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
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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What kinds of functional groups might compounds have if they show the following IR absorptions?
(a) Absorption at 1735 cm-1
(b) Absorption at 1810 cm-1
(c) Absorptions at 2500 to 3300 cm-1 and 1710 cm-1
(d) Absorption at 1715 cm-1
Write the mechanism of the reaction between p-hydroxyaniline and acetic anhydride to prepare acetaminophen.
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.
Show the mechanism of the following nucleophilic acyl substitution reaction, using curved arrows to indicate the electron flow in each step:

21-30 Electrostatic potential maps of a typical amide (acetamide) and an acyl azide (acetyl azide) are shown. Which of the two do you think is more reactive in nucleophilic acyl substitution reactions? Explain.

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