Hydroboration Reaction with BD3

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SUMMARY

The hydroboration/oxidation reaction of 1-methylcyclopentene with deuterated Borane (BD3) results in the addition of a deuterium (D) atom and a hydroxyl (OH) group to the product. The mechanism involves the initial formation of a trialkylborane intermediate, followed by oxidation to yield the final alcohol. The discussion confirms that the product will be 3,4-dideuterio-3-hexene when using BD3, similar to the reaction with BH3, but with deuterium incorporated instead of hydrogen.

PREREQUISITES
  • Understanding of hydroboration/oxidation mechanisms
  • Familiarity with deuterated reagents, specifically BD3
  • Knowledge of alkene hydration techniques
  • Experience with Lindlar catalyst applications
NEXT STEPS
  • Research the detailed mechanism of hydroboration with BD3
  • Learn about the use of Lindlar catalyst in alkene hydrogenation
  • Explore the implications of using deuterated reagents in organic synthesis
  • Investigate the differences between reactions using BH3 and BD3
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Chemistry students, organic chemists, and researchers involved in synthetic organic chemistry or isotope labeling techniques.

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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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Write out the detailed mechanism and you will have your answer.
 
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!
 
Last edited:
What product would you get if you added H2 across the double bond? How about D2?
 
Ah, okay, I see your point now. I'd add D2 with the Lindlar catalyst instead. Thank you!
 

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