Chapter 23: Q31. (page 924)
Question: Draw enol tautomer(s) for each compound.



Short Answer
Answer
The enol tautomer(s) for each compound is shown below:
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Chapter 23: Q31. (page 924)
Question: Draw enol tautomer(s) for each compound.



Answer
The enol tautomer(s) for each compound is shown below:
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Question: Synthesize each compound from diethyl malonate. You may use any other organic or inorganic reagents.


Question: Draw the products obtained (including stereochemistry) when each compound is treated with LDA, followed by CH3l.



Question: Nabumetone is a pain reliever and anti-inflammatory agent sold under the brand name of Relafen.

a. Write out a synthesis of nabumetone from ethyl acetoacetate.
b. What ketone and alkyl halide are needed to synthesize nabumetone by direct enolate alkylation?
Question: The analgesic naproxen can be prepared by a stepwise reaction sequence from ester A. Using enolate alkylation in one step, what reagents are needed to convert A to naproxen? Write the structure of each intermediate. Explain why a racemic product is formed.

Question: Draw the product formed when each starting material is treated with LDA in THF solution at –780C.




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