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Question 20.38: Fatty acids from natural sources are long-chain unbranched c......

Fatty acids from natural sources are long-chain unbranched carboxylic acids that contain an even number of carbon atoms. Outline steps to convert the readily available dodecanoic acid (lauric acid) into the rare tridecanoic acid.

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First, reduce the carboxylic acid to dodecanol. Second, use PBr₃ to give 1-bromododecane. Third, prepare the Grignard reagent using magnesium and ether. Fourth, add the Grignard reagent to carbon dioxide, followed by acidification in workup.

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