Organic Chemistry, Books a la Carte Edition (8th Edition)
8th Edition
ISBN: 9780134074580
Author: Bruice, Paula Yurkanis
Publisher: PEARSON
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Textbook Question
Chapter 14, Problem 59P
There are four esters with molecular formula C4H8O2. How can they be distinguished by 1H NMR?
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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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- Compound P has molecular formula C5H9ClO2. Deduce the structure of P from its 1H and 13C NMR spectra.arrow_forward16-17 Propylamine (bp 48°C), ethylmethylamine (bp 37°C), and trimethylamine (bp 3°C) are constitutional isomers with the molecular formula C3HgN. Account for the fact that trimethylamine has the lowest boiling point of the three and propylamine has the highest.arrow_forwardCompound H (C8H6O3) gives a precipitate when treated with hydroxylamine in aqueous ethanol and a silver mirror when treated with Tollens solution. Following is its 1H-NMR spectrum. Deduce the structure of compound H.arrow_forward
- Compound 2 has molecular formula C6H12. It shows three signals in the 1H-NMR spectrum, one at 0.96 ppm, one at 2.03 ppm, and one at 5.33 ppm. The relative integrals of these three signals are 3, 2, and 1, respectively. Provide structure for compound 2, explain how you reached your conclusion.arrow_forwardCompound A has molecular formula C7H7X. Its 1H-NMR spectrum shows a singlet at 2.26 ppm and two doublets, one at 6.95 ppm and one at 7.28 ppm. The singlet has an integral of three and the doublets each have an integral of two. Its 13C-NMR shows five signals. The mass spectrum of A shows a peak at m/z = 170 and another peak at m/z = 172; the relative height of the two peaks is 1:1 respectively. - Identify what atom X is, explaining your reasoning - Identify Compound A, explaining your reasoning Compound A is treated with a mixture of nitric and sulfuric acids to generate Compound B. The 1H-NMR spectrum of B shows two singlets, one at 2.52 pm and one at 8.13 ppm. The 13C-NMR spectrum of B shows five signals. The mass spectrum of B shows a peak at m/z = 260 and another peak at m/z = 262; the relative height of the two peaks is 1:1 respectively. - Identify compound B, explaining your reasoning Compound B is treated with sodium ethoxide to generate compound C. The 1H-NMR spectrum of C shows…arrow_forwardHow can 1H NMR distinguish between the compounds in the following pairs?arrow_forward
- Compound X (molecular formula C10H12O) was treated with NH2NH2,−OH to yield compound Y (molecular formula C10H14). Based on the 1H NMR spectra of X and Y given below, what are the structures of X and Y?arrow_forwardThe two isomeric carboxylic acids that give the following NMR spectra both have the formula C3H5C1O2. Draw their structures.arrow_forwardExplain how the following compounds, each with the same molecular formula, could be distinguished by their 1H NMR spectra.arrow_forward
- Compound A has molecular formula C7H7X. Its ¹H-NMR spectrum shows a singlet at 2.26 ppm and two doublets, one at 6.95 ppm and one at 7.28 ppm. The singlet has an integral of three and the doublets each have an integral of two. Its 13C- NMR shows five signals. The mass spectrum of A shows a peak at m/z 170 and another peak at m/z = 172; the relative height of the two peaks is 1:1 respectively. - Identify what atom X is, explaining your reasoning - Identify Compound A, explaining your reasoning Compound A is treated with a mixture of nitric and sulfuric acids to generate Compound B. The ¹H-NMR spectrum of B shows two singlets, one at 2.52 pm and one at 8.13 ppm. The 13C-NMR spectrum of B shows five signals. The mass spectrum of B shows a peak at m/z = 260 and another peak at m/z = 262; the relative height of the two peaks is 1:1 respectively. - Identify compound B, explaining your reasoning Compound B is treated with sodium ethoxide to generate compound C. The ¹H-NMR spectrum of C shows…arrow_forwardIdentify the compound with molecular formula C8H10O that gives the IR and 1H NMR spectra shown here.arrow_forwardThe following NMR spectra were obtained from a compound with the molecular formula C4H6O. Use this information to predict its structure.arrow_forward
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