EBK ORGANIC CHEMISTRY
8th Edition
ISBN: 8220102744127
Author: Bruice
Publisher: PEARSON
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Chapter 14, Problem 61P
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An alkyl halide reacts with an alkoxide ion to form a compound whose 1H NMR spectrum is shown here. Identify the alkyl halide and the alkoxide ion.
Show the proton and carbon NMR peaks. This can be the NMR graph OR a list of peaks labeled 1,2,3 or a, b, c. Label
the 1H NMR spectral data (1,2,3 or a, b, c) and match the peaks to ALL the product molecule's H by labeling them
(1,2,3 or a, b, c). Show that you know which 1H-NMR peaks correspond to each hydrogen atoms on your molecule.
Label the 13C NMR spectral data (1,2,3 or a, b, c) and match the peaks to ALL the product molecule's C by labeling
them (1,2,3 or a, b, c). Show that you know which 13C NMR peaks correspond to each hydrogen atoms on your
molecule.
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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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- 2arrow_forwardThe following is a proton NMR spectrum of a an alkyl halide with the formula C3H6Br What is the name of the compound?arrow_forward6) The NMR spectrum of this dimethyl ether is complicated, but the diphenol has a very simple NMR: there are only two types of protons on the rings (marked a and b). Explain. OMe 0 a b OH a OMe dimethyl ether Он diphenol barrow_forward
- 5arrow_forwardA compound is a ketone of molecular formula C7H14O. Its 13C NMR spectrum is shown in Figure. What is the structure of the compound?arrow_forwardWhat is the structure(s) of each peak and what compound(s) does the NMR show. Reactants to form this NMR by diels-alder reaction are Anthracene, Maleic anhydride, and xylenearrow_forward
- The two isomeric compounds with the formula C3H5ClO2 have NMR spectra shown in 4a and 4b below. The downfield protons appearing in the NMR spectra at about 12.1 and 11.5 ppm, respectively, are shown as insets. Determine the structure of the two isomersarrow_forward13. Compound A has molecular formula C8H18. It shows one singlet in the 1H-NMR spectrum. Identify A and explain your reasoning.arrow_forwardUsing proton NMR spectra, how could a chemist distinguish between the following two compounds? H. H. СОСН Ph COCH; Ph H. Compound A Compound B The alkene protons in compound A display a larger coupling constant. Compound A and compound B show a different number of signals in the proton spectrum. The alpha alkene proton would be more shifted than the beta alkene proton in compound B Proton NMR spectroscopy cannot be used to distinguish between these compounds. The alkene protons in compound B display a larger coupling constant.arrow_forward
- 2 The IR and 1H-NMR spectra of a compound with molecular formula C4H7ClO2 are shown below. Your objective as a group is to propose a structure for this compound, explaining how you reach your decision. Using all the information you have been given, in a post with others in your group share your initial ideas about the possible structure of the compound. Then use comments to interact with the other students in the group and propose a final answer to the problem. In the comment phase, you should comment on the postings of at least two other students.arrow_forward5. A compound having molecular formula C,H,OS reacts with hydrazine hydrate forming a product C with molecular formula C₁H,N₂S₂. The ¹H-NMR and ¹C-NMR spectra of the product is given below. Identify compounds A and C. Also, assign each NMR peak. Answer as soon as possible within 10 minutes with proper explanation in handwritten form. Don't answer after 11:58 PM Otherwise I will downvote and report !! Thank youarrow_forward(II) Study this aromatic molecule and answer the following questions: Br H3 NO2 Br a) How many 'H-NMR signals this compound will show? B What will be the splitting (coupling) of H1, H2, and H3? H1 H2 H3 c) Which of the two hydrogens, Hl or H3 will show larger coupling, and which will show smaller coupling? Explain your answer: d) Draw the signal for H2:arrow_forward
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