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Chapter 14 Solutions
Organic Chemistry
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Chemistry: Structure and Properties
Basic Chemistry
Chemistry: Atoms First
- Compound H (C8H6O3) gives a precipitate when treated with hydroxylamine in aqueous ethanol and a silver mirror when treated with Tollens solution. Following is its 1H-NMR spectrum. Deduce the structure of compound H.arrow_forwardCompound I (C11H14O2) is insoluble in water, aqueous acid, and aqueous NaHCO3, but dissolves readily in 10% Na2CO3 and 10% NaOH. When these alkaline solutions are acidified with 10% HCl, compound I is recovered unchanged. Given this information and its 1H-NMR spectrum, deduce the structure of compound I.arrow_forwardAnethole, C10H12O, a major constituent of the oil of anise, has the 1H NMR spectrum shown. On oxidation with Na2Cr2O7, anethole yields p-methoxybenzoic acid. What is the structure of anethole? Assign all peaks in the NMR spectrum, and account for the observed splitting patterns.arrow_forward
- Propose a structural formula for the analgesic phenacetin, molecular formula C10H13NO2, based on its 1H-NMR spectrum.arrow_forwardPhenacetin, a substance formerly used in over-the-counter headache remedies, has the formula C10H13NO2. Phenacetin is neutral and does not dissolve in either acid or base. When warmed with aqueous NaOH, phenacetin yields an amine, C8H11NO, whose 1H NMR spectrum is shown. When heated with HI, the amine is cleaved to an aminophenol, C6H7NO. What is the structure of phenacetin, and what are the structures of the amine and the aminophenol?arrow_forward3-Chlorocyclopropene, on treatment with AgBF4, gives a precipitate of AgCl and a stable solution of a product that shows a single 1H NMR absorption at 11.04 δ. What is a likely structure for the products, and what is its relation to HĂ¼ckel’s rule?arrow_forward
- Reaction of p-cresol with two equivalents of 2-methylprop-1-ene affordsBHT, a preservative with molecular formula C15H24O. BHT gives thefollowing 1H NMR spectral data: 1.4 (singlet, 18 H), 2.27 (singlet, 3 H), 5.0(singlet, 1 H), and 7.0 (singlet, 2 H) ppm. What is the structure of BHT?Draw a stepwise mechanism illustrating how it is formed.arrow_forwardWhen heated with chromic acid, compound A forms benzoic acid. Identify compound A from its 1H NMR spectrum.arrow_forwardWhen a compound with molecular formula C11H14O2 undergoes acid-catalyzed hydrolysis, one of the products that is isolated gives the following 1H NMR spectrum. Identify the compound.arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning