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1-Hexyne is treated with sodium hydride, followed by bromoethane. Lindlar hydrogenation of the resulting product affords what final product?

Question

1-Hexyne is treated with sodium hydride, followed by bromoethane. Lindlar hydrogenation of the resulting product affords what final product?

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Solution

  1. Deprotonation of 1-Hexyne:

    • 1-Hexyne (CH≡C-CH₂-CH₂-CH₂-CH₃) is treated with sodium hydride (NaH).
    • Sodium hydride acts as a strong base and deprotonates the terminal alkyne, forming the acetylide anion (CH≡C⁻-CH₂-CH₂-CH₂-CH₃).

  2. Alkylation with Bromoethane:

    • The acetylide anion (CH≡C⁻-CH₂-CH₂-CH₂-CH₃) reacts with bromoethane (CH₃-CH₂-Br).
    • This results in an SN2 reaction where the acetylide anion attacks the carbon bonded to the bromine, displacing the bromide ion.
    • The product of this reaction is 1-octyne (CH≡C-CH₂-CH₂-CH₂-CH₂-CH₃).

  3. Lindlar Hydrogenation:

    • 1-Octyne (CH≡C-CH₂-CH₂-CH₂-CH₂-CH₃) is subjected to Lindlar hydrogenation.
    • Lindlar's catalyst selectively hydrogenates alkynes to cis-alkenes.
    • The final product is cis-1-octene (CH₂=CH-CH₂-CH₂-CH₂-CH₂-CH₃).

Therefore, the final product is cis-1-octene.

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