OChem Reactant/Production Concept Qs

[A6project]

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"2-bromobutane" is added with "(CH3)3 CO K / (CH3)3 COH" , and the product is "1-butene"

why is that instead of 2-butene?? My guess is that this rxn goes through E1 (not very good with E1,E2, SN1,SN2...) If so, could you explain a little bit? I think that since 2-butene is more stable, the rxn would go that way....

Plz help! thanks!!! 🙂

btw, its is from Destryoer Road Map5!

 

[herkulease]

my understanding is that because we are using a bulky base.

it results in a hoffman product(the least substituted). rather than one that follows zaitsev's rule of a more substituted product.

 

[UndergradGuy7]

What herkulease said is right. If you have a bulky base or a bulky leaving group you get the less substituted product. This is called Hoffman's rule.

 

[orgohacks]

"2-bromobutane" is added with "(CH3)3 CO K / (CH3)3 COH" , and the product is "1-butene"

why is that instead of 2-butene?? My guess is that this rxn goes through E1 (not very good with E1,E2, SN1,SN2...) If so, could you explain a little bit? I think that since 2-butene is more stable, the rxn would go that way....

Plz help! thanks!!! 🙂

btw, its is from Destryoer Road Map5!

The only time you should really be thinking about E1 is with a tertiary carbon, and even then, usually when acid is involved.

When you see (CH3)3COK (or related bulky bases) you should have a Pavlovian response for E2.