Essential Organic Chemistry, Global Edition
3rd Edition
ISBN: 9781292089034
Author: Paula Yurkanis Bruice
Publisher: PEARSON
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Chapter 10.27, Problem 42P
The 1H NMR spectra of two
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The 1H NMR spectra of two carboxylic acids with molecular formula C3H5O2Cl are shown below. Identify the carboxylic acids. (The “offset” notation means that the farthest-left signal has been moved to the right by the indicated amount to fit on the spectrum; thus, the signal at 9.8 ppm offset by 2.4 ppm has an actual chemical shift of 9.8 + 2.4 = 12.2 ppm.)
The 1H NMR spectra of two carboxylic acids with molecular formula C3H5O2Cl are shown below. Identify the carboxylic acids. (The “offset” notation means that the farthest-left signal has been moved to the rightby the indicated amount to fit on the spectrum; thus, the signal at 9.8 ppm offset by 2.4 ppm has an actual chemical shift of 9.8 + 2.4 = 12.2 ppm.)
The 1H NMR spectrum of CH3OH recorded on a 500 MHz NMR spectrometer consists of two signals, one due to the CH3 protons at 1715 Hz and one due to the OH proton at 1830 Hz, both measured downfield from TMS. (a) Calculate the chemical shift of each absorption. (b) Do the CH3 protons absorb upfield or downfield from the OH proton?
Chapter 10 Solutions
Essential Organic Chemistry, Global Edition
Ch. 10.1 - Prob. 1PCh. 10.2 - What would distinguish the mass spectrum of...Ch. 10.2 - Prob. 3PCh. 10.3 - Prob. 5PCh. 10.3 - Suggest possible molecular formulas for a compound...Ch. 10.3 - Prob. 7PCh. 10.4 - Prob. 8PCh. 10.4 - Prob. 9PCh. 10.5 - Prob. 10PCh. 10.5 - Prob. 11P
Ch. 10.6 - Identify the ketone responsible for the mass...Ch. 10.6 - Prob. 13PCh. 10.8 - Prob. 14PCh. 10.8 - Prob. 15PCh. 10.12 - Which will occur at a larger wavenumber: a. a C :...Ch. 10.13 - Which will occur at a larger wavenumber: a. the C...Ch. 10.13 - Prob. 18PCh. 10.13 - Prob. 19PCh. 10.13 - Which will show an O 8 H stretch at a larger...Ch. 10.14 - Prob. 21PCh. 10.14 - Prob. 22PCh. 10.15 - Prob. 23PCh. 10.15 - Prob. 24PCh. 10.17 - Prob. 25PCh. 10.18 - Prob. 26PCh. 10.18 - Prob. 27PCh. 10.19 - Prob. 28PCh. 10.19 - Prob. 29PCh. 10.22 - How many signals would you expect to see in the 1H...Ch. 10.22 - Prob. 31PCh. 10.22 - Prob. 32PCh. 10.23 - Where would you expect to find the 1H NMR signal...Ch. 10.24 - Prob. 34PCh. 10.25 - Prob. 35PCh. 10.25 - Prob. 36PCh. 10.25 - Prob. 37PCh. 10.26 - Prob. 38PCh. 10.26 - Which of the following compounds is responsible...Ch. 10.27 - Prob. 40PCh. 10.27 - Prob. 41PCh. 10.27 - The 1H NMR spectra of two carboxylic acids with...Ch. 10.28 - Prob. 43PCh. 10.28 - Prob. 44PCh. 10.28 - Prob. 45PCh. 10.28 - Describe the 1H NMR spectrum you would expect for...Ch. 10.28 - Identify the compound with molecular formula...Ch. 10.29 - Prob. 48PCh. 10.29 - Prob. 49PCh. 10.29 - Identify the compound with a molecular formula of...Ch. 10 - In the mass spectrum of the following compounds,...Ch. 10 - For each of the following pairs of compounds,...Ch. 10 - Draw the structure of a saturated hydrocarbon that...Ch. 10 - Prob. 54PCh. 10 - Prob. 55PCh. 10 - How could you use UV spectroscopy to distinguish...Ch. 10 - Prob. 57PCh. 10 - Predict the relative intensities of the molecular...Ch. 10 - Prob. 59PCh. 10 - List the following compounds in order from highest...Ch. 10 - How can 1H NMR be used to prove that the addition...Ch. 10 - There are four esters with molecular formula...Ch. 10 - Prob. 63PCh. 10 - Prob. 64PCh. 10 - Each of the IR spectra presented here is...Ch. 10 - Prob. 66PCh. 10 - Five compounds are shown for each of the following...Ch. 10 - Prob. 68PCh. 10 - Prob. 69PCh. 10 - Phenolphthalein is an acidbase indicator. In...Ch. 10 - Which one of the following five compounds produced...Ch. 10 - Prob. 72PCh. 10 - Prob. 73PCh. 10 - Prob. 74PCh. 10 - How could 1H NMR distinguish between the compounds...Ch. 10 - Prob. 76PCh. 10 - Prob. 77PCh. 10 - The 1H NMR spectra of three isomers with molecular...Ch. 10 - The 1H NMR spectra of three isomers with molecular...Ch. 10 - Identify the following compounds. (Relative...Ch. 10 - An alkyl halide reacts with an alkoxide ion to...Ch. 10 - Determine the structure of a compound with...
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- The 1H NMR spectrum of 1,2-dimethoxyethane (CH3OCH2CH2OCH3) recorded on a 300 MHz NMR spectrometer consists of signals at 1017 Hz and 1065 Hz downfield from TMS.(a) Calculate the chemical shift of each absorption. (b) At what frequency would each absorption occur if the spectrum were recorded on a 500 MHz NMR spectrometer?arrow_forwardThe 1H NMR spectrum of CH3OH recorded on a 500 MHz NMR spectrometer consists of two signals, one due to the CH3 protons at 1715 Hz and one due to the OH proton at 1830 Hz, both measured downeld from TMS. (a) Calculate the chemical shift of each absorption. (b) Do the CH3 protons absorb upeld or downeld from the OH proton?arrow_forwardThe following molecule will give two signals in the proton (¹H) NMR. H₂C What is the ratio of the signal intensities for the two peaks? 2:2 O 3:1 3:2 CH₂ O 2:1arrow_forward
- Assign all of the signals in the ¹H NMR spectrum for propyl acetate. Fill in the table below with the 'H NMR data. Number each proton (or set of protons) to match the corresponding peak in the NMR. Integration Splitting Propyl acetate structure with protons labeled Signal - Chemical shift (ppm) 1 2 3 4 11 propyl acetate 10 9 8 7 6 5 ppm 2H, triplet 4 3 3H, singlet 3H, triplet 2H, sextet 2 1 Figure 3.7 ¹H NMR spectrum for propyl acetate. 0arrow_forwardCompound 1 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. Compound 2 has molecular formula C7H15Br. It shows two signals in the 1H-NMR spectrum, one at 1.08 ppm and one at 1.59 ppm. The relative integrals of these two signals are 3 and 2, respectively. Propose structures for compounds 1 and 2, explaining how you reach your conclusion.arrow_forwardPlease complete the given question and explainarrow_forward
- 5. Dibromomethane contains 2 equivalent protons, so just one signal on the H NMR spectrum for dibramomethane is expected to be seen. determine the expected chemical shift for the dibromomethane signal.arrow_forwardDescribe the 1H-NMR spectrum of 4-bromoaniline (chemical shift, integration, multiple). Make a table and describe the results.arrow_forwardThe line of integration of the two signals in the 1H-NMR spectrum of a ketone with the molecular formula C7H14O rises 62 and 10 chart divisions, respectively. Calculate the number of hydrogens giving rise to each signal and propose a structural formula for this ketone.arrow_forward
- Assign the C (Roman numerals) and H (Roman letters) atoms in the given structures using the 13C (top) and 1H (bottom) NMR spectra providedarrow_forwardWith a 90 MHz NMR instrument, the three proton signals for 2,2-dimethyl-1-propanol are observed at 80, 162, and 293 Hz, respectively, from the reference tetramethylsilane (TMS). Calculate the chemical shift (δ) values for these three signalsarrow_forward(a) What would be the chemical shift of a peak that is observed at 655.2 Hz from the reference tetramethylsilane (TMS) recorded using a 90 MHz spectrometer ? (b) At what frequency would the chemical shift of chloroform (CHCl3, δ = 7.28 ppm) occur relative to TMS on a spectrum recorded on a 300 MHz spectrometer? (c) At what frequency and chemical shift would the signal for chloroform occur when using a 1 GHz NMR spectrometer?arrow_forward
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