Question
Download Solution PDFReaction of alkyne with a solution of an alkali metal in liquid ammonia gives:
Answer (Detailed Solution Below)
Detailed Solution
Download Solution PDFCONCEPT:
Reaction of alkyne with alkali metal in liquid ammonia
- The reaction of an alkyne with an alkali metal in liquid ammonia leads to the reduction of the alkyne.
- This reduction specifically results in the formation of a trans alkene.
- The reaction is known as the Birch reduction.
- In this reaction:
- Liquid ammonia acts as the solvent and provides protons.
- Alkali metal (e.g., sodium or lithium) provides electrons, which reduce the alkyne.
EXPLANATION:
- When an alkyne reacts with an alkali metal in liquid ammonia:
- The alkali metal donates electrons to the triple bond of the alkyne, breaking it into a double bond.
- Subsequent protonation (addition of protons from ammonia) leads to the formation of a trans alkene.
- The reaction proceeds in a stereoselective manner, favoring the trans configuration over the cis configuration.
- This is because the trans alkene is more stable due to minimized steric hindrance between the substituents.
Therefore, the correct answer is Trans alkene.
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