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Treatment of compound E (molecular formula
Compound E signals at
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Chapter 20 Solutions
ORGANIC CHEMISTRY
- Compound P has molecular formula C5H9ClO2. Deduce the structure of P from its 1H and 13C NMR spectra.arrow_forwardCompound A of molecular formula C3H6O shows a noteworthy infrared absorption at 1716 cm-1. Its 1H-NMR spectrum shows one singlet – δ 2.2 (6H) ppm. Its 13C-NMR spectrum has two signals – δ 30, 207 ppm. Suggest a structure for this compound.arrow_forwardIdentify the structure of compound C (molecular formula C11H15NO2), which has an IR absorption at 1699 cm−1 and the 1H NMR spectrum shown below.arrow_forward
- Compound X (molecular formula C10H12O) was treated with NH2NH2, −OH to yield compound Y (molecular formula C10H14). Based on the 1HNMR spectra of X and Y given below, what are the structures of X and Y?arrow_forwardAn unknown compound A has the molecular formula C4H8O2. Based on the following 1H NMR spectrum, what is the structure of compound A?arrow_forwardAn unknown compound C of molecular formula C6H12O3 exhibits a strong absorption in its IR spectrum at 1718 cm−1 and the given 1H NMR spectrum. What is the structure of C?arrow_forward
- Identify the structure of compound C (molecular formula C11H15NO2), which has an IR absorption at 1699 cm−1 and the 1H NMR spectrum shown below.arrow_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_forwardCompound A is treated with a mixture of nitric and sulfuric acids to generate Compound B. The 1H-NMR spectrum of B shows two singlets, one at 2.52 pm and one at 8.13 ppm. The 13C-NMR spectrum of B shows five signals. The mass spectrum of B shows a peak at m/z = 260 and another peak at m/z = 262; the relative height of the two peaks is 1:1 respectively. - Identify compound B, explaining your reasoningarrow_forward
- Propose a structure of compound C (molecular formula C10H12O) consistent with the following data. C is partly responsible for the odor and flavor of raspberries. Compound C: IR absorption at 1717 cm–1arrow_forwardTreatment of compound E (molecular formula C4H8O2) with excess CH3CH2MgBr yields compound F (molecular formula C6H14O) after protonation with H2O. E shows a strong absorption in its IR spectrum at 1743 cm-1. F shows a strong IR absorption at 3600–3200 cm-1. The 1H NMR spectral data of E and F are given. What are the structures of E and F?Compound E signals at 1.2 (triplet, 3 H), 2.0 (singlet, 3 H), and 4.1 (quartet, 2 H) ppmCompound F signals at 0.9 (triplet, 6 H), 1.1 (singlet, 3 H), 1.5 (quartet, 4 H), and 1.55 (singlet, 1 H) ppmarrow_forwardIdentify products A and B from the given 1H NMR data. Treatment of acetone [(CH3)2C=O] with dilute aqueous base forms B. Compound B exhibits four singlets in its 1H NMR spectrum at 1.3 (6 H), 2.2 (3 H), 2.5 (2 H), and 3.8 (1H) ppm. What is the structure of B?arrow_forward
Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning