As we will learn in Chapter 9, an epoxide is an ether with an oxygen atom in a
Chapter 7, Problem 7.87(choose chapter or problem)
As we will learn in Chapter 9, an epoxide is an ether with an oxygen atom in a three-membered ring. Epoxides can be made by intramolecular SN2 reactions of intermediates that contain a nucleophile and a leaving group on adjacent carbons, as shown. SN2 base C HO H H H H Br C intramolecular H H H H epoxide C O C C O H H H H Br C + Br Assume that each of the following starting materials can be converted to an epoxide by this reaction. Draw the product formed (including stereochemistry) from each starting material. Why might some of these reactions be more diffi cult than others in yielding nucleophilic substitution products? a. (CH3)3C OH Br b. (CH3)3C OH Br c. (CH3)3C OH Br d. (CH3)3C OH Br
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