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Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: rhyang on June 26, 2009, 05:21:51 PM

Title: Alkene hydrogenation and ozonolysis question. Help please.
Post by: rhyang on June 26, 2009, 05:21:51 PM

Draw the structure of a hydrocarbon that absorbs two molar equivalents of H2 on catalytic hydrogenation and gives only butanedial on ozonolysis.

I'm totally confused on this one. I don't know where to start, because during ozonolysis don't you get two structures usually? Which separate from the double bond, then become carbonyls? I'm lost, help me please! And thank you!

Title: Re: Alkene hydrogenation and ozonolysis question. Help please.
Post by: rhyang on June 26, 2009, 05:38:46 PM

Actually I think I figured it out, but can anyone verify for me?

Is the answer a 1,3 cyclobutene? Something like that? This is what I put down so far,

Title: Re: Alkene hydrogenation and ozonolysis question. Help please.
Post by: 408 on June 26, 2009, 07:32:16 PM

no, that would form glyoxal.

Need a bigger ring, but you are on the right track with cyclics.

Title: Re: Alkene hydrogenation and ozonolysis question. Help please.
Post by: rhyang on June 26, 2009, 10:11:33 PM

Hm I'll need a bigger ring? And also, is it supposed to create 2 of those butanedials? So that would mean it should be a cyclooctene? Correct?

Title: Re: Alkene hydrogenation and ozonolysis question. Help please.
Post by: 408 on June 26, 2009, 10:25:48 PM

well cyclooctadiene yes, 1,5 to be precise.

Title: Re: Alkene hydrogenation and ozonolysis question. Help please.
Post by: rhyang on June 26, 2009, 10:28:53 PM

Ah. Thanks for the *delete me* Really appreciate it.