Suggested solution whether the first reaction is e1

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Unformatted text preview: Chapter 17 – Elimination Reactions PROBLEM 3 Suggest mechanisms for these eliminations. Why does the first give a mixture and the second a single product? H3PO4 + heat 64% yield, 4:1 ratio OH OH 48% HBr heat OH Purpose of the problem Regioselectivity of eliminations. Suggested solution Whether the first reaction is E1 or E2, there are two sets of hydrogen atoms that could be lost in the elimination. The conditions suggest E1 and the major product may be so because of equilibration. H + H OH OH2 The second reaction produces a more stable tertiary cation from which any of six protons could be lost, but all give...
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