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2. Write reasonable detailed mechanisms for the following reactions. a) OH OH H3PO4 OH b) O H 1) NH2OH, H+ / N 2) H2SO4 3. 1900 cm-1. This compound decomposed rapidly to a four-membered ring lactone detailed could a) The epoxidation of di-r-butyl ketene, gave an unstable compound with an IR stretch that at be securely . identified. Propose a structure for the unstable compound formed, and a mechanism for its subsequent transformation to the final lactone shown. mCPBA H+ O c=c=0 ? O 4. Provide detailed mechanisms for the transformations shown below. a) OH H4 + O CO2H O b) Explain the striking observation that methylation of the alcohol shown leads to the methoxy compound in which the stereochemistry of the oxygen has changed. O O 1) NaH H 2) CH31 OMe OH H 5. this hydroxy-ketone with base followed by acid gives the enone shown. formed, What and Treatment is the structure of of intermediate compound A? Explain mechanistically how it is also provide the mechanism of its conversion to the final product. OH H2SO4 NaOH A heat O O

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