DAT destroyer Ochem question

[santal907]

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#28 and 80
Since there is a strong bulky base, (CH3)3COH, in the step 2), should it have E2 and make a double bond in the more subs area?

 

[shoombol tallah]

No. Big bulky bases like K+ t-butoxide make a double bond at the least substituted c-c bond as in number 28 (forming methylene cyclohexane). In order for it to form the more substituted alkene a strong base non-bulky base like CH3CH2O-/CH3CH2OH would have to be used. Same goes for number 80. Big bulky base forms Hoffman (least substituted) small base forms Zaitzev alkene (most substituted). Hope that helps

 

[santal907]

Thanks!