Question

according to figure 2, which compound would be extracted if we treat our mixture with hcl, separate the layers; treat the organic layer with sodium bicarbonate and separate the new layers and treat the aqueous bicarbonate layer with hcl
askcuddy
correct answer:
the answer is benzoic acid.
explanation:
benzocaine
phenol
naphthalene
benzoic acid
benzoic acid and naphthalene

Explanation:

When treating the mixture with HCl, basic compounds (like benzocaine, which has an amine group) react and go to the aqueous layer. After separating, treating the organic layer (which now has acidic compounds like benzoic acid and phenol, and neutral naphthalene) with sodium bicarbonate. Benzoic acid (a stronger acid than phenol in terms of reaction with bicarbonate) reacts with sodium bicarbonate to form a water - soluble salt and goes to the aqueous bicarbonate layer. Then treating the aqueous bicarbonate layer with HCl regenerates benzoic acid (since HCl is a stronger acid and can protonate the benzoate ion). Phenol does not react with sodium bicarbonate under normal conditions (as it is a weaker acid compared to the acid formed from bicarbonate decomposition equilibrium). Naphthalene is neutral and does not react with either HCl or sodium bicarbonate in the way described.

Answer:

benzoic acid