Anti-coplanar H in E2 reactions

This forum made possible through the generous support of SDN members, donors, and sponsors. Thank you.

Toadesque

Full Member
15+ Year Member
Joined
Jul 12, 2007
Messages
423
Reaction score
58
Confused about this

Here's a reaction from Chad's quizzes

LrmonHM.png


Here's the answer:

bMhcuMB.png


So here you have a strong Nuc and a strong base and a tertiary halide. This tells you it's an E2 reaction and not Sn2, I get that.

I don't really understand the concept of the whole co-planar hydrogen thing though and why the more substituted alkene (Zaitsev's) doesn't form instead, i.e this one

j5sa2WG.png


Should I just assume that a tertiary halide along with a strong base is going to be Anti-Zaitsev?

Members don't see this ad.
 
just draw all the Alpha hydrogens, you'll see that all of them go backward out of the plane of the page except the one on CH3 group directly attached to Br. Basically, there's no hydrogen on the dash position for the base to pull from on both adjacent positions.

"Should I just assume that a tertiary halide along with a strong base is going to be Anti-Zaitsev?"
If you eliminate the CH3 group on the top, you're gonna have both hydrogens that are on wedge/dash position, so you can get a more substituted product (compared to the one in this example)
 
Top