Question

determine which base will work to deprotonate each compound in an acid/base extraction.
choose...
hydroxide or bicarbonate
only bicarbonate
neither hydroxide nor bicarbonate
only hydroxide
choose...
choose...

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.