Following is the structure of miconazole, the active

Chapter 22, Problem 23.5

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Following is the structure of miconazole, the active antifungal agent in a number of over-the-counter preparations, including Monistat, which are used to treat vaginal yeast infections. One of the compounds needed for the synthesis of miconazole is the trichloro derivative of toluene shown on its right. 2,4-Dichloro-1- chloromethylbenzene Toluene N N O Cl Cl Cl Cl Cl Cl Cl CH3 (a) Show how this derivative can be synthesized from toluene. (b) How many stereoisomers are possible for miconazole?

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