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Organic Chemistry 2 Midterm - Part 3 of 4
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21. Aldehydes and Ketones: Nucleophilic Addition / Wittig Reaction / Problem 15

Triphenylphosphine can be used to open epoxides via nucleophilic substitution. The initial substitution product (a betaine) quickly cyclizes to a 4-membered ring (oxaphosphetane) that collapses to triphenylphosphine oxide and an alkene. Draw the arrow-pushing mechanism for the reaction of trans-3,4-epoxyhexane and triphenylphosphine to produce hex-3-ene. Identify the specific stereoisomer of the product.

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