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- Draw a stepwise mechanism for the reduction of epoxide A to alcohol B using LiAlH4. What product would be formed if LiAlD4 were used as reagent? Indicate the stereochemistry of all stereogenic centers in the product using wedges and dashed wedges.Draw the major organic product when this compound is treated with NBS and heat: H3C -CH3PROBLEM 4.13 Write the structures of all the alkenes that can be formed by dehydrohalogenation of each of the following alkyl halides. Apply the Zaitsev rule to predict the alkene formed in greatest amount in each case. (a) 2-Bromo-2,3-dimethylbutane (c) 3-Bromo-3-ethylpentane (b) tert-Butyl chloride (d) 2-Bromo-3-methylbutane