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Summary & Applications (Synthesis) S N 1 / E1 vs. S N 2 / E2

Summary & Applications (Synthesis) S N 1 / E1 vs. S N 2 / E2. E2 and E1 Reactions. Substitution vs. Elimination. Alkyl halides can undergo S N 2, S N 1, E2 and E1 Reactions. 1) Which reaction conditions favor S N 2/E2 or S N 1/E1? S N 2/E2 reactions are favored by a high

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Summary & Applications (Synthesis) S N 1 / E1 vs. S N 2 / E2

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  1. Summary & Applications (Synthesis) SN1 / E1 vs. SN2 / E2

  2. E2 and E1 Reactions

  3. Substitution vs. Elimination Alkyl halides can undergo SN2, SN1, E2 and E1 Reactions • 1) Which reaction conditions favor SN2/E2 or SN1/E1? • SN2/E2 reactions are favored by a high • concentration of nucleophile/strong base • SN1/E1 reactions are favored by a poor • nucleophile/weak base 2) What will be the relative distribution of substitution product vs. elimination product?

  4. Consider SN1/E1 vs. SN2/E2 Consider the Substrate

  5. NOTE: a bulky base encourages elimination over substitution

  6. Returning to Sn2 and E2:Considering the differences Can you predict the products? Can you explain the products?

  7. Substitution and Elimination Reactions in Synthesis

  8. A hindered alkyl halide should be used if you want to synthesize an alkene

  9. Which reaction produces an ether?

  10. Consecutive E2 Elimination Reactions: Alkynes

  11. Intermolecular vs. Intramolecular Reactions • A low concentration of reactant favors an intramolecular • reaction • The intramolecular reaction is also favored when a five- • or six-membered ring is formed

  12. Three- and four-membered rings are less easily formed Three-membered ring compounds are formed more easily than four-membered ring compounds The likelihood of the reacting groups finding each other decreases sharply when the groups are in compounds that would form seven-membered and larger rings.

  13. Designing a synthesis …

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