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Solved: Starting with acetylene as your only source of
Chapter 12, Problem 12.31(choose chapter or problem)
Starting with acetylene as your only source of carbon atoms, propose a plausible synthesis for 1,4- dioxane: O O 1,4-Dioxane
Questions & Answers
QUESTION:
Starting with acetylene as your only source of carbon atoms, propose a plausible synthesis for 1,4- dioxane: O O 1,4-Dioxane
ANSWER:Step 1 of 5
The final question in this chapter asks us to prepare 1,4-dioxane using acetylene as the only source of carbon atoms. The Williamson ether synthesis is one of the most powerful methods of preparing ethers, and the target compound has two ethers present. If you examine the structure of 1,4-dioxane, you see that both the left and right hand sides of the molecule contain a two-carbon molecular fragment. Since acetylene contains two carbons, it’s a good bet that we're going to need to use acetylene to prepare those sections.
The Williamson ether synthesis requires a good nucleophile and a good electrophile, so that the SN2 reaction can proceed. In this case (because we're actually forming two ethers) we need one intermediary to have two nucleophilic atoms, and the other to have two electrophilic atoms. Even when restricted to just acetylene as the source of carbon atoms, this task is easily completed by accessing the chemistry of alkenes.