Chapter 17: Q42P (page 835)
Starting with methyl propanoate, how could you prepare 4-methyl-3-heptanone?

Short Answer

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Chapter 17: Q42P (page 835)
Starting with methyl propanoate, how could you prepare 4-methyl-3-heptanone?


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Describe how the following compounds could be prepared from cyclohexanone using an enamine intermediate:
a.

b.

Explain why 92% of 2,4-pentanedione exists as the enol tautomer in hexane but only 15% of this compound exists as the enol tautomer in water.
Draw the product obtained by heating each pair of ketones in a basic solution.


A student tried to prepare the following compounds using aldol condensations. Which of these compounds was she successful in synthesizing? Explain why the other syntheses were not successful.

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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