HardChemistryHigh School (11–12)Organic Compounds with Functional Groups › Alcohols, Phenols and EthersNumerical
A chemist makes butan-1-ol from but-1-ene by hydroboration followed by oxidation…
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A chemist makes butan-1-ol from but-1-ene by hydroboration followed by oxidation. She uses of but-1-ene. Use for but-1-ene and for diborane, . Each BH unit reacts with three alkene molecules. Find the amount of but-1-ene, the amount of BH needed and the mass of diborane that supplies it.
Need a reminder? The key ideaShow
Acid hydration puts OH on the more substituted carbon. Hydroboration then oxidation puts it on the less substituted carbon, and one BH takes three alkene molecules. NaBH reduces four C=O groups for each formula unit. A Grignard reagent adds its R group to the carbonyl carbon. Yield .
The worked solution
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Work it out on paper first. It is fine to get stuck or make a mistake: that is how we learn. When you are ready, go through the solution one step at a time, and check each step against your own.
Given. of but-1-ene.
Step 1. Alkene. .
Step 2. Borane. . One BH to three alkene molecules: .
Step 3. Diborane. One gives two BH, so of diborane. Mass: .
Check. Diborane is a toxic gas that catches fire in air. In the laboratory it is used as a solution of borane in tetrahydrofuran.
Answer: , and .
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