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The structure of thyroxine, a thyroid hormone that helps to regulate
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Organic Chemistry
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- 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.arrow_forwardMethamphetamine is a long-lasting, potent stimulant sold as a street drug. The synthesis is quite simple and one step in the synthesis is shown below. Using your knowledge of the reactions of amines, provide all the reagents necessary to complete the reaction below. Provide the reagents for step 1 and step 2 ,arrow_forwardThe compound eutypine is an antibacterial agent isolated from the fungus Eutypa lata. This fungus results in a disease common to vineyards called eutyposis. Give a sequence of reactions that will take the following reactant and give eutypine when the other reactants used in the sequence are acetylene and acetone.arrow_forward
- Propose a mechanism for the following reaction, an important step in the laboratory synthesis of proteins:arrow_forwardAcid-catalyzed hydrolysis of the following epoxide gives a trans diol. Of the two possible trans diols, only one is formed. How do you account for this stereoselectivity?arrow_forwardMinoxidil is a molecule that causes hair growth in some people. It was originally synthesized as a vasodilator for the treatment of hypertension (high blood pressure). Most of the patients taking the drug for hypertension were seen to grow body hair. Due to other side effects, its oral use was stopped, but it became popular as a topical cream to promote hair growth. The first key reaction in one synthesis of minoxidil follows. Draw the product of this reaction.arrow_forward
- Fluorination of a benzene ring can be accomplished with Selectfluor, a reagent that contains a fluorine bonded to a positively charged nitrogen atom. Fluorination is a useful reaction because several common drugs, such as the cholesterol-lowering drug atorvastatin, contain a fluorine bonded to an aromatic ring. Assuming that fluorination is analogous to other examples of electrophilic aromatic substitution, draw a stepwise mechanism for the following reaction.arrow_forwardBombykol, shown below, is a pheromone released by the female silkworm to attract males. Propose a synthesis of bombykol from acetylene.arrow_forward1 The aromatic heterocyclic base on quinoline (1 mole) is reacting with bromine (2 moles) and in presence of aluminum chloride. Which of the following statements about this reaction is correct?* Quinoline reacts more rapidly than benzene and is brominated at C-4 Quinoline reacts more slowly than benzene and is brominated at C-5 and C-8 Quinoline reacts more rapidly than benzene and is brominated at C-5 and C-8 Quinoline reacts more slowly than benzene and is brominated at C-3 and C-4 None of the abovearrow_forward
- Terreic acid, shown below, is a naturally occurring antibiotic metabolite of the fungus Aspergillus terreus. Terreic acid hinders bacterial growth by covalently binding to (and thereby deactivating) the biosynthetic enzyme MurA, which is responsible for synthesizing the bacterial cell wall. In aqueous environments, terreic acid tautomerizes to a more stable enol form. Draw the two most stable enol tautomers of terric acid. Circle the tautomer above that you would expect to predominate inside a cellular environment.arrow_forwardEthers, Epoxides and Thiols Proslem: Cleavage of cyclopentyl ethyl ether by HBr. ydroiodic acid (HI) reacts with ethers the same way HBr does. Aqueous iodide is a stronger nucleophile than aqueous bromide, and iodide reacts at a faster rate. We can rank the hydrohalic acids in order of their reactivity toward the cleavage of ethers: HI > HBr HCIarrow_forwardThe following three derivatives of succinimide are anticonvulsants that have found use in the treatment of epilepsy, particularly petit mal seizures. Q. Of these three anticonvulsants, one is considerably more acidic than the other two. Which is the most acidic compound? Estimate its pKa and account for its acidity. How does its acidity compare with that of phenol? with that of acetic acid?arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage LearningOrganic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage Learning
- EBK A SMALL SCALE APPROACH TO ORGANIC LChemistryISBN:9781305446021Author:LampmanPublisher:CENGAGE LEARNING - CONSIGNMENT