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An Alternate Synthesis of Oxiranes

An Alternate Synthesis of Oxiranes. An Alternate Synthesis of Oxiranes. What type of reaction does this look like? a. S N 1 b. S N 2 c. E1 d. E2 e. Addition. Reactivity of Oxiranes. If the ring is highly strained, does that make it more or less stable?

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An Alternate Synthesis of Oxiranes

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  1. An Alternate Synthesis of Oxiranes

  2. An Alternate Synthesis of Oxiranes What type of reaction does this look like? a. SN1 b. SN2 c. E1 d. E2 e. Addition

  3. Reactivity of Oxiranes • If the ring is highly strained, does that make it more or less stable? a. less b. more c. neither

  4. Reactivity of Oxiranes • Will it be more or less reactive? a. more b. less c. neither

  5. Base Catalyzed Ring Opening

  6. Base Catalyzed Ring Opening • Would RO- be a good leaving group? a. yes b. no

  7. Base Catalyzed Ring Opening • In order for the reaction to occur, it must be energetically favorable (exothermic, exergonic). What energetically favorable process occurs here? a. Relief of ring strain b. Formation of stabilized anion c. Breaking of C-O bond d. Loss of hydroxide anion

  8. Base Catalyzed Ring Opening • Since the reaction is reminiscent of an SN2 reaction, to which side will the hydroxide ion attach?     a. right C b. left C c. no preference

  9. Acid Catalyzed Ring Opening • Which resonance structure will be more important, A or B?

  10. Acid Catalyzed Ring Opening • Based on which resonance structure is more favorable, which product is more likely to form (a. top or b. bottom)?

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