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- Ibufenac, a para-disubstituted arene with the structureHO2CCH2C6H4CH2CH(CH3)2 , is a much more potent analgesic thanaspirin, but it was never sold commercially because it caused livertoxicity in some clinical trials. Devise a synthesis of ibufenac frombenzene and organic halides having fewer than five carbons.Name and Draw the Phenolof all possible chemical (Electrophilic aromatic substitution) reactions of the compound namely; Halogenation (Chlorination or Bromination) NitrationDescribe a sequence of reactions for the following reaction
- Ibufenac, a para-disubstituted arene with the structure HO2CCH2C6H4CH2CH(CH3)2, is a much more potent analgesic than aspirin, but it was never sold commercially because it caused liver toxicity in some clinical trials. Devise a synthesis of ibufenac from benzene and organic halides having fewer than five carbons.Show how enols, enamines, and enolate ions act as nucleophiles. Give mechanismsfor acid-catalyzed and base-catalyzed keto–enol tautomerisms.What is the major product of the following ozonolysis reaction? and and HO
- Provide a plausible arrow pushing mechanism for the reaction below. 1 eq. H20 HO MEOH OMe cat. H-A OHProblem 19.22 Show how ethyl bromide can be used as a starting material in the preparation of each of the following compounds. (Hint: How are Grignard reagents prepared?) HO `CH;CH3 (a) OH (b) OH (c) 1-butanol (d) PHCHCH,CH; (CH;CH;),CCH3The key step in a reported laboratory synthesis of sativene, a hydrocarbon isolated from the mold Helminthosporium sativum, involves the following base treatment of a keto tosylate. What kind of reaction is occurring? How would you complete the synthesis?
- As far back as the 16th century, South American Incas chewed the leaves of the coca bush, Erythroxylon coca, to combat fatigue. Chemical studies of Erythroxylon coca by Friedrich Wöhler in 1862 resulted in the discovery of cocaine, C17H21NO4, as the active component. Basic hydrolysis of cocaine leads to methanol, benzoic acid, and another compound called ecgonine, C9H15NO3. Oxidation of ecgonine with CrO3 yields a keto acid that readily loses CO2 on heating, giving tropinone. (a) What is a likely structure for the keto acid? (b) What is a likely structure for ecgonine, neglecting stereochemistry? (c) What is a likely structure for cocaine, neglecting stereochemistry?Name and Draw the structures of all possible chemical (Electrophilic aromatic substitution) reactions of the Phenolcompound namely; Halogenation (Chlorination or Bromination)w how enols, enolate ions, andenamines act as nucleophiles. Predictthe products of their reactions withhalogens, alkyl halides, and otherelectrophiles. Show how they areuseful in synthesis.
