Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
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Chapter 12.SE, Problem 47AP
Nitriles, R–=C≡N, undergo a hydrolysis reaction when heated with aqueous acid. What is the structure of the compound produced by hydrolysis of propanenitrile, CH3CH2C≡N, if it has IR absorptions from 2500–3100 cm-1 and at 1710 cm-1, and has M+=74?
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There are several isomeric alkanes of molecular formula C6H14.Two of these exhibit the following 1H-NMR spectra. Propose a structure for each of the isomers.
Isomer A: δ = 0.84 (d, 12 H), 1.39 (septet, 2H) ppm
Isomer B: δ = 0.84 (t, 3 H), 0.86 (s, 9H), 1.22 (q, 2H) ppm
Treatment of 2-methylpropanenitrile [(CH3)2CHCN] with CH3CH2CH2MgBr, followed by aqueous acid, affords compound V, which has molecular formula C7H14O. V has a strong absorption in its IR spectrum at 1713 cm−1, and gives the following 1H NMR data: 0.91 (triplet, 3 H), 1.09 (doublet, 6 H), 1.6 (multiplet, 2 H), 2.43 (triplet, 2 H), and 2.60 (septet, 1 H) ppm. What is the structure of V? We will learn about this reaction in Chapter 20.
There are several isomeric alkanes of molecular formula C6H14. Two of these exhibit the following 1H-NMR spectra. Propose a structure for each of the isomers.
Isomer A: δ = 0.84 (d, 12 H), 1.39 (septet, 2H) ppm
Isomer B: δ = 0.84 (t, 3 H), 0.86 (t, 9H), 1.22 (q, 2H) ppm
Chapter 12 Solutions
Organic Chemistry
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