As we will learn in Chapter 21, treating a lactone (a cyclic ester) with sodium

Chapter 3, Problem 3.30

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As we will learn in Chapter 21, treating a lactone (a cyclic ester) with sodium hydroxide will initially produce an anion: NaOH Initially formed O O O O H O @ This anion rapidly undergoes an intramolecular proton transfer (see 3.3), in which the negatively charged oxygen atom abstracts the nearby acidic proton. Draw the product of this intramolecular acid-base process and then identify which side of the equilibrium is favored. Explain your answer.

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