Organic Chemistry (8th Edition)
8th Edition
ISBN: 9780134042282
Author: Paula Yurkanis 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.
As we will learn in Chapter 20, reaction of (CH3)2CO with LiC ≡ CH followed by H2O affords compound D, which has a molecular ion in its mass spectrum at 84 and prominent absorptions in its IR spectrum at 3600–3200, 3303, 2938, and 2120 cm. D shows the following 1H NMR spectral data: 1.53 (singlet, 6 H), 2.37 (singlet, 1 H), and 2.43 (singlet, 1 H) ppm. What is the structure of D?
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
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Chapter 14 Solutions
Organic Chemistry (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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- Bb.68.arrow_forwardAs we will learn in Chapter 17, reaction of (CH3)2CO with LIC≡CH followed by H2O affords compound D, which has a molecular ion in its mass spectrum at 84 and prominent absorptions in its IR spectrum at 3600−3200, 3303, 2938, and 2120 cm−1. D shows the following 1H NMR spectral data: 1.53 (singlet, 6 H), 2.37 (singlet, 1 H), and 2.43 (singlet, 1 H) ppm. What is the structure of D?arrow_forward2arrow_forward
- Q4. 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_forwardThe following is a proton NMR spectrum of a an alkyl halide with the formula C3H6Br What is the name of the compound?arrow_forward2. 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_forward
- 6) 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_forward5arrow_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_forward
- What 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_forwardThe 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_forward
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NMR Spectroscopy; Author: Professor Dave Explains;https://www.youtube.com/watch?v=SBir5wUS3Bo;License: Standard YouTube License, CC-BY