Benzoic acid and phenol are insoluble in water. When sodium bicarbonate is added to the water, benzoic acid dissolves, but phenol does not. The addition of sodium hydroxide causes both to dissolve. On the basis of these observations, estimate the pK_a of phenol. [The pK_a of H₂CO₃ is 6.4.]

For each of the following molecules, predict the product that would form upon reaction of a single equivalent of a strong base.

(c)

Identify the stronger base in each pair. Explain your choice. Citing pK_a values is not an acceptable answer.

(d)

For each of the following molecules, predict the product that would form upon reaction of a single equivalent of a strong base.

(a)

Identify the stronger acid in each pair. Explain your choice. Citing pK_a values is not an acceptable answer.

(a)

For each of the following molecules, predict the product that would form upon reaction of a single equivalent of a strong base.

(b)

Identify the stronger base in each pair. Explain your choice. Citing pK_a values is not an acceptable answer.

(c)