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1. Each of the following transformations can be carried out in no more than three steps. Fill in the reagents required for each step. If a step is not needed, please put an "X" through that step. 2. Provide the products from the following reactions. Be sure to indicate stereochemistry if it is relevant! If more than one product is possible, please provide only the single most likely product. 3. Reaction analysis: provide the requested information in each of the following chemical transformations. Show all products unless otherwise indicated, and if any reaction results in a stereoisomeric mixture, draw one and indicate "+ enantiomer," "+ diastereomer," or "+ more than one stereoisomer" in the box. (note: Pd/CaCO3, PbO is comparable to Lindlar’s catalyst; only 1 molar equivalent of H2 is consumed) 4. Design a synthesis of the following target molecules using the indicated starting materials including all necessary reaction conditions and any necessary reagents for each step. a) b) c) 5. Rank the following series of molecules based on reactivity in an E2 reaction (Na i-OPr/ i-PrOH). (1= fastest E2, 4= slowest E2) 6. For each reaction below, draw the chair conformation that would be required for an E2 reaction and draw the product(s) that would be formed from that conformation. If more than one product can be formed, draw each product. If no product can be formed, write “no reaction”. Which reaction above would be the fastest? Which would be the slowest? Briefly support your answer in each case.

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