22. Carboxylic Acid Derivatives: NAS

Which of the following compounds will decarboxylate when heated?

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(••••) LOOKING AHEAD In Chapter 19, we will learn about the hydrolysis of t-butyl esters. In the reaction below, the hydrolysis is coupled to the decarboxylation reaction learned in this chapter. Suggest a mechanism for this reaction. [Hint: The formation of t-butanol proceeds by an SN1 reaction.]

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(••••) LOOKING AHEAD While acidic conditions were used in Assessment 18.68, decarboxylation of esters can also be conducted under basic conditions to give, at least temporarily, the enolate product shown. [We’ll learn more about the chemistry of enolates in Chapter 20.] Suggest a mechanism of this reaction. [Hint: The formation of chloromethane proceeds by an SN2 reaction.]

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