Destroyer #71 ochem

[polarmolar]

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Two things:

In the first step wouldn't the carbocation shift to create C-C=C-C instead of C-C-C=C?

Also, why does Br2/CCl4 add syn?

 

[PooyaH]

There are only 3 carbon atoms though! Actually I put up a thread about Br2/CCl4 being trans and not syn, I think it's just a small mistake...it should be trans!

 

[ongmeister]

There are only 3 carbon atoms though! Actually I put up a thread about Br2/CCl4 being trans and not syn, I think it's just a small mistake...it should be trans!

There are 4 carbons in my destroyer, did u count them right? or is my destroyer the outdated 2007 version? 🙁

And the Br/CCl4 should be in trans like PooyaH said.

 

[PooyaH]

There are 4 carbons in my destroyer, did u count them right? or is my destroyer the outdated 2007 version? 🙁

And the Br/CCl4 should be in trans like PooyaH said.

Mine's 2008 version and what I have here is CH3CH2CH2OH (propanol)

 

[ongmeister]

Mine's 2008 version and what I have here is CH3CH2CH2OH (propanol)

Problem solved, hehe, the 2007 version it is ch3ch2ch2ch3OH. 😀

 

[polarmolar]

In the 2007 one it has 4 carbons so yea, what do you think ongmeister?

 

[PooyaH]

In the 2007 one it has 4 carbons so yea, what do you think ongmeister?

What is the first reagent?

 

[ongmeister]

In the 2007 one it has 4 carbons so yea, what do you think ongmeister?

It should be what you put in the above, your right. I think Orgo man revised it because it was wrong in the edition that we have. It should still form A though, if u work it out.

It should be CH3CH=CHCH3 then u add the Br in trans, then when u add in the NANH3 and H20, it gives u a triple bond, after that the HgSO4 solution adds to the either side of the double bond, and it tautomerizes and you should get A. That's how I did it. Did u do the same?