Although -butyrolactone ( 19.63) is a biologically inactive compound, it is converted in

Chapter 22, Problem 22.59

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Although -butyrolactone ( 19.63) is a biologically inactive compound, it is converted in the body to 4-hydroxybutanoic acid (GHB), an addictive and intoxicating recreational drug (Section 19.5). Draw a stepwise mechanism for this conversion in the presence of acid. O O HO OH H3O+ O -butyrolactone 4-hydroxybutanoic acid GHB

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