Question

4. You are the chief organic chemist at Bugs and Slugs, Inc., a company that specializes in environmentally friendly pest control. a) You have been asked to design a synthesis

of 4-methyl-3-heptanol, the aggregation pheromone of the European elm beetle (the carrier of Dutch elm disease). Propose DOa synthesis of this compound from starting materials that contain five carbon atoms or less. b) After successfully completing the synthesis in (a) and delivering your compound, you are advised that it appears to be a mixture of isomers. Assuming that you have synthesized the correct compound, provide an explanation.

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