Hydroboration Reaction with BD3

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The discussion focuses on the hydroboration/oxidation reaction of 1-methylcyclopentene with deuterated borane, BD3. Participants explore whether the product would differ from that of a reaction using BH3, noting that deuterium (D) and hydroxyl (OH) would be added to the final product. The mechanism is emphasized as crucial for understanding the outcome, with a specific mention of producing 3,4-dideuterio-3-hexene. The conversation also touches on the method for carrying out the reaction, suggesting the use of D2 with a Lindlar catalyst for adding deuterium across the double bond. Overall, the thread provides insights into the expected products and reaction mechanisms involving deuterated reagents.
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Homework Statement


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

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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!
 
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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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