EBK ORGANIC CHEMISTRY
8th Edition
ISBN: 8220102744127
Author: Bruice
Publisher: PEARSON
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Chapter 14.12, Problem 29P
Propose 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 C4Hl0O2 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.
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Propose 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.
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
ppm
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
Find how many peaks will appear in the proton (1H) NMR spectrum and carbon (13C) NMR spectrum of each molecue. Don't take into account splitting in the proton(1H) NMR
Chapter 14 Solutions
EBK ORGANIC CHEMISTRY
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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- 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 1arrow_forwardAssign each peak with the number in the molecular formula. Explanations will very much be appreciated.arrow_forwardDraw the structure for a compound with the formula C8H10O3 that exihibits the 1H-NMR spectrum provided integral parts are also provided in a table above the 1H-NMR picture.arrow_forward
- 13C NMR is a technique in which the total number of signals represents the number of unique carbon atoms in a molecule. Propose a structure that is consistent with the following data. a. The IR includes peaks at 1603 and 1495 cm-1. b. The 13C NMR has a total of 7 signals. c. The compound has one acidic proton.arrow_forwardHow many signals are present in the 1H NMR spectrum for each molecule? What splitting is observed in each signal?arrow_forwardAnswer 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 spectrum?arrow_forward
- Which of the C.H140 isomers above fits the following NMR spectrum best? 3H. s 6H. d 2H. d 2H. d 1H, septet LS 19 Which of the C0H140 isomers above fits the following NMR spectrum best? 3H, S 3H. I 2H. t 2H 2H. overlapping d and t 1H t sextet 1H. d 3.0 4.5 13 25 20 1arrow_forwardCan I have help with this?arrow_forwardUsing NMR to draw the kind of spectrum you would expect for each of the following compounds....arrow_forward
- 7. Determine the structure of the compounds below from their spectroscopy data. Sketch the 'H-NMR spectra of the following a and b compounds. Assign peaks to the structures. a) C3H10 1.2 8 (3H, triplet) 2.6 8 (2H, quartet) 7.1 8 (5H, broad singlet) b) C4H7BrO 2.11 8 (3H, singlet) 3.52 8 (2H, triplet) 4.40 8 (2H, triplet) Cs Scanned with CamScannerarrow_forwardPlease, I want the solution, not the solution method. Please, after a few hour I will submit the assignment ..the question is match the spectrum with the following compoundarrow_forwardFor the following compound draw the expected H-NMR and the C-NMR spectrums. On your drawing label the peaks a-g.arrow_forward
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