Organic Chemistry, Books a la Carte Edition (8th Edition)
8th Edition
ISBN: 9780134074580
Author: Bruice, Paula Yurkanis
Publisher: PEARSON
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Chapter 14 Solutions
Organic Chemistry, Books a la Carte Edition (8th Edition)
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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- Tabulate your 1H NMR data of 2-(2-nitrophenyl)acetonitrile. Label each proton on the structure, and list them separately in a table that is similar to the example below. Be sure to include a row for each unique proton. The H NMR spectra for the structure is attached also.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_forwardQ4. The following is the 13C NMR spectrum of a highly concentrated solution of dicyclopentadiene obtained in chloroform-d. Despite the high purity of the compound based on ¹H NMR, there is a massive peak observed at 77.2 ppm in this 13C spectrum, which doesn't correspond to any resonances expected for dicyclopentadiene. What is this peak, and why do you not see a corresponding peak for this compound in your ¹H NMR spectrum? 79-751 <-136.22 -132.62 132.27 132.23 135 130 125 120 115 110 105 100 95 90 85 80 75 70 65 60 55 50 45 40 35 30arrow_forward
- 2. The following synthesis was planned. The 'H NMR spectrum of the final product was run and is presented below. Was the synthesis successful? If not, what is the actual product and why? sos H2N' 10 로 1H 2H 2H 8 1. NaNO2 HCI (aq.) 2H 2H 6 2. H 1H 1H PPM 1H OH 1H HO 2arrow_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_forward6. Given the ¹H NMR provided, what is the molecule? The molecular formula is C7H₁40. There is a strong peak in the IR spectrum at 1700 cm³¹. Note that the integration line is shown below on the spectrum to show you the ratios of protons in the molecule. Identify which peak corresponds to which protons on the molecule you drew. You can circle the protons on your molecule and use "2H," "3H," or "9H" to identify which peak belongs to which protons on your molecule. 6 5 4 Chemical shift (8) 3 2H 3H 2 r 9H 1 0 (ppm)arrow_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
- An unknown compound has the molecular formula C7H14O, and its 1H NMR and 13C NMR spectra are shown here. Determine the structure of the unknown compound and draw it below. Note that there are no peaks above 3 ppm in the 1H NMR, and the numbers present on the 1H NMR are the integration values for each set of peaks. (Also note that the protons responsible for causing the splitting pattern seen for the "9 peak" multiplet have similar coupling constants.)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_forwardYou are given an unknown compound B with the molecular formula C5H12O and you take an 1H NMR of B (See below). You were told that B formed when A was reacted with a catalytic amount of H2SO4 and an excess of H2O, A formed. An IR spectra of A is below. Identify A and B in the spaces belowarrow_forward
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