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.

Show the resonance forms for the enolate ions that result when the following compounds are treated with a strong base.

(a) ethyl acetoacetate

(b) pentane-2,4-dione

When cis-2,4-dimethylcyclohexanone is dissolved in aqueous ethanol containing a trace of NaOH, a mixture of cis and trans isomers results. Propose a mechanism for this isomerization.

For each molecule shown below,

1. indicate the most acidic hydrogens.

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

(d)

For each molecule shown below,

1. indicate the most acidic hydrogens.

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

(e)

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.

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.