(b) Reaction between an aldehyde and ketone (see below), in base gives a compound A with 'H NMR spectrum: 8 1.10 (9H, s), 1.17 (9H, s), 6,4 (1H, d. J 15 Hz), 7.0 (1H, d. J 15 Hz). What is its structure? When this compound reacts with HBr it gives compound B with this NMR spectrum: õ 1.08 (9H, s), 1.13 (9H, s), 2.71 (1H, dd, J 1.9 Hz, 17.7 Hz), 3.25 (1H, dd, J 10.0 Hz, 17.7 Hz), 4.38 (1H, dd, J 1.9 Hz, 10.0 Hz). Suggest a structure, assign the spectrum and give a mechanism for the formation of compound B. base A HBr C1H200 CH21Bro

(b) Reaction between an aldehyde and ketone (see below), in base gives a compound A with 'H NMR spectrum: 8 1.10 (9H, s), 1.17 (9H, s), 6,4 (1H, d. J 15 Hz), 7.0 (1H, d. J 15 Hz). What is its structure? When this compound reacts with HBr it gives compound B with this NMR spectrum: õ 1.08 (9H, s), 1.13 (9H, s), 2.71 (1H, dd, J 1.9 Hz, 17.7 Hz), 3.25 (1H, dd, J 10.0 Hz, 17.7 Hz), 4.38 (1H, dd, J 1.9 Hz, 10.0 Hz). Suggest a structure, assign the spectrum and give a mechanism for the formation of compound B. base A HBr C1H200 CH21Bro

Chemistry

10th Edition

ISBN:9781305957404

Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Chapter1: Chemical Foundations

Section: Chapter Questions

Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...

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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.
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Propose a structure that is consistent with each set of 1H NMR data. IR data is provided for some compound
Reaction of butanenitrile (CH3CH2CH2CN) with methylmagnesium bromide (CH3MgBr), followed by treatment with aqueous acid, forms compound G. G has a molecular ion in its mass spectrum at m/z = 86 and a base peak at m/z = 43. G exhibits a strong absorption in its IR spectrum at 1721 cm−1 and has the 1H NMR spectrum given below. What is the structure of G?
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.
(a) The 'H-NMR spectrum of cyclobutanone shows two signals - signal A at 3.00 ppm and signal B at 1.95 ppm. Give the multiplicity of each signal. cyclobutanone (b) When cyclobutanone is treated with D20 and NaOD, the only signal observable in the 1H-NMR is a singlet at 2.00 ppm. Explain why this is the case. [Note: Deuterium atoms do not display signals in the TH-NMR spectrum]
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provide the structure for this nmr spectra
Reaction of butanenitrile (CH3CH2CH2CN) with methylmagnesium bromide (CH3MgBr), followed by treatment with aqueous acid, forms compound G. G has a molecular ion in its mass spectrum at m/z = 86 and a base peak at m/z = 43. G exhibits a strong absorption in its IR spectrum at 1721 cm−1 and has the 1H NMR spectrum given below. What is the structure of G? We will learn about the details of this reaction in Chapter 22.