The commercial synthesis of a useful heterocyclic derivative requires treatment ofa
Chapter 25, Problem 57(choose chapter or problem)
The commercial synthesis of a useful heterocyclic derivative requires treatment ofa mixture of aldopentoses (derived from corncobs, straw, etc.) with hot acid under dehydratingconditions. The product, E, has 1H NMR spectrum E, shows a strong IR band at 1670 cm21, and isformed in nearly quantitative yield. Identify compound E and formulate a mechanism for itsformation.9.5 9.0 8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 0.0E(CH3)4Si300-MHz 1H NMR spectrum ppm ()9.6 9.5 7.6 7.2 7.1 6.51 H1 H1 H1 H1H NMRP r o b l e m s1208 Chapter 2 5 H e t e r o c y c l e sAldopentoses uuy C5H4O2Compound E is a valuable synthetic starting material. The following sequence convertsit into furethonium, which is useful in the treatment of glaucoma. What is the structure offurethonium?E uuuuuuuuuy furethonium
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