Chapter 17: Q38P (page 833)
Which of the following compounds will decarboxylate when heated?

Short Answer
Compound showing decarboxylation is compound A and D, and E.
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Chapter 17: Q38P (page 833)
Which of the following compounds will decarboxylate when heated?

Compound showing decarboxylation is compound A and D, and E.
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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
c. 3-phenylpropanoic acid
d. 4-methylpentanoic acid
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.
b. Draw the mechanism for the conversion of A to C.
A compound known as Hagemann’s estercan be prepared by treating a mixture of formaldehyde and ethyl acetoacetate first with base and then with acid
and heat. Write the structure for the product of each of the steps.
a. The first step is an aldol-like condensation.
b. The second step is a Michael addition.
c. The third step is an intramolecular aldol addition.
d. The final transformation includes a dehydration and a hydrolysis followed by a decarboxylation.

Explain why the following bromoketone forms different bicyclic compounds under different reaction conditions:

Draw the products of the following reactions:
a. 1,3-cyclohexanedione + LDA/THF, followed by allyl bromide
b. g-butyrolactone + LDA/THF, followed by methyl iodide
c. 2,7-octanedione + sodium hydroxide
d. diethyl 1,2-benzenedicarboxylate + sodium ethoxide: (1) slow addition of ethyl acetate; (2) HCl
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