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Two compounds with the molecular formula
(a)
(b)
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Organic Chemistry
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Organic Chemistry As a Second Language: Second Semester Topics
- Propose a structural formula for the analgesic phenacetin, molecular formula C10H13NO2, based on its 1H-NMR spectrum.arrow_forwardThe following 1H NMR spectra are for four compounds, each with molecular formula of C6H12O2. Identify the compounds.arrow_forwardAn aromatic compound K, whose molecular formula is C8H11N, is examined in the laboratory to elucidate its structure. The following observations were made: A) Compound K is soluble in dilute hydrochloric acid but insoluble in sodium hydroxide solution. B) Treatment of compound K with excess potassium hydroxide and benzenesulfonyl chloride, C(6)H(5)SO(2)Cl, results in the formation of a heterogeneous mixture. The NMR spectrum of compound K is shown below. C) Compound K when treated with acetic anhydride[CH3-C(O)-O-C(O)-CH3], gives compound L, whose molecular formula is C(10)H(13)ON. Compound L is insoluble in dilute acid or dilute base at room temperature, heating compound L in dilute acid or base, however, regenerates compound K. D) When compound L is heated with a mixture of concentrated nitric acid and sulfuric acid, a single product, compound M, with the molecular formula C(10)H(12)O(3)N(2) is formed in excellent yields. On the basis of these observations draw the structures of…arrow_forward
- Compound A, C8H10O, has the IR and 1H NMR spectra shown. Propose a structure consistent with the observed spectra, and label each peak in the NMR spectrum. Note that the absorption at 5.5 î disappears when D2O is added.arrow_forwardTwo compounds with the molecular formula C5H10O have the following 1H and 13C NMR data. Both compounds have a strong IR absorption band in the 1710–1740-cm_1 region. Elucidate the structure of these two compounds and interpret the spectra. (10) (a) 1H NMR: d 2.55 (septet, 1H), 2.10 (singlet, 3H), 1.05 (doublet, 6H); 13C NMR: d 212.6, 41.5, 27.2, 17.8 (b) 1H NMR: d 2.38 (triplet, 2H), 2.10 (singlet, 3H), 1.57 (sextet, 2H), 0.88 (triplet, 3H); 13C NMR: d 209.0, 45.5, 29.5, 17.0, 13.2arrow_forwardFrom the following 1H-NMR and 13C-NMR spectra, assign a structure for a compound with a formula of C4H9Br:arrow_forward
- Phenacetin is an analgesic compound having molecular formula C10H13NO2. Once a common component in over-the-counter pain relievers such as APC (aspirin, phenacetin, caffeine), phenacetin is no longer used because of its liver toxicity. Deduce the structure of phenacetin from its 1H NMR and IR spectra.arrow_forwardThere are several isomeric alkanes of molecular formula C6H14.Two of these exhibit the following 1H-NMR spectra. Propose a structure for each of the isomers. Isomer A: δ = 0.84 (d, 12 H), 1.39 (septet, 2H) ppm Isomer B: δ = 0.84 (t, 3 H), 0.86 (s, 9H), 1.22 (q, 2H) ppmarrow_forwardCompound K, molecular formula C6H14O, readily undergoes acid-catalyzed dehydration when warmed with phosphoric acid to give compound L, molecular formula C6H12, as the major organic product. The 1H-NMR spectrum of compound K shows signals at d 0.90 (t, 6H), 1.12 (s, 3H), 1.38 (s, 1H), and 1.48 (q, 4H). The 13C-NMR spectrum of compound K shows signals at d 72.98, 33.72, 25.85, and 8.16. Deduce the structural formulas of compounds K and L.arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning