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When a THF Solution of Phenyl-2-Propanone and Bromobutane Is Treated

Question 36

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When a THF solution of phenyl-2-propanone and bromobutane is treated with 50% aqueous NaOH,poor yields of 3-phenyl-2-heptanone result.However,when a small amount of benzyltriethylammonium chloride is added to the reaction mixture,the yield of 3-phenyl-2-heptanone increases to 90%.Explain these results. When a THF solution of phenyl-2-propanone and bromobutane is treated with 50% aqueous NaOH,poor yields of 3-phenyl-2-heptanone result.However,when a small amount of benzyltriethylammonium chloride is added to the reaction mixture,the yield of 3-phenyl-2-heptanone increases to 90%.Explain these results.

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