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1-Hexyne is treated with sodium hydride, followed by bromoethane. Lindlar hydrogenation of the resulting product affords what final product?Select answer from the options below(E)-2-octene(E)-3-octeneoctane(Z)-2-octene(Z)-3-octene

Question

1-Hexyne is treated with sodium hydride, followed by bromoethane. Lindlar hydrogenation of the resulting product affords what final product?Select answer from the options below(E)-2-octene(E)-3-octeneoctane(Z)-2-octene(Z)-3-octene

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Solution

Claro, aquí tienes la respuesta paso a paso:

  1. Tratamiento de 1-Hexino con hidruro de sodio:

    • El 1-Hexino (CH≡C-CH2-CH2-CH2-CH3) reacciona con el hidruro de sodio (NaH) para formar el anión acetiluro.
    • La reacción es: CH≡C-CH2-CH2-CH2-CH3 + NaH → CH≡C-CH2-CH2-CH2-CH3^- Na^+ + H2
  2. Adición de bromoetano:

    • El anión acetiluro reacciona con bromoetano (CH3-CH2-Br) en una reacción de sustitución nucleofílica.
    • La reacción es: CH≡C-CH2-CH2-CH2-CH3^- Na^+ + CH3-CH2-Br → CH≡C-CH2-CH2-CH2-CH2-CH3
  3. Hidrogenación con catalizador de Lindlar:

    • La hidrogenación parcial del alquino con el catalizador de Lindlar convierte el alquino en un alqueno con configuración cis (Z).
    • La reacción es: CH≡C-CH2-CH2-CH2-CH2-CH3 + H2 (con catalizador de Lindlar) → (Z)-3-octeno

Por lo tanto, el producto final es (Z)-3-octeno.

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