Essential Organic Chemistry, Global Edition
3rd Edition
ISBN: 9781292089034
Author: Paula Yurkanis Bruice
Publisher: PEARSON
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Textbook Question
Chapter 10, Problem 80P
Identify the following compounds. (Relative integrals are given from left to right across the spectrum.)
- a. The 1H NMR spectrum of a compound with molecular formula C4H10O2 has two singlets with an area ratio of 2 : 3.
- b. The 1H NMR spectrum of a compound with molecular formula C6H10O2 has two singlets with an area ratio of 2 : 3.
- c. The 1H NMR spectrum of a compound with molecular formula C8H6O2 has two singlets with an area ratio of 1 : 2.
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Given below are the ¹H NMR spectra of two isomeric compounds with the molecular formula C4H₂O₂.
Spectrum X
3
C₂HgO₂
11
Spectrum Y
10 9
8
0
11
10
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Using the following choices, determine which compound corresponds to which spectrum.
LOCH 3
A.
B.
C.
b
D.
C₂H₂O₂
مله
6
OH
pom
3
6
7. Which of the molecules below correspond to which of the 'H NMR spectra? Explain your choice. Note that
in both spectra below, the peaks are singlets of 3H or 9H.
FUX
18
#
3H
A
Denting 3
10 9 8 7 6 5 4
OCH 3
4
+2
9H
1
1
B
J
3H
Cada 3 2
7 6 5 4
10 9 8 7
9H
1
3. For each compound give the number of NMR signals and then determine how many peaks are
present for each NMR signal.
а.
b.
С. С
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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Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.Similar questions
- Following are two constitutional isomers with the molecular formula C4H8O2. (a) Predict the number of signals in the 1H-NMR spectrum of each isomer. (b) Predict the ratio of areas of the signals in each spectrum. (c) Show how you can distinguish between these isomers on the basis of chemical shift.arrow_forwardWhat compound gives rise to these spectra?arrow_forwardHow does the operating frequency in NMR spectroscopy compare with the operating frequency in IR and UV/Vis spectroscopy?arrow_forward
- How many lines are observed in the 13C NMR spectrum of each compound?arrow_forwardThe signals on the left of an NMR spectrum are shielded compared to the signals on the right True O Falsearrow_forwardPropose structures that are consistent with the following spectra. (Integral ratios are given from left to right across the spectrum.) a. The 1H NMR spectrum of a compound with molecular formula C4H10O2 has two singlets with integral ratios of 2 : 3. b. The 1H NMR spectrum of a compound with molecular formula C6H10O2 has two singlets with integral ratios of 2 : 3. c. The 1H NMR spectrum of a compound with molecular formula C8H6O2 has two singlets with integral ratios of 1 : 2.arrow_forward
- Answer the following questions for compounds L, M, and N drawn below. a.) How many signals are expected in the 1H NMR spectrum?b.) Into how many peaks is each signal in the 1H NMR spectrum split?c.) How many lines are expected in the 13C NMR spectrumarrow_forward1B. Can 1H NMR spectroscopy be used to differentiate between the two compounds? Briefly explain why or why not. Predict the 1H NMR spectrum for each compound (include integration, multiplicity, and approximate chemical shift). Put it in data table format.arrow_forwardDraw all constitutional isomers of molecular formula C3H6Cl2.a. How many signals does each isomer exhibit in its 1H NMR spectrum?b. How many lines does each isomer exhibit in its 13C NMR spectrum?c. When only the number of signals in both 1H and 13C NMR spectroscopy is considered, is it possible to distinguish all of these constitutional isomers?arrow_forward
- J5 I need to interpret the NMR data by correlating each peak in the spectrum to each set of hydrogens in the structure. I need help labeling each peak in the spectrum with a letter for ease of description. I need to know what the structure is and the name of the structure too!arrow_forwardDetermine the molecular structure of the compound in the IR spectrum data, 1H NMR ; 13C NMR and MS, explain it for each picture.arrow_forwardMatch the peaks in this spectrum with hydrogens on the structure below. A) H3C I H₂ 3.0 H₂ CH3 IV 2.0 ppm 1.0 1.68 ppm II: 0.99 ppm III: 2.32 ppm IV: 3.61 ppm 1: B) I: 0.99 ppm II: 1.68 ppm III: 2.32 ppm IV: 3.61 ppm C) I: II: 1.68 ppm 0.99 ppm +arrow_forward
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