An unknown organic compound is isolated. The compound produces a molecular ion at m/z = 101. There is no significant M+2 peak. The IR spectrum shows peaks ~2950 cm1. It does not have any peaks above 3000, nor around 1600-1800 or 1050 cm '. The 'H-NMR and 13C-NMR spectra are shown below. What is the name of this compound (IUPAC and common name are both acceptable)? 2H PPM 40 30 PPM 20 10

An unknown organic compound is isolated. The compound produces a molecular ion at m/z = 101. There is no significant M+2 peak. The IR spectrum shows peaks ~2950 cm1. It does not have any peaks above 3000, nor around 1600-1800 or 1050 cm '. The 'H-NMR and 13C-NMR spectra are shown below. What is the name of this compound (IUPAC and common name are both acceptable)? 2H PPM 40 30 PPM 20 10

Organic Chemistry

8th Edition

ISBN:9781305580350

Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Chapter13: Nuclear Magnetic Resonance Spectroscopy

Section: Chapter Questions

Problem 13.17P: Following are 1H-NMR spectra for compounds G, H, and I, each with the molecular formula C5H12O. Each...

See similar textbooks

Similar questions

A 13C NMR spectrum of commercially available 2,4-pentanediol, shows five peaks at 23.3, 23.9, 46.5, 64.8, and 68.1 . Explain.
The proton NMR spectrum for a compound with formula C10H12O2 is shown below. The infrared spectrum has a strong band at 1711 cm-1. The broadband-decoupled 13C NMR spectral results are tabulated along with the DEPT135 and DEPT90 information. Draw the structure of this compound.
3-Bromo-1-phenyl-1-propene shows a complex NMR spectrum in which the vinylic proton at C2 is coupled with both the C1 vinylic proton (J = 16 Hz) and the C3 methylene protons (J = 8 Hz). Draw a tree diagram for the C2 proton signal, and account for the fact that a five-line multiplet is observed.
When measured on a spectrometer operating at 200 MHz, chloroform (CHCl3) shows a single sharp absorption at 7.3 Î´. (a) How many parts per million downfield from TMS does chloroform absorb? (b) How many hertz downfield from TMS would chloroform absorb if the measurement were carried out on a spectrometer operating at 360 MHz? (c) What would be the position of the chloroform absorption in Î´ units when measured on a 360 MHz spectrometer?
Compound F, a hydrocarbon with M+=96 in its mass spectrum, undergoes reaction with HBr to yield compound G. Propose structures for F and G, whose 13C NMR spectral data are given below. Compound F Broadband-decoupled 13C NMR: 27.6, 29.3, 32.2, 132.4 DEPT-90: 132.4 DEPT-135: positive peak at 132.4 ; negative peaks at 27.6, 29.3, 32.2 Compound G Broadband-decoupled 13C NMR: 25.1, 27.7, 39.9, 56.0 DEPT-90: 56.0 DEPT-135: positive peak at 56.0 ; negative peaks at 25.1, 27.7, 39.9
The 1H and 13C NMR spectra of compound A, C8H9Br, are shown. Propose a structure for A, and assign peaks in the spectra to your structure.
How would you use NMR (either 13C or 1H) to distinguish between the following pairs of isomers?
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.
Compound A, a hydrocarbon with M+=96 in its mass spectrum, has the 13C spectral data given below. On reaction with BH3, followed by treatment with basic H2O2. A is converted into B, whose, 13C spectral data are also given below. Propose structures for A and B. Compound A Broadband-decoupled l3C NMR: 26.8, 28.7, 35.7, 106.9, 149.7 DEPT-90: no peaks DEPT-135: no positive peaks; negative peaks at 26.8, 28.7, 35.7, 106.9 Compound B Broadband-decoupled 13C NMR: 26.1, 26.9, 29.9, 40.5, 68.2 DEPT-90: 40.5 DEPT-135: positive peak at 40.5 ; negative peaks at 26.1, 26.9. 29.9, 68.2
Propose a structure consistent with the following spectral data for a compound C8H18O2: IR: 3350 cm-1 1H NMR: 1.24 Î´ (12 H, singlet); 1.56 Î´ (4 H, singlet); 1.95 Î´ (2 H, singlet)
Carboxylic acids (RCO2H) react with alcohols (ROH) in the presence of an acid catalyst. The reaction product of propanoic acid with methanol has the following spectroscopic properties. Propose a structure. MS: M+=88 IR: 1735 cm-1 1H NMR: 1.11 (3 H, triplet, J=7 Hz); 2.32 (2 H, quartet, J=7 Hz); 3.65 (3 H, singlet) 13C NMR: 9.3, 27.6, 51.4, 174.6
3-Methyl-2-butanol has five signals in its 13C NMR spectrum at 17.90, 18.15, 20.00, 35.05, and 72.75 . Why are the two methyl groups attached to C3 nonequivalent? Making a molecular model should be helpful.