Identify A and B, isomers of molecular formula C3H4Cl2, from the given 1H NMR data: Compound A exhibits signals at 1.75 (doublet, 3 H, J = 6.9 Hz) and 5.89 (quartet, 1 H, J = 6.9 Hz) ppm. Compound B exhibits signals at 4.16 (singlet, 2 H), 5.42 (doublet, 1 H, J = 1.9 Hz), and 5.59 (doublet, 1 H, J = 1.9 Hz) ppm.

Identify A and B, isomers of molecular formula C3H4Cl2, from the given 1H NMR data: Compound A exhibits signals at 1.75 (doublet, 3 H, J = 6.9 Hz) and 5.89 (quartet, 1 H, J = 6.9 Hz) ppm. Compound B exhibits signals at 4.16 (singlet, 2 H), 5.42 (doublet, 1 H, J = 1.9 Hz), and 5.59 (doublet, 1 H, J = 1.9 Hz) ppm.

Organic Chemistry

9th Edition

ISBN:9781305080485

Author:John E. McMurry

Publisher:John E. McMurry

Chapter13: Structure Determination: Nuclear Magnetic Resonance Spectroscopy

Section13.SE: Something Extra

Problem 64GP: Compound F, a hydrocarbon with M+=96 in its mass spectrum, undergoes reaction with HBr to yield...

See similar textbooks

Similar questions

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.
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
Ascaridole is a natural product that has been used to treat intestinal worms. Explain why the two methyls on the isopropyl group in ascaridole appear in its 1H-NMR spectrum as four lines of equal intensity, with two sets of two each separated by 7 Hz.
Propose structures that are consistent with the following spectra. (Integral ratios are given from left to right across the spectrum.) a. The 1H NMR spectrum of a compound with molecular formula C4H10O2 has two singlets with integral ratios of 2 : 3. b. The 1H NMR spectrum of a compound with molecular formula C6H10O2 has two singlets with integral ratios of 2 : 3. c. The 1H NMR spectrum of a compound with molecular formula C8H6O2 has two singlets with integral ratios of 1 : 2.
Compound 1 has molecular formula C7H15Cl. It shows two signals in the 1H-NMR spectrum, one at 1.08 ppm and one at 1.59 ppm. The relative integrals of these two signals are 3 and 2, respectively. Propose structures for compound 1, explaining how you reach your conclusion.
The following is the predicted 1H-NMR spectrum for an unknown compound with molecular formula C6H14O . This compound is a liquid at room temperature, is slightly soluble in water, and reacts with sodium metal with the evolution of a gas.
3b. Assign the correct signal in the 1H NMR spectrum for each proton signal in the following compound. Label the signal as Ha, Hb, Hc and Hd and name all the splitting patterns.
Compound X (molecular formula C10H12O) was treated with NH2NH2, −OH to yield compound Y (molecular formula C10H14). Based on the 1HNMR spectra of X and Y given below, what are the structures of X and Y?
Figure 1 shows the following spectrum of a compound with formula C5H10O, with interesting coupling patterns at 2.4 and 9.8 ppm. Expansions of these two peaks are shown in Figure 2. Expansions of the other patterns (not shown) are given as follows: 0.92 ppm(triplet), 1.45 ppm (sextet), and 1.61 ppm (quintet).1.Draw the structure of the compound.2.Assign the proton signals in the 1H NMR spectrum according to the answer in3(a). 3.Draw tree diagrams of the peaks at 2.4 and 9.8 ppm.4.Assign the coupling constants of the peaks at 2.4 and 9.8 ppm in tree diagram3(c).
Compound A, with molecular formula C4H9Cl, shows two signals in its 13C NMR spectrum. Compound B, an isomer of compound A, shows foursignals, and in the proton-coupled mode, the signal farthest downfield is a doublet. Identify compounds A and B.
Compound A, with molecular formula C4H9Cl, shows two signals in its 13C NMR spectrum. Compound B, an isomer of compound A, shows four signals, and in the proton-coupled mode, the signal farthest downfield is a doublet. Identify compounds A and B
Describe the 1H NMR spectrum of each compound. State how many NMR signals are present, the splitting pattern for each signal, and the approximate chemical shift