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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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Chapter 13 Solutions
Organic Chemistry
- Propose a structural formula for the analgesic phenacetin, molecular formula C10H13NO2, based on its 1H-NMR spectrum.arrow_forwardCompound P has molecular formula C5H9ClO2. Deduce the structure of P from its 1H and 13C NMR spectra.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
- An unknown compound D exhibits a strong absorption in its IR spectrumat 1692 cm−1. The mass spectrum of D shows a molecular ion at m/z =150 and a base peak at 121. The 1H NMR spectrum of D is shown below.What is the structure of D?arrow_forwardDraw the compound.arrow_forwardGiven here are 1H-NMR and 13C-NMR spectral data for nine compounds. Each compound shows strong absorption between 1720 and 1700 cm-1 and strong, broad absorption over the region 2500–3300 cm-1. Propose a structural formula for each compound.arrow_forward
- Compound P has molecular formula C5H9ClO2. Deduce the structure of Pfrom its 1H and 13C NMR spectra.arrow_forwardPropose a structure for a compound, C10H14, that fits the following 1H NMR data. δ1.30, 9H, singlet δ7.30, 5H, singletarrow_forwardThe 1H-NMR spectrum of Compound C shows five signals – δ 2.38 (1H, dt), 2.72 (1H, dt), 5.34 (1H, t), 5.49 (2H, ddd), 6.27 (2H, dd) ppm. Its 13C-NMR spectrum has four signals – δ 26, 58, 127, 129 ppm. In the compound’s mass spectrum, the M+1 peak appears at m/z = 115. An M+2 peak, whose intensity is roughly one-third that of the M+1 peak, also appears. Suggest a structure for this compound.arrow_forward
- Given 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_forwardCompound 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_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_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning
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