[gregpawin]

Hi guys, I rarely ask too many questions myself but I've been boning up on my organic and had a question that always bothered me.  Perhaps my book isn't too specific, (McMurry for those who ask, which I'm not sure is high or low on the legitimate organic chemist's bookshelf), but they cite a reaction to turn alcohols into an alkene with a strong acid and heat (specifically sulfuric in THF at 50 C), but only say a strong acid suffices.

However, in just a few chapters they cite the creation of alkyl halides by HX where X is Cl, Br, or I, in ether.

Question: Since HX is also a strong acid, why doesn't this reaction instead produce alkenes?

[Mitch]

You need a non-nucleophilic strong acid.

I still know my stuff.

[gregpawin]

So the acid used to make alkenes has to be non-nucleophilic...

[Mitch]

yes

[gregpawin]

Is there a touch of insecurity I hear?  Poor be the organic chemist for they worship their abilities like giant phallic idols and suffer accordingly if it is torn down.

jk... your organic skills are still there mitch