Question

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

Explanation:

Step1: Analyze first compound

The first compound has a carboxylic - acid group. Carboxylic acids are relatively strong organic acids. A weak base like sodium bicarbonate ($\mathrm{NaHCO_3}$) can deprotonate it as the pKa of carboxylic acids is around 4 - 5 and the pKa of $\mathrm{H_2CO_3}$ (from $\mathrm{NaHCO_3}$) is around 6.35.

Step2: Analyze second compound

The second compound has a phenol group. Phenols have a pKa around 10. A stronger base like sodium hydroxide ($\mathrm{NaOH}$) is needed to deprotonate phenols since they are less acidic than carboxylic acids.

Step3: Analyze third compound

The third compound has an alcohol group. Alcohols are very weak acids (pKa around 16 - 18). A very strong base such as sodium hydride ($\mathrm{NaH}$) is required to deprotonate them.

Answer:

For the first compound (carboxylic - acid containing): Sodium bicarbonate ($\mathrm{NaHCO_3}$)
For the second compound (phenol - containing): Sodium hydroxide ($\mathrm{NaOH}$)
For the third compound (alcohol - containing): Sodium hydride ($\mathrm{NaH}$)