Many furan derivatives are unstable in strong acid. Hydrolysis of 2,5-dimethylfuran in
Chapter 26, Problem 26.39(choose chapter or problem)
Many furan derivatives are unstable in strong acid. Hydrolysis of 2,5-dimethylfuran in aqueous acid gives a compound A, C6H10O2, that has a proton NMR spectrum consisting entirely of two singlets at d 2.1 and d 2.6 in the ratio 3 : 2, respectively. On treatment of compound A with very dilute NaOD in D2O, both NMR signals disappear. Treatment of A with zinc amalgam and HCl gives hexane. Propose a structure for A, and then give a curved-arrow mechanism for its formation from 2,5-dimethylfuran.
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