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- When diphenyl ether is reacted under the same conditions as in Problem 22.35, a compound is produced whose 13C NMR spectrum shows six signals. Draw that product.The 1H NMR spectrum of bullvalene at 100 C consists only of a single peak at 4.22 . Explain.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.
- 1. Predict the max. total number of possible peaks in the 1H NMR spectrum of episesamin a. Indicate the number of non-aromatic peaks in the 1H NMR of episesamin b. Indicate the number of aromatic peaks in the 1H NMR of episesaminYour organic chemistry study partner attempts the following reaction between a Grignard reagent and benzaldehyde. Unfortunately, your study partner does not form the desired product. Instead, a different product forms with the following 13C NMR signals: 73, 35, 23. Draw the desired product your study partner was trying to form.How many 1H NMR signals does attached natural product exhibit?
- 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.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.Reaction of unknown A with HCl forms chlorohydrin B as the major product. A shows no absorptions in its IR spectrum at 1700 cm−1 or 3600–3200 cm−1, and gives the following 1H NMR data: 1.4 (doublet, 3 H), 3.0 (quartet of doublets, 1 H), 3.5 (doublet, 1 H), 3.8 (singlet, 3 H), 6.9 (doublet, 2 H), and 7.2 (doublet, 2 H) ppm. (a) Propose a structure for A, including stereochemistry. (b) Explain why B is the major product in this reaction.
- Draw the structure of the ether that has a chemical formula C8H10O2, has a molecular ion peak at 138, and is represented by the IR, 'H NMR, and 13 C NMR belowUse the observed 1H NMR data to decide whether C and its dianion are aromatic, antiaromatic, or not aromatic. C shows NMR signals at –4.25 (6 H) and 8.14–8.67 (10 H) ppm. The dianion of C shows NMR signals at –3 (10 H) and 21 (6 H) ppm. Why are the signals shifted upfield (or downfield) to such a large extent?Use the observed 1H NMR data to decide whether C and its dianion are aromatic, antiaromatic, or not aromatic. C shows NMR signals at –4.25 (6 H) and 8.14–8.67 (10 H) ppm. The dianion of C shows NMR signals at –3 (10 H) and 21 (6 H) ppm. Why are the signals shifted upeld (or downeld) to such a large extent?
