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Which of the following reagents is most appropriate to selectively convert 2-bromo-2,3-dimethylbutane into 2,3-dimethylbut-1-ene as the major product?

Options

  1. ASodium ethoxide in ethanol
  2. BAqueous potassium hydroxide
  3. CEthanolic silver cyanide
  4. DPotassium tert-butoxide in tert-butyl alcohol

Correct answer

D. Potassium tert-butoxide in tert-butyl alcohol

Step-by-step solution

The substrate, 2-bromo-2,3-dimethylbutane, is a tertiary alkyl halide. Elimination can occur at two different -positions to give either 2,3-dimethylbut-2-ene (the more substituted Saytzeff product) or 2,3-dimethylbut-1-ene (the less substituted Hofmann product). The desired major product is 2,3-dimethylbut-1-ene, which is the Hofmann product. To reverse the normal regioselectivity and favor the formation of the less substituted alkene, a sterically bulky strong base must be used. Potassium tert-butoxide is a bulky

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