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What is the structure of the compound with the formula C10H14 and it shows 1H-NMR spectrum: 1.2 ppm (9H singlet) 7.10 ppm (5H multiplet

Organic Chemistry

9th Edition

ISBN:9781305080485

Author:John E. McMurry

Publisher:John E. McMurry

Chapter20: Carboxylic Acids And Nitriles

Section20.SE: Something Extra

Problem 68AP: The 1H and 13C NMR spectra below belong to a compound with formula C6H10O2. Propose a structure for...

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Concept explainers

Analyzing and Predicting Spectroscopic Data

The interaction of electromagnetic radiation with the structure of molecules in the sample and their study is referred spectroscopy. Several spectroscopic methods are used to acquire sample information, and these methods are proved to be accurate, fast, and non-destructive. The information obtained about the content and composition of molecules from these spectroscopic methods is called spectroscopic data.

Question

What is the structure of the compound with the formula C₁₀H₁₄ and it shows ¹H-NMR spectrum:

1.2 ppm (9H singlet)

7.10 ppm (5H multiplet)

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Propose a structural formula for each compound consistent with its 1H-NMR and 13C-NMR spectra. (a) C5H10O2 (b) C7H14O2 (c) C6 H12O2 (d) C7H12O4 (e) C4H7ClO2 (f) C4H6O2
Following are 1H-NMR spectra for compounds G, H, and I, each with the molecular formula C5H12O. Each is a liquid at room temperature, is slightly soluble in water, and reacts with sodium metal with the evolution of a gas. (a) Propose structural formulas of compounds G, H, and I. (b) Explain why there are four lines between 0.86 and 0.90 for compound G. (c) Explain why the 2H multiplets at 1.5 and 3.5 for compound H are so complex.
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The 1H and 13C NMR spectra below belong to a compound with formula C6H10O2. Propose a structure for this compound.
What is the structure of the compound with the formula C4H10O, if it shows 1H-NMR spectrum: 1.20 ppm (6H doublet) 3.30 ppm (3H singlet) 3.55 (1H septet)
What is the structure of the compound with the formula C4H7ClO, it has a strong IR signal near 1730 cm-1, the 1H-NMR spectrum is: 1.35 ppm (3H triplet) 4.10 ppm (2H singlet) 4.25 ppm (2H quartet)
An unknown compound has a molecular formula of C5H7N. Its IR spectrum shows a signal at 3070, 2250, and 1690 cm-1. It’s 1H NMR and 13C NMR spectra are shown below. Draw the structure of this unknown compound.
When treated with an equivalent of methanol, compound A, with molecular formula C4H6Cl2O, forms the compound whose 1H NMR spectrum is shownhere. Identify compound A.
When compound A (C5H12O) is treated with HBr, it forms compound B (C5H11Br). The 1 H NMR spectrum of compound A has a 1H singlet, a 3H doublet, a 6H doublet, and two 1H multiplets. The 1 H NMR spectrum of compound B has a 6H singlet, a 3H triplet, and a 2H quartet. Identify compounds A and B.
When compound A (C5H12O) is treated with HBr, it forms compound B (C5H11Br). The 1H NMR spectrum of compound A has a 1H singlet, a 3H doublet, a 6H doublet, and two 1H multiplets. The 1H NMR spectrum of compound B has a 6H singlet, a 3H triplet, and a 2H quartet. Identify compounds A and B.
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What is the structure of the compound if its formula is C5H10O, it exhibits 13C-NMR signals Broadband decoupled: 207, 45, 28, and 12 ppm DEPT-90: no signals DEPT-135: positive signals at 28 and 12 ppm; negative signals at 45 and 16 ppm.