Question: (a) On being heated with potassium ethoxide in ethanol (70C), the deuterium-labeled alkyl bromide shown gave a mixture of 1-butene, cis-2-butene, and trans-2-butene. On the

(a) On being heated with potassium ethoxide in ethanol (70°C), the deuterium-labeled alkyl bromide shown gave a mixture of 1-butene, cis-2-butene, and trans-2-butene. On the basis of your knowledge of the E2 mechanism, predict which alkene(s), if any, contained deuterium.

(b) The bromide shown in part (a) is the erythro diastereomer. How would the deuterium content of the alkenes formed by dehydrohalogenation of the threo diastereomer differ from those produced in part (a)?

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a The E2 transition state requires that the bromine and the hydrogen that is lost be anti periplanar ... View full answer

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