Hydroboration Reaction with BD3

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In summary, the product of a Hydroboration/oxidation reaction of 1-methylcyclopentene with deuterated Borane, BD3 would result in the addition of a D and an OH group. The reaction can be carried out by hydrating with H2 and a Lindlar catalyst, followed by the addition of D2 with the same catalyst.
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Homework Statement


What would be the product of a Hyrdroboration/ oxidation reaction of 1-methylcyclopentene with deuterated Borane, BD3?

Homework Equations





The Attempt at a Solution

I know the solution for a reaction with BH3. However, would this give you the same answer or a totally different one?
 
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  • #2
Write out the detailed mechanism and you will have your answer.
 
  • #3
Ummm, so does that mean that a D and an OH will be added? Because that's what I get when I write it out, and I'm not sure if that's right...

Also, how would one carry out this reaction?

3-hexyne ----------------> 3,4-dideuterio-3-hexene

I know the first step would be to hydrate with H2 and Lindlar catalyst, but how would you go about adding the two D's?

-Thanks!
 
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  • #4
What product would you get if you added H2 across the double bond? How about D2?
 
  • #5
Ah, okay, I see your point now. I'd add D2 with the Lindlar catalyst instead. Thank you!
 

1. What is the purpose of a Hydroboration Reaction with BD3?

The purpose of a Hydroboration Reaction with BD3 is to add a hydroxyl group (-OH) to an alkene or alkyne molecule. This process is known as hydroboration and it is often used in organic synthesis to create various alcohols.

2. How does the Hydroboration Reaction with BD3 work?

The Hydroboration Reaction with BD3 involves the addition of a boron atom from BD3 to the alkene or alkyne double or triple bond. This is followed by the addition of a hydroxyl group (-OH) to the boron atom, resulting in the formation of an alcohol.

3. What are the benefits of using BD3 in a Hydroboration Reaction?

BD3 is a highly reactive and selective reagent, meaning it can specifically target and add a hydroxyl group to an alkene or alkyne without affecting other functional groups in the molecule. This makes it a valuable tool in organic synthesis for creating specific alcohols.

4. What are the limitations of using BD3 in a Hydroboration Reaction?

One limitation of using BD3 in a Hydroboration Reaction is that it requires careful handling as it is a highly toxic and flammable gas. Additionally, BD3 is moisture sensitive, so precautions must be taken to ensure it is properly handled and stored to avoid any unwanted side reactions.

5. What are some practical applications of the Hydroboration Reaction with BD3?

The Hydroboration Reaction with BD3 has a wide range of practical applications in organic synthesis. It is commonly used in the production of pharmaceuticals, agrochemicals, and other fine chemicals. It can also be used in the synthesis of polymers and for functionalizing surfaces in material science.

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