Destroyer Ochem #80

[jjkim1232]

---

Members do not see this ad.

When a bulky base is added to 2-chlorobutane in an E2, wouldn't the more substituted (more stable) alkene form instead of the terminal alkene?

So 2-chlorobutane --Bulky base--> 2-butene

NOT 2-chlorobutane --Bulky base--> 1-butene


???????

 

[D.D.S.]

The bulky base, the name says it... its bulky.. so it rather rip off a hydrogen thats easier to reach. In this case, the terminal hygrogens on Carbon 1 (primary), are much easier to rip, than the hydrogen from Carbon 3 (secondary).

 

[jjkim1232]

double post

 

[jjkim1232]

Kaplan blue book page 363 (towards the bottom) says:

"Often there are two possible products. In such a case, the more substituted double bond is formed preferentially."

So I am assuming the above statement does not apply when dealing with a bulky base in which case the less substituted product ALWAYS results??

 

[D.D.S.]

Yes sir. The bulky base produces the least substituted product, where as a smaller, less bulky base produces the most substituted product.

I believe if you continue doing destroyer, you will get a hang of it because there are more problems involving this.

Good luck.

 

[jjkim1232]

It sure has....Thanks!