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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- Compound 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_forwardAs reaction of (CH3)2CO with LIC≡CH followed by H2O affords compound D, which has a molecular ion in its mass spectrum at 84 and prominent absorptions in its IR spectrum at 3600−3200, 3303, 2938, and 2120 cm−1. D shows the following 1H NMR spectral data: 1.53 (singlet, 6 H), 2.37 (singlet, 1 H), and 2.43 (singlet, 1 H) ppm. What is the structure of D?arrow_forwardPropose a structure for a compound, C10H14, that fits the following 1H NMR data. δ1.30, 9H, singlet δ7.30, 5H, singletarrow_forward
- A compound has a molecular formula of C8H8O The following spectra (1H NMR, Carbon 13 NMR, IR was collected. Give a possible structure. 13C NMR – 8 peaksarrow_forwardAddition of m-xylene to the strongly acidic solvent HF/SbF5 at -45°C gives a new species, which shows 1H-NMR resonances at d 2.88 (3H), 3.00 (3H), 4.67 (2H), 7.93 (1H), 7.83 (1H), and 8.68 (1H). Assign a structure to the species giving this spectrum.arrow_forwardPropose a structure consistent with following set of spectral data: C5H10O2: IR peak at 1740 cm−1; NMR (ppm): 1.15 (triplet, 3 H) 2.30 (quartet, 2 H) 1.25 (triplet, 3 H) 4.72 (quartet, 2 H)arrow_forward
- Compound B of molecular formula C9H19N shows a noteworthy infrared absorption at 3300 cm-1. Its 1H-NMR spectrum shows three singlets – δ 1.0 (6H), 1.1 (12H), 1.4 (1H) ppm. Its 13C-NMR spectrum has four signals – δ 25, 28, 41, 64 ppm. Suggest a structure for this compound. Please show work.arrow_forwardCompound A, MW 86, shows an IR absorption at 1730 cm-1 and a very simple 1H NMR spectrum with peaks at 9.7 (1 H, singlet) and 1.2 (9 H, singlet). Propose a structure for A.arrow_forwardPropose a structure consistent with the following spectral data for a compound C8H18O2: IR: 3350 cm-1 1H NMR: 1.24 δ (12 H, singlet); 1.56 δ (4 H, singlet); 1.95 δ (2 H, singlet)arrow_forward
- 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_forwardAddition of m-xylene to the strongly acidic solvent HF/SbF5 at 45C gives a new species, which shows 1H-NMR resonances at 2.88 (3H), 3.00 (3H), 4.67 (2H), 7.93 (1H), 7.83 (1H), and 8.68 (1H). Assign a structure to the species giving this spectrum.arrow_forwardAcidcatalyzed dehydration of 3hydroxy3phenylcyclohexanone leads to an unsaturated ketone. What possible structures are there for the product? At what position in the ER spectrum would you expect each to absorb? If the actual product has an absorption at 1670 cm-1, what is its structure?arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning