determine which base will work to deprotonate each compound in an acid/base extraction.\nchoose...\nhydroxide…

Explanation:

Step1: Recall acid - base reactivity

The acidity of a compound determines which base can deprotonate it. Carboxylic acids are more acidic than phenols, and alcohols are the least acidic among common organic compounds.

Step2: Analyze the first compound (benzoic - like acid)

The first compound has a carboxylic acid group. Carboxylic acids ($pK_a \approx 4 - 5$) can be deprotonated by both hydroxide ($OH^-$) and bicarbonate ($HCO_3^-$) since the conjugate base of bicarbonate ($CO_3^{2 - }$) has a $pK_a$ of about 10. Answer: Hydroxide or bicarbonate

Step3: Analyze the second compound (phenol - like)

Phenols ($pK_a \approx 10$) can be deprotonated by hydroxide but not by bicarbonate because bicarbonate is not a strong enough base to deprotonate phenol. Answer: Only hydroxide

Step4: Analyze the third compound (alcohol - like)

Alcohols ($pK_a \approx 16 - 18$) are too weak acids to be deprotonated by either hydroxide or bicarbonate under normal conditions in acid - base extractions. Answer: Neither hydroxide nor bicarbonate