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
Solution
Claro, aquí tienes la respuesta paso a paso:
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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
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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
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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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