Question

determine which base will work to deprotonate each compound in an acid/base extraction.

Explanation:

Step1: Analyze first compound

The first compound is a benzoic - acid derivative. Benzoic acids are relatively strong acids among organic acids. A common base for deprotonating them in acid - base extraction is sodium bicarbonate ($\mathrm{NaHCO_3}$) as it can react with the carboxylic acid group ($\mathrm{-COOH}$) to form a water - soluble carboxylate salt.

Step2: Analyze second compound

The second compound is a phenol derivative. Phenols are less acidic than carboxylic acids. A stronger base like sodium hydroxide ($\mathrm{NaOH}$) is required to deprotonate the phenol group ($\mathrm{-OH}$) on the aromatic ring to form a phenoxide ion.

Step3: Analyze third compound

The third compound is an alcohol. Alcohols are even less acidic than phenols. A very strong base such as sodium hydride ($\mathrm{NaH}$) is needed to deprotonate the alcohol group ($\mathrm{-OH}$) to form an alkoxide ion.

Answer:

1. Sodium bicarbonate ($\mathrm{NaHCO_3}$)
2. Sodium hydroxide ($\mathrm{NaOH}$)
3. Sodium hydride ($\mathrm{NaH}$)