EBK ORGANIC CHEMISTRY
8th Edition
ISBN: 8220102744127
Author: Bruice
Publisher: PEARSON
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Textbook Question
Chapter 14.12, Problem 24P
Explain the relative chemical shifts of the benzene ring protons in Figure 14.18.
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4.
There are two spectra on the next page, one for each of the following compounds:
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Draw a resonance structure of each compound (use the alkene electrons, and think of D as an
enol ether). How could these resonance structures be used to distinguish the spectra? (Think
about, in particular: a) How can the chemical shifts of the vinylic protons be used to distinguish
which spectrum belongs to which compound? b) How can the chemical shift of the aliphatic
(i.e. sp³) methylene group be used to distinguish which spectrum belongs to which compound?)
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4. Identify the different types of carbons and predict their approximate chemical shift. (See
Figure 13-18.)
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Explain the relative chemical shifts of the benzene ring protons.
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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- True or False: The chemical shift of a particular proton provides information about the electronic/chemical environment of that proton. Could you explain how to do this in detail?arrow_forwardChemistryarrow_forwardFor the following spectra, IF A SPECTRA can be readily matched to a molecule do so and then indicate the absorptions on the spectra. For any spectra and molecules that can’t be easily assigned explain why, and also identify absorptions on the spectra.arrow_forward
- Predict the approximate chemical shifts of the protons in the following compounds. (a) benzene (b) cyclohexanearrow_forward5. L-dopa is used in the treatment of Parkinson's disease. Identify the four most acidic protons and arrange them in order of increasing acidity. :O: g HO: :OH 6. Coumarins are a class of natural products produced by plants and animals. It has a wide variety of applications in cosmetics, food industry and fluorescent laser dyes. In the ¹HNMR spectrum of coumarin derivate shown below, the two signals farthest downfield are at 7.38 and 8.42 pm. Identify the two protons that most likely give rise to these signals and justify your answer using resonance structures. :O:arrow_forwardChoose the most possible compound for this FTIR spectrum. a. 2-pentanone b. 1-pentanol c. 2-methyl pentane d. 1-bromopentanearrow_forward
- 2. What would you predict to be the hottest in relation to spectra? A violet object, a green object, or red object and why?arrow_forwardcould you help me work out these problem step by steparrow_forward10) For each spectrum, give the following: What type of spectroscopy produces a spectrum that looks like that What type or types of energy transitions are involved (i.e. electron going from one atomic orbital to another, molecule going from a lower vibrational state to a higher vibrational state, etc.) What quantum mechanical model or theory provides a description for the type of spectroscopy (i.e. harmonic oscillator model, molecular orbital theory, etc.) What part of the electromagnetic spectrum is absorbed or emitted by the energy transitions for the type of spectroscopy Describe what information this type of spectroscopy can give us about an atom or molecule and how the spectrum is interpretedarrow_forward
- 6. Assign the chemical shifts for the compound listed below. Farrow_forwardThe 1H-NMR spectrum of 1-bromopropane shows three signals and the 1H-NMR spectrum of 2-bromopropane shows two signals. Draw these two molecules and determine the relative integrals of each signal.arrow_forwardOnce again, the question is included in the problem. I want to compare it to my answer!arrow_forward
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