Concept explainers
Interpretation:
The molecular formula and the structure of an unknown compound to be predicted using spectrum details.
Concept introduction:
Molecular formula:
It represents the types of atoms with their total number present in a given molecule.
The 13CNMR spectrum gives information on the different electronic environments of carbon. As like 1HNMR, the number of signals generated in 13CNMR are predicted by performing symmetry operations (rotation or reflection symmetry). Only chemical shift values are reported in the spectrum but not the multiplicity and integration values because the coupling between two neighboring 13C-13 C nuclei are weakly involved due to the low abundance of 13C isotopes of carbon atom.
To identify: The structure to be predicted for C5H10O.
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Organic Chemistry
- 3-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_forwardPropose a structural formula for the analgesic phenacetin, molecular formula C10H13NO2, based on its 1H-NMR spectrum.arrow_forward15. Propose a structure for a compound, C6H₁40, with the following ¹3C NMR spectral data: Broadband decoupled ¹3C NMR: 23.0, 68.4 S DEPT-90: 68.4 8 DEPT-135: positive peaks at 23.0, 68.4 ; no negative peaksarrow_forward
- Propose a structure for a compound, C10H14, that fits the following 1H NMR data. δ1.30, 9H, singlet δ7.30, 5H, singletarrow_forwardPropose a structure that is consistent with each set of 1H-NMR data. a) C5H10O 13C –NMR shows 4 types of C d 9.7, s, 1H d 2.3, d, 2H d 2.2, m, 1H d 1.0, d, 6H b) C4H8O2 13C-NMR shows one signal. & 3.8, s, 8Harrow_forwardGiven the following 13C NMR signals, construct a structure for the unknown compounds. A. Molecular formula: C6H14O DEPT-135 (positive): 14.1 δ DEPT-135 (negative): 22.7 δ, 25.3 δ, 31.8 δ, 32.2 δ, 62.8 δ B. Molecular formula: C7H12O2 Broadband decoupled: 19.1 δ, 28.0 δ, 70.5 δ, 129.0 δ, 129.8 δ, 165.8 δ DEPT-90: 28.0 δ, 129.8 δ DEPT-135 (positive): 19.1 δ, 28.0 δ, 129.8 δ DEPT-135 (negative): 70.5 δ, 129.0 δarrow_forward
- Compound X (molecular formula C10H120) was treated with NH2NH2, ¯OH to yield compound Y (molecular formula C10H14). Match the 1H NMR spectra of X and Y to the corresponding structures of X and Y. Compound NH2NH2 Compound 'H NMR of X 6 H OH Y 1 H 5H 8. 6. 4 ppm or H NMR of Y 6 H 2H 5H 1 H multiplet multiplet 8. 6. 4. 3. 1 nnm 2. 2. 3, O:arrow_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_forwardGiven the following 13C NMR signals, construct a structure for the unknown compounds. A. Molecular formula: C4H10O Broadband decoupled: 69.3 δ, 32.1 δ, 22.8 δ, 10.0 δ DEPT-90: 69.3 δ DEPT-135 (positive): 69.3 δ, 22. 8 δ, and 10.0 δ DEPT-135 (negative): 32.1 δ B. Molecular formula: C6H14O DEPT-135 (positive): 14.1 δ DEPT-135 (negative): 22.7 δ, 25.3 δ, 31.8 δ, 32.2 δ, 62.8 δ C. Molecular formula: C7H12O2 Broadband decoupled: 19.1 δ, 28.0 δ, 70.5 δ, 129.0 δ, 129.8 δ, 165.8 δ DEPT-90: 28.0 δ, 129.8 δ DEPT-135 (positive): 19.1 δ, 28.0 δ, 129.8 δ DEPT-135 (negative): 70.5 δ, 129.0 δarrow_forward
- The 1H-NMR spectrum of Compound D of molecular formula C10H12O shows three singlets – δ 2.20 (6H, s), 4.86 (4H), 7.10 (2H) ppm. Its 13C-NMR spectrum has five signals – 20, 74, 127, 135, 146 ppm. Suggest a structure for this compound.arrow_forwardDeduce the structure of a compound with molecular formula C5H100 that exhibits the following ¹H and ¹³C NMR spectra. IH NMR CNMR 150 10 Structure A Structure B Structure C Structure D 24 1C 100 B 2H H 20 50 10 D 311arrow_forwardWhich compound is best represented by the 1H NMR spectra shown here? 1.06 ppm (d), 12 2.70 ppm (m), 2 PPM o A O B O D O E o G H Ooo oooOarrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning