Acetylacetone (pentane-2,4-dione) reacts with sodium hydroxide to give water and the sodium salt of a carbanion. Write a complete structural formula for the carbanion, and use resonance forms to show the stabilization of the carbanion.

Choose the more basic member of each pair of isomers, and show why the base you chose is more basic.

e.

The following compounds can all react as bases.

b. Rank the conjugate acids in the order you would predict, from most stable to least stable.

Four pairs of compounds are shown. In each pair, one of the compounds reacts more quickly, or with a more favorable equilibrium constant, than the less conjugated system. In each case, explain the enhanced reactivity.

(d)

Use resonance forms of the conjugate bases to explain why methanesulfonic acid (CH₃SO₃H, pK_a = –2.6) is a much stronger acid than acetic acid (CH₃COOH, pK_a = 4.8).

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

(a)

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

(c)

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

(a)

Without using pK_a values, pick out the least reactive (most stable) base in each pair. Explain your answer.

(a)