What is the expected product when 1-butyne undergoes hydroboration-oxidation?

Practice Questions

Q1
What is the expected product when 1-butyne undergoes hydroboration-oxidation?
  1. 1-butanol
  2. 2-butanol
  3. butanal
  4. butyric acid

Questions & Step-by-Step Solutions

What is the expected product when 1-butyne undergoes hydroboration-oxidation?
  • Step 1: Understand that 1-butyne is an alkyne with the formula C4H6, specifically with a triple bond between the first and second carbon atoms.
  • Step 2: Know that hydroboration-oxidation is a two-step reaction process used to convert alkynes into alcohols.
  • Step 3: In the first step (hydroboration), a boron atom adds to the less substituted carbon of the alkyne (the first carbon in 1-butyne) due to anti-Markovnikov addition.
  • Step 4: This results in the formation of a trialkyl borane intermediate.
  • Step 5: In the second step (oxidation), the trialkyl borane is treated with hydrogen peroxide (H2O2) and a base, which replaces the boron with a hydroxyl group (OH).
  • Step 6: The final product is 2-butanol, which has the hydroxyl group on the second carbon, making it a secondary alcohol.
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