O-Chem Question

[iwork4911]

I was reviewing O-chem reactions and was looking over a chart that said a primary alkylhalide can't undergo an E2 reaction.

I can't seem to remember why that is. Anyone care to refresh my memory?

I was thinking that as long as there is a beta hydrogen to take it didn't much matter concerning E2.

thanks

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[baller99]

well i think its because the terminal alkene group would not be favored. but i was looking online and it says that it can sometimes occur with a bulky base.

http://members.aol.com/logan20/e2.html

might help you

 

[tco]

What chart was this? I can't think of any reason the reaction couldn't occur.

 

[HolyGrail]

It can undergo E2 only if you use potassium t-butoxide or anything really big. The problem is that the end product is not very stable, it doesn't have anywhere to distribute a charge, obviously this is not very desirable.

 

[lrkoehle]

I think it has to do with transition state stability. E2 on a primary alkyl halide is higher in energy and therefore less likely to occur in significan amounts.

use formaldehyde in a Wittig reaction to get a terminal alkene

 

[iwork4911]

The chart was given to my by my professor last year. I was just going through and reading up on reactions and I couldn't see why an E2 wouldn't work on a primary halide.

Anyway, makes sense now. Thanks for the replies, and may organic chem rot in the blasted acres of hades after the MCAT! hahahahahah