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1,1-Dibromo-5,5-dimethylhexane is treated first with excess sodium amide and quenched with water. Catalytic hydrogenation with the Lindlar catalyst affords what final product? (Give the correct IUPAC name.)

Question

1,1-Dibromo-5,5-dimethylhexane is treated first with excess sodium amide and quenched with water. Catalytic hydrogenation with the Lindlar catalyst affords what final product? (Give the correct IUPAC name.)

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Solution

Sure, let's break down the reaction step by step:

  1. Starting Material: 1,1-Dibromo-5,5-dimethylhexane

  2. First Reaction: Treatment with Excess Sodium Amide (NaNH₂)

    • Sodium amide is a strong base and can induce elimination reactions.
    • In this case, it will likely cause a double elimination of the two bromine atoms, leading to the formation of a triple bond (alkyne) between the first and second carbon atoms.
    • The product after this step is 5,5-dimethyl-1-hexyne.

  3. Quenching with Water:

    • Quenching with water will neutralize any remaining sodium amide and stabilize the alkyne formed.
    • The product remains 5,5-dimethyl-1-hexyne.

  4. Catalytic Hydrogenation with Lindlar Catalyst:

    • The Lindlar catalyst is used for the partial hydrogenation of alkynes to cis-alkenes.
    • Therefore, 5,5-dimethyl-1-hexyne will be hydrogenated to 5,5-dimethyl-1-hexene, specifically the cis isomer.

Final Product: The final product is cis-5,5-dimethyl-1-hexene.

IUPAC Name: (Z)-5,5-Dimethyl-1-hexene

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