Solve BH3*THF vs. HBr/ROOR Transformation

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In summary, the most efficient method to carry out the transformation from but-1-ene to butyl cyanide is by using HBr and peroxide followed by NaCN.
  • #1
Adsit_Deus
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Homework Statement



What series of steps could be used to carry out the transformation shown below

Homework Equations



but-1-ene → Butyl cyanide

The Attempt at a Solution



This is a practice problem, so I already know that the answer is 1) HBr + Peroxide, 2) NaCN, but could it not also be BH3*THF and NaCN? My guess as to why that might not work is because Br is a much better leaving group than the boron group, but I just wanted to be sure.
 
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  • #2


Yes, your reasoning is correct. While both methods can be used to carry out the transformation, the first method using HBr and peroxide is more efficient because the bromine atom is a better leaving group compared to the boron group. In addition, the use of peroxide helps to generate a radical intermediate which can then react with NaCN to form the desired product. Using BH3*THF and NaCN may also result in side reactions and lower yields.
 

1. What is the purpose of the BH3*THF vs. HBr/ROOR transformation?

The BH3*THF vs. HBr/ROOR transformation is a chemical reaction used to convert alkenes into alcohols. The purpose of this transformation is to add a hydroxyl group (OH) to the carbon-carbon double bond of an alkene, resulting in the formation of an alcohol.

2. How does BH3*THF differ from HBr/ROOR in this transformation?

BH3*THF (borane-tetrahydrofuran) and HBr/ROOR (hydrobromic acid with an organic peroxide) are two different reagents used in this transformation. BH3*THF is a Lewis acid, meaning it accepts an electron pair from another molecule, while HBr/ROOR is a Brønsted acid, meaning it donates a proton to another molecule. These two reagents have different mechanisms for the addition of a hydroxyl group to an alkene, resulting in different products.

3. What are the benefits of using BH3*THF vs. HBr/ROOR in this transformation?

One benefit of using BH3*THF over HBr/ROOR is that it is more selective and produces a single alcohol product. HBr/ROOR, on the other hand, can produce multiple alcohol products due to its radical mechanism. Additionally, BH3*THF is a milder reagent, making it more suitable for sensitive or complex molecules.

4. What factors should be considered when choosing between BH3*THF vs. HBr/ROOR?

The choice between BH3*THF and HBr/ROOR depends on the specific reaction conditions and the desired product. BH3*THF is more suitable for reactions with electron-rich alkenes, while HBr/ROOR is better for electron-deficient alkenes. The presence of other functional groups or the need for selectivity may also influence the choice of reagent.

5. Are there any safety concerns when working with BH3*THF or HBr/ROOR?

Both BH3*THF and HBr/ROOR can be hazardous chemicals and should be handled with caution. BH3*THF is flammable and toxic, and it should be handled in a well-ventilated area. HBr/ROOR can also be flammable and may release toxic gases when mixed with other chemicals. Proper protective equipment and safety procedures should be followed when working with either reagent.

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