EBK ORGANIC CHEMISTRY
8th Edition
ISBN: 8220102744127
Author: Bruice
Publisher: PEARSON
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Chapter 14, Problem 50P
Determine the ratios of the chemically nonequivalent protons in a compound if the steps of the integration curves measure 40.5, 27, 13, and 118 mm, from left to right across the spectrum. Draw the structure of a compound whose 1H NMR spectrum would show these integrals in the observed order.
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A sample of dichloromethane has been contaminated with some 2,2-dichloropropane. The NMR spectrum of this sample shows two signals, one at 5.2 ppm and one at 1.9 ppm, corresponding to these two compounds respectively. The integrals of the two signals equate to 1:9 respectively. What is the mole percent of each compound in the mixture, or phrasing it another way, what percentage of the mixture is dichloromethane and what percentage is 2,2-dichloropropane?
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
The 1H NMR spectra of two carboxylic acids with molecular formula C3H5O2Cl are shown below. Identify the carboxylic acids. (The “offset” notation means that the farthest-left signal has been moved to the right by the indicated amount to fit on the spectrum; thus, the signal at 9.8 ppm offset by 2.4 ppm has an actual chemical shift of 9.8 + 2.4 = 12.2 ppm.)
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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- 11-Explain why 2-chloropropene shows signals for three kinds of protons in its 1H NMRspectrum? Draw the structure and predict the approximate values for 1H-NMR spectra.arrow_forward1. How many proton signals would you expect to see in the ¹H-NMR spectrum of the following molecule? For each of the proton signals, predict the splitting pattern, assuming that you can see only 3-bond splitting.arrow_forwardCan you please explain the 1H NMR spectra pattern of sulfamic acid?arrow_forward
- 9. (a) A compound with chemical formula C₂H₂CIBr shows the proton NMR spectrum consisting of two doublets with J-7.3 Hz. What is the molecular structure of this compound? (b) The proton chemical shifts of the two doublets from the previous question differ by 0.3 ppm. Can you consider the proton spectrum as the first order one?arrow_forwardThe 1H-NMR spectrum of 1,3-propanediol (HO-CH2-CH2-CH2-OH) shows a quintet at 1.81 ppm, a singlet at 2.75 pm, and a triplet at 3.83 ppm. Assign each signal to the protons it corresponds to in the molecule. Explain the splitting pattern observed for each signal.arrow_forwardBoth 1,4-dimethylbenzene and 1,3,5-trimethylbenzene produce a 1H NMR spectrum that has two signals. In which spectrum do the signal integrations have a 1∶3 ratio?arrow_forward
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- The 1H NMR spectrum for 4-methoxyphenyl acetate was run. Determine the integration and assign peaks for the following protons explaining why they show up at the following chemical shifts.arrow_forwardHow many peaks would the 1H NMR spectrum of the following molecule have?arrow_forwardBelow are the ¹H NMR spectrum of triphenylmethanol, benzophenone, and bromobenzene. Identify the compound corresponding to each ¹H NMR spectrum and draw the structure next to the ¹H NMR spectrum. Assign ALL peaks in each of the three ¹H NMR spectra. Hint: Conjugated systems (benzophenone) including an electronegative atom will cause a more downfield shift of ring protons in ¹H NMR compared with non-conjugated systems (bromobenzene). 8 8 8 7 7 7 6 6 6 5 5 5 4 PPM 4 PPM 4 PPM 3 3 3 2 2 2 1 1 1 0 0 0arrow_forward
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