Show how the following products might be synthesized from suitable Michael donors and acceptors.

(c)

Show how the following products might be synthesized from suitable Michael donors and acceptors.

(d)

Show how the following products might be synthesized from suitable Michael donors and acceptors.

(e)

Show how the following products might be synthesized from suitable Michael donors and acceptors.

(f)

Propose a mechanism for the following reaction.

The base-catalyzed reaction of an aldehyde (having no α hydrogens) with an anhydride is called the Perkin condensation. Propose a mechanism for the following example of the Perkin condensation. (Sodium acetate serves as the base.)

Show how you would use Robinson annulations to synthesize the following compounds. Work backward, remembering that the cyclohexenone is the new ring and that the double bond of the cyclohexenone is formed by the aldol with dehydration. Take apart the double bond, then see what structures the Michael donor and acceptor must have.

(a)

Show how you would use Robinson annulations to synthesize the following compounds. Work backward, remembering that the cyclohexenone is the new ring and that the double bond of the cyclohexenone is formed by the aldol with dehydration. Take apart the double bond, then see what structures the Michael donor and acceptor must have.

(b)

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)

For each molecule shown below,

1. indicate the most acidic hydrogens.

(a)

(b)

(c)

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.

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

(g)

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.

(h)

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

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

Predict the products of the following aldol condensations. Show the products both before and after dehydration.

(a)

Predict the products of the following aldol condensations. Show the products both before and after dehydration.

(b)

Predict the products of the following aldol condensations. Show the products both before and after dehydration.

(c)

Predict the products of the following aldol condensations. Show the products both before and after dehydration.

(d)

Predict the products of the following aldol condensations. Show the products both before and after dehydration.

(e)

Predict the products of the following aldol condensations. Show the products both before and after dehydration.

(f)

Predict the products of the following Claisen condensations.

(a)

(b)

Predict the products of the following Claisen condensations.

(c)

Predict the products of the following Claisen condensations.

(d)

Predict the products of the following Claisen condensations.

(e)

Propose mechanisms for the reactions shown in Problems 22-62 part (a).

Propose mechanisms for the reactions shown in Problems 22-63 part (a).

Propose mechanisms for the reactions shown in Problems 22-63 part (b).

Pentane-2,4-dione (acetylacetone) exists as a tautomeric mixture of 8% keto and 92% enol forms. Draw the stable enol tautomer, and explain its unusual stability.