Why doesn't this elimination reaction follow Zaitsev's Rule?

[BMEEngineer]

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[IsaacYankem]

The reagent NaO(CH3)3 is bulky and will form the less substituted process via E2 mechanism.

That's the most common base they'll use and expect you to know it forms the anti-Zaitsev, Hofman product.

 

[KyoPhan]

This is a Bulky base! It produces the least substituted alkene.

Edit: LDA(bulky base) and hoffman elim will also give you the last substituted.

 

[BMEEngineer]

Thanks to you both! I hadn't actually seen the tert-butoxide in chemical form, so now I know to recognize it both ways!

 

[KyoPhan]

LDA is also a bulky base, so keep an eye out for that as well.

 

[KyoPhan]

Also, hoffman elimination (with amines) gives similar product.