Problem: The Wittig reaction can be used to prepare carbon-carbon double bond containing compounds from an alkyl halide and a carbonyl compound. Which of the following combinations would not yield compound 1? (Note: all except one will work, which one?)

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The Wittig reaction can be used to prepare carbon-carbon double bond containing compounds from an alkyl halide and a carbonyl compound. Which of the following combinations would not yield compound 1? (Note: all except one will work, which one?)

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Based on our data, we think this problem is relevant for Professor Baldwin's class at OSU.