What is the expected product when 1-butyne undergoes hydroboration-oxidation?
Practice Questions
1 question
Q1
What is the expected product when 1-butyne undergoes hydroboration-oxidation?
1-butanol
2-butanol
butanal
butyric acid
Hydroboration-oxidation of 1-butyne leads to the formation of 2-butanol due to anti-Markovnikov addition.
Questions & Step-by-step Solutions
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Q
Q: What is the expected product when 1-butyne undergoes hydroboration-oxidation?
Solution: Hydroboration-oxidation of 1-butyne leads to the formation of 2-butanol due to anti-Markovnikov addition.
Steps: 6
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.