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2. (a) In the molecule below, either halide can act as a leaving group. Please draw all elimination products which could reasonably form, and draw

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2. (a) In the molecule below, either halide can act as a leaving group. Please draw all elimination products which could reasonably form, and draw the arrow-pushing mechanism for the formation of any one of them. In your mechanism, draw the reactant in the conformation which actually undergoes the reaction. Also, for each product, indicate which reactant conformation accounts for its formation. (8 points) a Br HC-0 d CH HC-OH heat (b) Rank the products from major to minor. Explain your ranking as fully as possible. (4 points) (c) How would you expect the reaction to change if tert-butoxide (in BuOH solvent) were the base instead of methoxide? Would all the same products form, or would fewer, or more, or different products form? Would the ratio of products change (major/minor)? If so, how? Again, explain as fully as you can. (4 points) (d) Suppose a t-butyl group is added, as below (and base is back to methoxide). How would this change the outcome of the reaction (assume the t-butyl group is too large to occupy an axial position)? (3 points) C1 ...Br HC-0 "CH HC-OH heat

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