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Solved: Using any compounds that contain two carbon atoms
Chapter 12, Problem 12.25(choose chapter or problem)
Using any compounds that contain two carbon atoms or fewer, show a way to prepare a racemic mixture of (2R,3S)- and (2S,3R)-2,3- dihydroxypentane.
Questions & Answers
QUESTION:
Using any compounds that contain two carbon atoms or fewer, show a way to prepare a racemic mixture of (2R,3S)- and (2S,3R)-2,3- dihydroxypentane.
ANSWER:Step 1 of 3
The necessary alkyne (and subsequent alkenes) needs a methyl group on one side and an ethyl group on the other side. Because acetylides are very good nucleophiles, the easiest way to build up the needed skeleton is to use a sequence of reactions. Treatment of acetylene with sodium amide followed by methyl iodide gives propyne; additional treatment with sodium amide followed by ethyl iodide gives the necessary alkyne intermediate.
