Chapter 21: Q71E (page 726)
21-71 Butacetin is an analgesic (pain-killing) agent that is synthesized commercially from p-fluoronitrobenzene. Propose a synthesis.
Short Answer
The synthesisis depicted below
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Chapter 21: Q71E (page 726)
21-71 Butacetin is an analgesic (pain-killing) agent that is synthesized commercially from p-fluoronitrobenzene. Propose a synthesis.
The synthesisis depicted below
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When an amide is formed from an acid chloride or an anhydride, two moles of base are required. However, when an ester is used as the starting material, only one equivalent of base is needed. Explain the reactivity in terms of basicity of the leaving groups.
21-75 One frequently used method for preparing methyl esters is by reactionof carboxylic acids with diazomethane,
The reaction occurs in two steps: (1) protonation of diazomethane bythe carboxylic acid to yield methyldiazonium ion,, plus a carboxylate ion; and (2) reaction of the carboxylate ion with .
(a) Draw two resonance structures of diazomethane, and account forstep 1.
(b) What kind of reaction occurs in step 2?
21-38 Treatment of an a-amino acid with DCC yields a 2,5-diketopiperazine.Propose a mechanism.

How might you prepare the following esters from the corresponding acids?

21-73 N,N-Diethyl-m-toluamide (DEET) is the active ingredient in manyinsect repellent preparations. How might you synthesize this substancefrom m-bromotoluene?
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