Week_3.2_PurpleBook_Answers

Week_3.2_PurpleBook_Answers - 66 An Introduction to SN2,...

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Br OH Br Br OH OH An Introduction to S N 2, E2, S N 1, and E1 Mechanisms H 1. Provide complete curved-arrow mechanisms for the following transformations. conc. H 2 SO 4 O H H +B r tBuO: +B r +tBuOH + O H H + :Solvent + H + :Solvent OH KO t Bu H 2 O HO: :OH 2 H +
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CH 3 H Br O O SH HO O S Br Br OH HO Mechanisms and Stereochemistry SCH 3 CH 3 H H 1. Predict the product. 3. Explain the difference in reactivity. Br :O O SH 2. Provide a curved-arrow mechanism, and explain the observed stereochemistry. no reaction! SH O O but S: O O conc. 4. Explain the difference in reactivity. conc. no reaction! :O O S but Br H HO—H axial Br perfect for antiperiplanar E2 elimination With S N 2, "retention" is ALWAYS "double inversion" Br equatorial Br can't get antiperiplanar with any H, so can't do E2 elimination. E1 elim. OK, with secondary carbocation which can be planar (as required) + This tertiary carbocation cannot be planar, and the product violates Bredt's Rule
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Week_3.2_PurpleBook_Answers - 66 An Introduction to SN2,...

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