Hydroboration Reaction with BD3

[student 1]

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?

 

[chemisttree]

Write out the detailed mechanism and you will have your answer.

 

[2Win]

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!

 

[chemisttree]

What product would you get if you added H₂ across the double bond? How about D₂?

 

[2Win]

Ah, okay, I see your point now. I'd add D2 with the Lindlar catalyst instead. Thank you!