Elmination into two products

[Contach]

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Hi, So apparently Kaplan says this is wrong. It says the bottom product will actually be the major, and the one on top will actually be the minor. Can som1 explain to me how the products are different? On either side of the double bond both products are di- and mono-substituted.. To me these seem equally stable...

 

[soopasteve]

well what you need to remember is the number of viscinal hydrogens available to be eliminated. while there is only two types (both are on equally substituted carbons) one of them has two carbons and the other has one. if that is 3-ethylhexan-3-ol then if you look closely youll see that the number 2 carbon's hydrogens and the ethyl group's number 1 carbon's hydrogens are the same and equally likely to get hit as the number 4 carbon's hydrogens. So if all 3 carbons get hit equally then 2/3rds of the product will be what kaplan shows as the major product and 1/3rd will be what they show as the minor. personally i think theyre right.