Chapter 23: Q46. (page 924)
Question: Synthesize each compound from diethyl malonate. You may use any other organic or inorganic reagents.
Short Answer
Answer
The starting materials needed to prepare each compound are shown below.
Chapter 23: Q46. (page 924)
Question: Synthesize each compound from diethyl malonate. You may use any other organic or inorganic reagents.
Answer
The starting materials needed to prepare each compound are shown below.
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Get started for freeQuestion: Treatment of ethyl acetoacetate with NaOEt (2 equiv) and BrCH2CH2Brforms compound X. This reaction is the first step in the synthesis of illudin-S, an antitumor substance isolated from thejack-oโ-lantern, a poisonous, saffron-colored mushroom. What is the structure of X?
Question: Treatment of ฮฑ, ฮฒ-unsaturated carbonyl compound X with base forms the diastereomer Y. Write a stepwise mechanism for this reaction. Explain why one stereogenic center changes configuration but the other does not.
Question: Both pentane-2,4-dione and ethyl acetoacetate have two carbonyl groups separated by a single carbon atom. Although an equilibrium mixture of pentane-2,4-dione tautomers contains 76% of the enol forms, an equilibrium mixture of ethyl acetoacetate tautomers contains only 8% of the enol forms. Suggest a reason for this difference.
Question: Draw the product formed when each starting material is treated with LDA in THF solution at โ780C.
Question: What alkyl halides are needed to prepare each ketone using the acetoacetic ester synthesis?
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