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Organic Chemistry
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- Propose a structural formula for the analgesic phenacetin, molecular formula C10H13NO2, based on its 1H-NMR spectrum.arrow_forwardCompound A, a hydrocarbon with M+=96 in its mass spectrum, has the 13C spectral data given below. On reaction with BH3, followed by treatment with basic H2O2. A is converted into B, whose, 13C spectral data are also given below. Propose structures for A and B. Compound A Broadband-decoupled l3C NMR: 26.8, 28.7, 35.7, 106.9, 149.7 DEPT-90: no peaks DEPT-135: no positive peaks; negative peaks at 26.8, 28.7, 35.7, 106.9 Compound B Broadband-decoupled 13C NMR: 26.1, 26.9, 29.9, 40.5, 68.2 DEPT-90: 40.5 DEPT-135: positive peak at 40.5 ; negative peaks at 26.1, 26.9. 29.9, 68.2arrow_forward21arrow_forward
- A compound (L) with the molecular formula C9H10 reacts with bromine and gives an IR absorption spectrum that includes the following absorption peaks: 3035 cm ¹(m), 3020 cm ¹(m), 2925 cm ¹(m), 2853 cm ¹(w), 1640 cm ¹1(m), 990 cm ¹(s), 915 cm ¹(s), 740 cm ¹(s), 695 cm ¹(s). The ¹H NMR spectrum of L consists of: Doublet 3.1 ppm (2H) Multiplet 5.1 ppm Multiplet 7.1 (5H) ppm Multiplet 4.8 ppm Multiplet 5.8 ppm The UV spectrum shows a maximum at 255 nm. Propose a structure for compound L. Edit Drawing harrow_forwardThe 'H NMR spectrum of compound A (C3H100) has four signals: a multiplet at 8 = 7.25-7.32 ppm (5 H), a singlet at d = 5.17 ppm (1 H), a quartet at d = 4.98 ppm (1 H), and a doublet at ô = 1.49 ppm (3 H). There are 6 signals in its 13C NMR spectrum. The IR spectrum has a broad absorption in the -3200 cm-1 region. Compound A reacts with KMNO4 in a basic solution followed by acidification to give compound B with the molecular formula C7H6O2. Draw structures for compounds A and B.arrow_forwardThe mass spectrum of 1-ethyl-1-methylcyclohexane shows many fragments, with two in very large abundance. One appears at m/z = 111 and the other appears at m/z = 97. Determine the identity and structure of each of these fragmentsarrow_forward
- The 1H-NMR spectrum of compound R, C6H14O, consists of two signals: d 1.1 (doublet) and d 3.6 (septet) in the ratio 6:1. Propose a structural formula for compound R consistent with this informationarrow_forwardMass spectrometry of an unknown compound revealed a molecular ion at m/z 100.09. The IR spectrum, the ¹³C NMR spectrum, and the ¹H NMR spectrum are shown below. Draw the structure of this compound. 4000 220 3000 200 180 160 2000 M 1500 Wavenumbers (cm-¹) 140 120 100 1H 80 6H 1000 40 3H 20 ppm 500arrow_forwardDetermine the most likely structure of a compound with the formula C9H12 if it gave an H NMR spectrum consisting of: A doublet at d 1.25, a septet at d 2.90 and a multiplex at d 7.25arrow_forward
- Propose a structure for a compound of molecular formula C,H1402 with an IR absorption at 1740 cm and the following 'H NMR data: Absorption ppm Relative Area singlet 1.2 9 triplet 1.3 3 quartet 4.1arrow_forwardThe infiared spectrum of a compound contains a strong absorption at 1702 cm-1. The mass spectrum of the compound is shown below. What is the structure of the compound? 100 10 50 70 m/z 80 100 110 120 Relative Intensityarrow_forwardThe mass spectrum of an aldehyde shows a parent peak at m/z = 58 and a base peak at m/z = 29. Propose a structure, and identify the two species whose m/z values were listed. Name the compound in the box below.arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning