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- Rank the attached compounds in order of increasing wavenumber of the carbonyl absorption in the IR.Predicting the Relative Position of Carbonyl Absorptions Rank compounds A, B, and C in order of increasing frequency of the carbonyl absorption in their IR spectra.Consider the para-substituted aromatic ketones, NO2C6H4COCH3 (p-nitroacetophenone) and CH3OC6H4COCH3 (p-methoxyacetophenone).a. Which carbonyl compound is more stable?b. Which compound forms the higher percentage of hydrate at equilibrium?c. Which compound exhibits a carbonyl absorption at higher wavenumber in its IR spectrum? Explain your reasoning ineach part.
- Explain why the β carbon of an α,β-unsaturated carbonyl compound absorbs farther downfield in the 13C NMR spectrum than the α carbon, even though the α carbon is closer to the electron-withdrawing carbonyl group. For example, the β carbon of mesityl oxide absorbs at 150.5 ppm, whereas the α carbon absorbs at 122.5 ppm.Explain why the β carbon of an α,β-unsaturated carbonyl compound absorbs farther downeld in the 13C NMR spectrum than the α carbon, even though the α carbon is closer to the electron-withdrawing carbonyl group. For example, the β carbon of mesityl oxide absorbs at 150.5 ppm, while the α carbon absorbs at 122.5 ppm.The 1H NMR spectrum of bullvalene at 100 C consists only of a single peak at 4.22 . Explain.
- Rank the following compounds in order of increasing frequency of the carbonyl absorption.Explain why the pKa of compound A is lower than the pKa's of bothcompounds B and C.Explain why the β carbon of an α,β-unsaturated carbonyl compound absorbs farther downfield in the 13 C NMR spectrum than the α carbon, even though the α carbon is closer to the electron-withdrawing carbonyl group. For example, the β carbon of mesityl oxide absorbs at 150.5 ppm, while the α carbon absorbs at 122.5 ppm.
- Estrone is a female sex hormone, and etonogestrel is a synthetichormone used in contraceptive implants to prevent pregnancy. (a)Identify the prominent IR absorptions resulting from the functionalgroups in each compound. (b) How do the locations of the carbonylabsorptions in these two compounds compare? Explain your reasoning.Which of the diethylbenzene isomers (ortho, meta, or para) correspondsto each set of 13C NMR spectral data ? 13C NMR signals: 16, 29, 128, and 141 ppmAn unknown compound A (molecular formula C7H14O) was treated withNaBH4 in CH3OH to form compound B (molecular formula C7H16O).Compound A has a strong absorption in its IR spectrum at 1716 cm−1.Compound B has a strong absorption in its IR spectrum at 3600−3200cm−1. The 1H NMR spectra of A and B are given. What are the structuresof A and B?