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1. Complete the following reactions by giving the structures of the missing reactant, necessary reagents or major organic product where there is a question mark.

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1. Complete the following reactions by giving the structures of the missing reactant, necessary reagents or major organic product where there is a question mark. Note: some transformations may require more than one step and these steps must be indicated clearly. Indicate stereochemistry where appropriate. ? Br Br i) 1) KOH, alcohol, heat OH ? 'OH 2) meta-chloroperbenzoic acid (MCPBA) 3) H20, H+ ii) H BI CH3 KOH, EVOH/heat ? (E-2 elimination) iii) H 2. Show how to carry out the following transformations. For each step in your synthesis, clearly show all reagents and reaction conditions (hint: consider using the following reaction types in your syntheses: elimination, addition and oxidation reactions). Br H So Br Br OH Br CH3 " OH OH H CH3 1. Complete the following reactions by giving the structures of the missing reactant, necessary reagents or major organic product where there is a question mark. Note: some transformations may require more than one step and these steps must be indicated clearly. Indicate stereochemistry where appropriate. ? Br Br i) 1) KOH, alcohol, heat OH ? 'OH 2) meta-chloroperbenzoic acid (MCPBA) 3) H20, H+ ii) H BI CH3 KOH, EVOH/heat ? (E-2 elimination) iii) H 2. Show how to carry out the following transformations. For each step in your synthesis, clearly show all reagents and reaction conditions (hint: consider using the following reaction types in your syntheses: elimination, addition and oxidation reactions). Br H So Br Br OH Br CH3 " OH OH H CH3

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