Alkylation of the following compound with methyl iodide under two different conditions forms two different ketoesters (A and B). Each ketoester forms a cyclic diketone (C and D) when treated with methoxide ion in methanol. a. Draw the structures of A and B, and indicate the conditions used in the alkylation reaction that cause that ketoester to be formed.

Phenylacetone can form two different enols.

(a) Show the structures of these enols.

(b) Predict which enol will be present in the larger concentration at equilibrium.

For each molecule shown below,

1. indicate the most acidic hydrogens.

(a)

(b)

(c)

Draw the products of the following reactions:

b.

Draw the products of the following reactions:

a.

2. Indicate which compounds would be more than 99% deprotonated by a solution of sodium ethoxide in ethanol.

For each molecule shown below,

2. draw the important resonance contributors of the anion that results from removal of the most acidic hydrogen.

(a)

(b)

(c)

1. Rank the following compounds in order of increasing acidity.

Give the important resonance forms for the possible enolate ions of the following:

(a) acetone

(b) cyclopentanone