Problem: Provide an efficient multistep synthesis for each of the following conversions of the given starting material into product. For each multistep synthesis, you must use the given starting organic compound, and you may use any organic compound with fewer than 4 carbons to provide carbon atoms that end up in the final product. For each functional group transformation, give all necessary reagents, solvents, and catalysts; give a structural formula of the organic reactant and the major organic product(s). Show stereochemistry appropriately when necessary. If a mixture of products (for example an ortho-para mixture or a mixture of diastereomers) must be present after a step, assume that you can separate the mixture and take the one needed product forward through the next step. Remember that you cannot use ClCO2H or HCOCl in a Friedel- Crafts acylation reaction. Also remember that you cannot make a Grignard reagent or an organolithium compound from an acyl halide.

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Problem Details

Provide an efficient multistep synthesis for each of the following conversions of the given starting material into product. For each multistep synthesis, you must use the given starting organic compound, and you may use any organic compound with fewer than 4 carbons to provide carbon atoms that end up in the final product. For each functional group transformation, give all necessary reagents, solvents, and catalysts; give a structural formula of the organic reactant and the major organic product(s). Show stereochemistry appropriately when necessary. If a mixture of products (for example an ortho-para mixture or a mixture of diastereomers) must be present after a step, assume that you can separate the mixture and take the one needed product forward through the next step. Remember that you cannot use ClCO2H or HCOCl in a Friedel- Crafts acylation reaction. Also remember that you cannot make a Grignard reagent or an organolithium compound from an acyl halide.

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