[rengb6]

Hello! Ok I have a quick question. What alkyne that does not contain O is best used to make the compound shown? The product is : H3C-CH2-CH2-CH2-CH2-CH3 with a double bonded O on the second to last Carbon (the last CH2). So my attempt at a solution was to do hydroboration-oxidation of the alkyne and while that does produce this product it also produces another product. Can any one help me think of another reaction that might work? I have tried adding big groups like Br on one side of the alkene so that maybe it would favor a specific carbon but that didnt work. I must also keep that tripple bond between carbons 3 and 4. Also, I tried Hydration and it didn't work either. Thanks!

[discodermolide]

Hello! Ok I have a quick question. What alkyne that does not contain O is best used to make the compound shown? The product is : H3C-CH2-CH2-CH2-CH2-CH3 with a double bonded O on the second to last Carbon (the last CH2). So my attempt at a solution was to do hydroboration-oxidation of the alkyne and while that does produce this product it also produces another product. Can any one help me think of another reaction that might work? I have tried adding big groups like Br on one side of the alkene so that maybe it would favor a specific carbon but that didnt work. I must also keep that tripple bond between carbons 3 and 4. Also, I tried Hydration and it didn't work either. Thanks!

Perhaps you could draw out your reaction, it will make your question clearer to follow.

[Babcock_Hall]

I agree with discodermolide.  Your title suggests that you want to make an aldehyde, but your text suggests you want to make a ketone.