destroyer orgo # 28

[Mstoothlady2012]

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For # 28 - on the second step why wouldn't it form the double bond on the ring so that the carbons carrying the double bond are secondary and tertiary? If you follow that then you would get E as the answer not B. Thanks!🙂

 

[Orgodox]

The reason is because the base it big and bulky which give the hoffman product (less substituted) since it is to sterically hindered it cant "dig in" to form the more substituted one so takes a more accessible Hydrogen

 

[Mstoothlady2012]

The reason is because the base it big and bulky which give the hoffman product (less substituted) since it is to sterically hindered it cant "dig in" to form the more substituted one so takes a more accessible Hydrogen

oh! makes sense...Thanks!