ochem question **elimination rxn**

[ddsshin]

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I am not sure if this is an error in the DAT destroyer book, but I think I am right on this.I have destroyer April, 2008 edition and if you look at #81. I amnot sure about this elimination rxn.
I have 2-chlorobutane and which reacts wih bulky base. The product is 1-butene, not 2-butene. This means that the product does not follow Zaitsev rule. I thought the more substituted alkenes are more stable therefore will be the product.... very confused... any suggestion????

 

[y0ssarian]

Bulky bases grab the most accessible proton, and form the kinetic product, which is often (but not always!) the less stable product. 2-butene is the thermodynamic product (more stable), but requires pulling off protons that hard relatively harder to reach.

 

[SnowDog]

Bulky bases have a hard time getting to the H on the highly substituted C. Therefore it will be easier to react with less substituted one.