EBK ORGANIC CHEMISTRY
8th Edition
ISBN: 8220102744127
Author: Bruice
Publisher: PEARSON
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Chapter 14, Problem 67P
The 1H NMR spectra of two compounds, each with molecular formula C11H16, are shown here. Identify the compounds.
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1Compound 1 has molecular formula C7H16. It shows three signals in the 1H-NMR spectrum, one at 0.85 ppm, one at 1.02 ppm, and one at 1.62 ppm. The relative integrals of these three signals are 6, 1, and 1, respectively.
Compound 2 has molecular formula C7H14. It shows three signals in the 1H-NMR spectrum, one at 0.98 ppm, one at 1.36 ppm, and one at 1.55 ppm. The relative integrals of these three signals are 3, 2, and 2, respectively.
Propose structures for compounds 1 and 2, explaining how you reach your conclusion.
Compound 1 has molecular formula C6H12. It shows three signals in the 1H-NMR spectrum, one at 0.96 ppm, one at 2.03 ppm, and one at 5.33 ppm. The relative integrals of these three signals are 3, 2, and 1, respectively.
Compound 2 has molecular formula C7H15Br. 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 compounds 1 and 2, explaining how you reach your conclusion.
The 1H NMR spectra of three isomers with molecular formula C7H14O are shown here. Which isomer produces which spectrum?
Chapter 14 Solutions
EBK ORGANIC CHEMISTRY
Ch. 14.1 - Prob. 1PCh. 14.1 - Prob. 2PCh. 14.4 - How many signals would you expect to see in the 1H...Ch. 14.4 - How many signals would you expect to see in the 1H...Ch. 14.4 - How could you distinguish the 1H NMR spectra of...Ch. 14.4 - Draw an isomer of dichlorocyclopropane that gives...Ch. 14.5 - Prob. 7PCh. 14.5 - Prob. 8PCh. 14.5 - Prob. 9PCh. 14.5 - Where would you expect to find the 1H NMR signal...
Ch. 14.6 - Prob. 11PCh. 14.7 - Prob. 12PCh. 14.7 - Prob. 13PCh. 14.7 - Without referring to Table 14.1, label the proton...Ch. 14.8 - [18]-Annulene shows two signals in its 1H NMR...Ch. 14.9 - How would integration distinguish the 1H NMR...Ch. 14.9 - Which of the following compounds is responsible...Ch. 14.10 - Prob. 19PCh. 14.10 - Explain how the following compounds, each with the...Ch. 14.10 - The 1H NMR spectra of two carboxylic acids with...Ch. 14.11 - Draw a diagram like the one shown in Figure 14.12...Ch. 14.12 - Indicate the number of signals and the...Ch. 14.12 - Explain the relative chemical shifts of the...Ch. 14.12 - How can their 1H NMR spectra distinguish the...Ch. 14.12 - Identify each compound from its molecular formula...Ch. 14.12 - Predict the splitting patterns for the signals...Ch. 14.12 - Describe the 1H NMR spectrum you would expect for...Ch. 14.12 - Propose structures that are consistent with the...Ch. 14.13 - Prob. 30PCh. 14.13 - Identify the compound with molecular formula...Ch. 14.14 - Prob. 32PCh. 14.15 - a. For the following compounds, which pairs of...Ch. 14.15 - How would the 1H NMR spectra for the four...Ch. 14.17 - Explain why the chemical shift of the OH proton of...Ch. 14.17 - Prob. 38PCh. 14.17 - Prob. 39PCh. 14.17 - Prob. 40PCh. 14.20 - Answer the following questions for each compound:...Ch. 14.20 - Prob. 42PCh. 14.20 - How can 1,2-, 1,3-, and 1,4-dinitrobenzene be...Ch. 14.20 - Identify each compound below from its molecular...Ch. 14.22 - Prob. 45PCh. 14.22 - What does cross peak X in Figure 14.34 tell you?Ch. 14 - Prob. 47PCh. 14 - Draw a spitting diagram for the Hb proton and give...Ch. 14 - Label each set of chemically equivalent protons,...Ch. 14 - Determine the ratios of the chemically...Ch. 14 - How can 1H NMR distinguish between the compounds...Ch. 14 - Prob. 52PCh. 14 - Match each of the 1H NMR spectra with one of the...Ch. 14 - The 1H NMR spectra of three isomers with molecular...Ch. 14 - Prob. 55PCh. 14 - Prob. 56PCh. 14 - Compound A, with molecular formula C4H9Cl, shows...Ch. 14 - Would it be better to use 1H NMR or 13C NMR...Ch. 14 - There are four esters with molecular formula...Ch. 14 - Identify the compound with molecular formula C6H14...Ch. 14 - An alkyl halide reacts with an alkoxide ion to...Ch. 14 - The 1H NMR spectra of three isomers with molecular...Ch. 14 - Identity each of the following compounds from its...Ch. 14 - Identity each of the following compounds from its...Ch. 14 - Prob. 65PCh. 14 - How can the signals in the 6.5 to 8.1 ppm region...Ch. 14 - The 1H NMR spectra of two compounds, each with...Ch. 14 - Draw a splitting diagram for the Hb proton if Jbc...Ch. 14 - Sketch the following spectra that would be...Ch. 14 - How can 1H NMR be used to prove that the addition...Ch. 14 - Identity each of the following compounds from its...Ch. 14 - Dr. N. M. Arr was called in to help analyze the 1H...Ch. 14 - Calculate the amount of energy (in calories)...Ch. 14 - The following 1H NMR spectra are four compounds,...Ch. 14 - When compound A (C5H12O) is treated with HBr, it...Ch. 14 - Identity the compound with molecular formula...Ch. 14 - Identity each of the following compounds from its...Ch. 14 - Prob. 78PCh. 14 - Identify each of the following compounds from its...
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- There are four esters with molecular formula C4H8O2. How can they be distinguished by 1H NMR?arrow_forwardDraw the H1 NMR spectra of ethylcyclopropane. Draw the chemical structure and predict the proton splitting and chemical shifts.arrow_forwardHow can 1H NMR distinguish between the compounds in the following pairs?arrow_forward
- 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.arrow_forwardThe 1H-NMR spectrum of ethanol shows a triplet at 1.23 ppm, a singlet at 2.61 pm, and a quartet at 3.69 ppm. Assign each signal to the protons it corresponds to in the molecule. Explain the splitting pattern observed for each signal.arrow_forwardAn NMR spectrum was run for the following compound. Assign proton NMR peaks and explain.arrow_forward
- How can their 1H NMR spectra distinguish the following compounds?arrow_forwardHow many unique 13C NMR and 1H NMR signals exist in the spectrum for the compound: 1,3-dibromobenzene?arrow_forwardHow many different 13C-absorption lines and how many 'H- resonances (disregard splitting and assume that solvent exchange of acidic hydrogens does NOT take place) are observed in the spectrum of each of the following compounds? (H3C)3C-C(CH3)2 CI A H3C (H3C)3C B CH3 CH3 H₂C= -COOH C CH-CI H3C-C-CH Cl Br Darrow_forward
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