What is the expected product when 2-methylpropene undergoes hydroboration-oxidation?
Practice Questions
1 question
Q1
What is the expected product when 2-methylpropene undergoes hydroboration-oxidation?
2-methylpropan-1-ol
2-methylpropan-2-ol
2-methylpropanoic acid
2-methylpropene
Hydroboration-oxidation of 2-methylpropene leads to the formation of 2-methylpropan-1-ol due to anti-Markovnikov addition of water.
Questions & Step-by-step Solutions
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Q
Q: What is the expected product when 2-methylpropene undergoes hydroboration-oxidation?
Solution: Hydroboration-oxidation of 2-methylpropene leads to the formation of 2-methylpropan-1-ol due to anti-Markovnikov addition of water.
Steps: 7
Step 1: Understand that hydroboration-oxidation is a two-step reaction process.
Step 2: In the first step, hydroboration, borane (BH3) adds to the double bond of 2-methylpropene.
Step 3: The addition of borane occurs in a way that the boron atom attaches to the less substituted carbon of the double bond (anti-Markovnikov addition).
Step 4: This results in the formation of an organoborane intermediate.
Step 5: In the second step, oxidation, the organoborane is treated with hydrogen peroxide (H2O2) and a base (like NaOH).
Step 6: During oxidation, the boron atom is replaced by a hydroxyl group (OH), leading to the formation of an alcohol.
Step 7: The final product is 2-methylpropan-1-ol, which is the alcohol formed from the hydroboration-oxidation of 2-methylpropene.