[plexx92]

Im interested in the possible reactions necessary to change a secondary alcohol into an alkene chain. (R-OH ----> R-CH2CH=CH2) The correct isomer is important! The chain should make a zig zag formation, not a semi hexagon. I've looked through the reactions on this website:
http://www.cliffsnotes.com/study_guide/Reactions-of-Alcohols.topicArticleId-23297,articleId-23272.html
I can't figure it out. I know it's possible to do it in one step but easier to do it in two.
What I was wondering is if anyone could point me in the direction of some reactions that will help me achieve this?

[orgopete]

I don't see how you could perform that preparation in one step. It looks like a two step synthesis. This is my guess, you are studying organometallic reagents such as the Gilman reagent.

[mnakhla]

oxidizing the alcohol to the ketone then preforming an Horner-Wadsworth-Emmons reaction  could do this, though you were not specific on other functional groups that you may have around or what specifically you are trying to make?

[plexx92]

Since it's theoretical, assume that I have unlimited access to chemicals. I was just thinking about this.

[Doc Oc]

I think you can just do this with an acid catalyst.  If you can facilitate E2 elimination, you'll get the antiperiplanar geometry you're looking for.

[plexx92]

Im still working on this problem! It seems there are many different routes for alkene chains but I cant seem to get the 1-butene chain on there. The alkene bond needs to be on the far side, away from the R.

[billnotgatez]

if you get this to work, will it also work changing ethanol to ethene or maybe ethane at room temperature.

by the way ethene does not pass spell check

[plexx92]

I don't know, right now. I'm resorting to a alkyl halides and I'm not happy about it. The previous posts have pointed me in the right direction but so far I have not been able to find a way to changed [R-OH] to [R-CH2-CH=CH3] in a zig zag isomer

[plexx92]

Right now the only possibility I've come up with is converting to a ketone, using a wolff kishner reduction. Then making it into an alkene. And I'm not even sure that it will produce the right isomer!!!!

[discodermolide]

Right now the only possibility I've come up with is converting to a ketone, using a wolff kishner reduction. Then making it into an alkene. And I'm not even sure that it will produce the right isomer!!!!

Look at Doc Oc's post!