5. Bonus Question. Compound A has a chemical formula C3H1602. When A is refluxed in H20 and HCl, compound B (C6H120) and

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5 Bonus Question Compound A Has A Chemical Formula C3h1602 When A Is Refluxed In H20 And Hcl Compound B C6h120 And 1 (191.86 KiB) Viewed 78 times

5. Bonus Question. Compound A has a chemical formula C3H1602. When A is refluxed in H20 and HCl, compound B (C6H120) and ethylene glycol (HOCH2CH2OH) are formed. Compound B can react with NaBH4 in ethanol followed by aqueous workup to give a new liquid product C (C6H140). Compound C when treated with conc. H2SO4 under heat gives D (C6H12). Treatment of compound D with 03 followed by reductive workup with (CH3)2S yields two products E and F. Compounds E and F have the same chemical formula C3H60, and both of their IR spectra show a strong band at 1780 cm. The 13C NMR spectrum of E shows two signals, while three signals are observed in the 13C NMR spectrum of F. Propose the molecular structures for compounds A - F, and show the detailed reactions involved in the above chemical transformations. [10 pts]