Chapter 22: Problem 31
Propose a synthesis of \(1,3,5\) -tribromobenzene from benzene.
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Chapter 22: Problem 31
Propose a synthesis of \(1,3,5\) -tribromobenzene from benzene.
These are the key concepts you need to understand to accurately answer the question.
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Triphenylmethyl radical, \(\left(\mathrm{C}_{6} \mathrm{H}_{5}\right)_{3} \mathrm{C} \cdot\), is stable at room temperature in dilute solution in an inert solvent, and salts of triphenylmethyl cation, \(\left(\mathrm{C}_{6} \mathrm{H}_{5}\right)_{3} \mathrm{C}^{+}\), can be isolated as stable crystalline solids. Propose explanations for the unusual stabilities of these species.
Hexachlorophene (margin) is a skin germicide formerly used in soaps. It is prepared in one step from \(2,4,5\) -trichlorophenol and formaldehyde in the presence of sulfuric acid. How does this reaction proceed? (Hint: Formulate an acid-catalyzed hydroxymethylation for the first step.)
Starting with benzenamine, propose a synthesis of aklomide, an agent used to treat certain exotic fungal and protozoal infections in veterinary medicine. Several intermediates are shown to give you the general route. Fill in the blanks that remain; each requires as many as three sequential reactions. (Hint: Review the oxidation of amino- to nitroarenes in Section \(16-5 .\) )
Propose syntheses of each of the following compounds, beginning in each case with ethylbenzene. (a) (1-Chloroethyl)benzene; (b) 2 -phenylpropanoic acid; (c) 2-phenylethanol; (d) 2-phenyloxacyclopropane.
Phenylmethanol (benzyl alcohol) is converted into (chloromethyl)benzene in the presence of hydrogen chloride much more rapidly than ethanol is converted into chloroethane. Explain.
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