# Solve BH3*THF vs. HBr/ROOR Transformation

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.

## 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.

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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