[ksuwildcat]

Is there a way to start with 4-nonyne and make 1-bromobutane?  What reactants would be used.  Don't need actual lab techniques just a general scheme.  Thanks

[movies]

Yeah, I think it would be possible, but probably difficult to carry out in the lab.

So what are the key things that need to be done to achieve the transformation?

[ksuwildcat]

cleavage of the double bond after a P2 catalyst.  then adding a bromine.  The tough part is cleaving the bond without it oxidating to a ketone or aldehyde (i could be wrong.)  A theoretical scheme would do.  Thanks

[movies]

Okay, I think you have the same idea that I did.

How would you propose to cleave the double bond?

What ways do you know to introduce a bromine?  What functional groups can you convert to Br?

[ksuwildcat]

well i don't know how to change an aldehyde or ketone to a straight chain alkane.  If this was accomplished then reacting it with HBr would suffice.  O3 or Potassium Permanganate would cleave as well, but to the aldehyde and ketone
Any ideas?

[movies]

Are you familiar with the reagent PBr₃?

[AWK]

4-nonyne

contains a triple bond which can be easily broken by ozone. The resulting butanal (and pentanal) can be reduced to butyl and pentyl alcohols. After separation, the butyl alcohol can be converted to bromide by PBr3 or by warming with concentrated HBr.

[dexangeles]

contains a triple bond which can be easily broken by ozone. The resulting butanal (and pentanal) can be reduced to butyl and pentyl alcohols. After separation, the butyl alcohol can be converted to bromide by PBr3 or by warming with concentrated HBr.

I was thinking the same reaction, might as well just cleave it all the way then reduce to an alcohol, but....I believe Ozonolysis will cleave a triple bond to form a carboxylic acid instead (which can still be reduced), and it cleaves a double bond into an aldehyde or ketone.

Just making sure he uses the correct reducing agent

[AWK]

I was thinking the same reaction, might as well just cleave it all the way then reduce to an alcohol, but....I believe Ozonolysis will cleave a triple bond to form a carboxylic acid instead (which can still be reduced), and it cleaves a double bond into an aldehyde or ketone.

Just making sure he uses the correct reducing agent

Right, I lost reduction with Lindlar catalyst before ozonolysis