochloric acid ( $\mathrm{HCl}$ ), it regenerates compound "D". Additionally, "D" undergoes an esterification reaction with methanol in the presence of sulfuric acid to form an ester " $\mathrm{F}^{\prime \prime}\left(\mathrm{C}_{8} \mathrm{H}_{10} \mathrm{O}_{3}\right)$. Identify the structures of compounds D, E, and F, and explain the type of chemical reactions involved in each transformation.

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∻Solution∻ ‖ 1 ⋮ **Identify the reaction with sodium metal**: The compound "D" with molecular formula $ \mathrm{C}_{7} \mathrm{H}_{8} \mathrm{O}_{2} $ reacts with sodium metal to produce compound "E" $ \left( \mathrm{C}_{7} \mathrm{H}_{7} \mathrm{ONa} \right) $ and hydrogen gas. This indicates that "D" is likely a phenol derivative, as phenols react with sodium to form phenoxide salts and hydrogen gas. ‖ ‖ 2 ⋮ **Reaction with dilute hydrochloric acid**: When compound "E" is treated with dilute hydrochloric acid ( $ \mathrm{HCl} $ ), it regenerates compound "D". This confirms that "E" is the sodium salt of "D", and "D" is a phenol derivative. ‖ ‖ 3 ⋮ **Esterification reaction**: Compound "D" undergoes an esterification reaction with methanol in the presence of sulfuric acid to form an ester " $ \mathrm{F}^{\prime \prime} \left( \mathrm{C}_{8} \mathrm{H}_{10} \mathrm{O}_{3} \right) $. This suggests that "D" has a carboxyl group that reacts with methanol to form the ester. ‖ ‖ 4 ⋮ **Determine the structure of "D"**: Given the molecular formula $ \mathrm{C}_{7} \mathrm{H}_{8} \mathrm{O}_{2} $ and the reactions described, "D" is likely 4-hydroxybenzoic acid. This compound has both a hydroxyl group (phenol) and a carboxyl group. ‖ ‖ 5 ⋮ **Determine the structure of "E"**: Compound "E" is the sodium salt of 4-hydroxybenzoic acid, which is sodium 4-hydroxybenzoate. ‖ ‖ 6 ⋮ **Determine the structure of "F"**: The ester " $ \mathrm{F}^{\prime \prime} $ " formed from the esterification of 4-hydroxybenzoic acid with methanol is methyl 4-hydroxybenzoate. ‖ ∻Answer∻ ⚹ Compound "D" is 4-hydroxybenzoic acid ( $ \mathrm{C}_{7} \mathrm{H}_{8} \mathrm{O}_{2} $ ). Compound "E" is sodium 4-hydroxybenzoate ( $ \mathrm{C}_{7} \mathrm{H}_{7} \mathrm{ONa} $ ). Compound "F" is methyl 4-hydroxybenzoate ( $ \mathrm{C}_{8} \mathrm{H}_{10} \mathrm{O}_{3} $ ). ⚹ ∻Key Concept∻ ⚹ Identification of organic compounds based on their reactions ⚹ ∻Explanation∻ ⚹ The identification of compounds "D", "E", and "F" is based on their chemical reactions: reaction with sodium metal, reaction with hydrochloric acid, and esterification with methanol. These reactions help determine the functional groups present in the compounds. ⚹◊What type of chemical reaction occurs when compound "D" undergoes esterification with methanol in the presence of sulfuric acid to form compound "F⍭ Generate me a similar question◊

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