Draw the products of the following reactions:

a.

Draw the products of the following reactions:

b.

Which of the following esters cannot undergo a Claisen condensation?

Show how each of the following compounds can be prepared from methyl phenyl ketone:

c.

Write the mechanism for the reaction of a 1,7-diester with an alkoxide ion to form a cyclic b-keto ester.

Can 2,4-pentanedione undergo an intramolecular aldol addition? If so, why? If not, why not?

Draw the product of the reaction of each of the following compounds with a base:

a.

Draw the product of the reaction of each of the following compounds with a base:

b.

Draw the product of the reaction of each of the following compounds with a base:

c.

Draw the product of the reaction of each of the following compounds with a base:

d.

Draw the product obtained by heating each pair of ketones in a basic solution.

a.

Draw the product obtained by heating each pair of ketones in a basic solution.

b.

What two carbonyl compounds are needed to synthesize each of the following compounds, using a Robinson annulation?

a.

Which of the following compounds will decarboxylate when heated?

a.

b.

Which of the following compounds will decarboxylate when heated?

What alkyl bromide(s) should be used in the malonic ester synthesis of each of the following carboxylic acids?

a. propanoic acid

b. 2-methylpropanoic acid

Explain why the following carboxylic acids cannot be prepared by a malonic ester synthesis:

c.

What alkyl bromide should be used in the acetoacetic ester synthesis of each of the following methyl ketones? a. 2-pentanone

What alkyl bromide should be used in the acetoacetic ester synthesis of each of the following methyl ketones? b. 2-octanone

What alkyl bromide should be used in the acetoacetic ester synthesis of each of the following methyl ketones? c. 4-phenyl-2-butanone

Design a synthesis for each of the following compounds using the given starting material:

b.

Design a synthesis for each of the following compounds using the given starting material:

d.

Draw a structure for each of the following:

a. ethyl acetoacetate

Draw a structure for each of the following:

b. a-methylmalonic acid

Draw a structure for each of the following:

c. a β-keto ester

Draw a structure for each of the following: d. the enol tautomer of cyclopentanone

Draw the products of the following reactions:

a. diethyl heptanedioate: (1) sodium ethoxide; (2) HCl

Draw the products of the following reactions: b. pentanoic acid + PBr₃ + Br₂, followed by hydrolysis

Draw the products of the following reactions:

c. acetone + LDA/THF: (1) slow addition of ethyl acetate; (2) HCl

Draw the products of the following reactions: e. diethyl malonate: (1) sodium ethoxide; (2) isobutyl bromide; (3) HCl, H₂O + heat