Organic Chemistry
7th Edition
ISBN: 9780321803221
Author: Paula Y. Bruice
Publisher: Prentice Hall
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Textbook Question
Chapter 15.20, Problem 43P
Identify each compound below from its molecular formula and its 13C NMR spectrum.
- a. C11H22O
- b. C8H9Br
- c. C6H10O
- d. C6H12
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Identify the carbon atoms that give rise to the signals in the 13C NMR spectrum of each compound.
a.CH3CH2CH2CH2OH; 13C NMR: 14, 19, 35, and 62 ppm
b.(CH3)2CHCHO; 13C NMR: 16, 41, and 205 ppm
c.CH2=CHCH(OH)CH3; 13C NMR: 23, 69, 113, and 143 ppm
Identify each compound below from its molecular formula and its 13C NMR spectrum.
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
Chapter 15 Solutions
Organic Chemistry
Ch. 15.1 - Prob. 1PCh. 15.1 - Prob. 2PCh. 15.4 - How many signals would you expect to see in the 1H...Ch. 15.4 - Prob. 4PCh. 15.4 - How could you distinguish the 1H NMR spectra of...Ch. 15.4 - Draw an isomer of dichlorocyclopropane that gives...Ch. 15.5 - Prob. 7PCh. 15.5 - Prob. 8PCh. 15.5 - Prob. 9PCh. 15.5 - Where would you expect to find the 1H NMR signal...
Ch. 15.6 - Prob. 11PCh. 15.7 - Prob. 12PCh. 15.7 - Prob. 13PCh. 15.7 - Without referring to Table 14.1, label the proton...Ch. 15.8 - [18]-Annulene shows two signals in its 1H NMR...Ch. 15.9 - How would integration distinguish the 1H NMR...Ch. 15.9 - Which of the following compounds is responsible...Ch. 15.10 - Prob. 19PCh. 15.10 - Explain how the following compounds, each with the...Ch. 15.10 - The 1H NMR spectra of two carboxylic acids with...Ch. 15.11 - Draw a diagram like the one shown in Figure 14.12...Ch. 15.12 - Indicate the number of signals and the...Ch. 15.12 - How can their 1H NMR spectra distinguish the...Ch. 15.12 - Identify each compound from its molecular formula...Ch. 15.12 - Prob. 27PCh. 15.12 - Propose structures that are consistent with the...Ch. 15.12 - Describe the 1H NMR spectrum you would expect for...Ch. 15.13 - Prob. 30PCh. 15.13 - Identify the compound with molecular formula...Ch. 15.14 - Prob. 32PCh. 15.15 - a. For the following compounds, which pairs of...Ch. 15.17 - Explain why the chemical shift of the OH proton of...Ch. 15.17 - Prob. 37PCh. 15.17 - Prob. 38PCh. 15.17 - Prob. 39PCh. 15.20 - Answer the following questions for each compound:...Ch. 15.20 - Prob. 41PCh. 15.20 - How can 1,2-, 1,3-, and 1,4-dinitrobenzene be...Ch. 15.20 - Identify each compound below from its molecular...Ch. 15.22 - Prob. 44PCh. 15.22 - What does cross peak X in Figure 14.34 tell you?Ch. 15 - Prob. 46PCh. 15 - Draw a spitting diagram for the Hb proton and give...Ch. 15 - Label each set of chemically equivalent protons,...Ch. 15 - Match each of the 1H NMR spectra with one of the...Ch. 15 - Determine the ratios of the chemically...Ch. 15 - How can 1H NMR distinguish between the compounds...Ch. 15 - Prob. 52PCh. 15 - The 1H NMR spectra of three isomers with molecular...Ch. 15 - Prob. 54PCh. 15 - Prob. 55PCh. 15 - Prob. 56PCh. 15 - Compound A, with molecular formula C4H9Cl, shows...Ch. 15 - The 1H NMR spectra of three isomers with molecular...Ch. 15 - Would it be better to use 1H NMR or 13C NMR...Ch. 15 - There are four esters with molecular formula...Ch. 15 - An alkyl halide reacts with an alkoxide ion to...Ch. 15 - Identity each of the following compounds from its...Ch. 15 - Identity each of the following compounds from its...Ch. 15 - Prob. 64PCh. 15 - How can the signals in the 6.5 to 8.1 ppm region...Ch. 15 - The 1H NMR spectra of two compounds, each with...Ch. 15 - Draw a splitting diagram for the Hb proton if Jbc...Ch. 15 - Sketch the following spectra that would be...Ch. 15 - How can 1H NMR be used to prove that the addition...Ch. 15 - Identity each of the following compounds from its...Ch. 15 - Dr. N. M. Arr was called in to help analyze the 1H...Ch. 15 - Calculate the amount of energy (in calories)...Ch. 15 - The following 1H NMR spectra are four compounds,...Ch. 15 - When compound A (C5H12O) is treated with HBr, it...Ch. 15 - Identity each of the following compounds from its...Ch. 15 - Identify each of the following compounds from its...Ch. 15 - Identity the compound with molecular formula...Ch. 15 - Identify the compound with molecular formula C6H14...
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- Propose a structural formula for each compound consistent with its 1H-NMR and 13C-NMR spectra. (a) C5H10O2 (b) C7H14O2 (c) C6 H12O2 (d) C7H12O4 (e) C4H7ClO2 (f) C4H6O2arrow_forwardFollowing are 1H-NMR spectra for compounds G, H, and I, each with the molecular formula C5H12O. Each is a liquid at room temperature, is slightly soluble in water, and reacts with sodium metal with the evolution of a gas. (a) Propose structural formulas of compounds G, H, and I. (b) Explain why there are four lines between 0.86 and 0.90 for compound G. (c) Explain why the 2H multiplets at 1.5 and 3.5 for compound H are so complex.arrow_forward14. Compound B has molecular formula C9H12. It shows five signals in the 1H-NMR spectrum - a doublet of integral 6 at 1.22 ppm, a septet of integral 1 at 2.86 ppm, a singlet of integral 1 at 5.34 ppm, a doublet of integral 2 at 6.70 ppm, and a doublet of integral 2 at 7.03 ppm. The 13C-NMR spectrum of B shows six unique signals (23.9, 34.0, 115.7, 128.7, 148.9, and 157.4). Identify B and explain your reasoning.arrow_forward
- Identify the carbon atoms that give rise to the signals in the 1°C NMR spectrum of each compound. a. CH;CH,CH,CH,OH; 1°C NMR: 14, 19, 35, and 62 ppm b. (CHa)2CHCHO; 1°C NMR: 16, 41, and 205 ppm c. CH2 = CHCH(OH)CH3; 1C NMR: 23, 69, 113, and 143 ppmarrow_forwardIdentify the carbon atoms that give rise to the signals in the 13C NMR spectrum of each compound.a. CH3CH2CH2CH2OH; 13C NMR: 14, 19, 35, and 62 ppmb. (CH3)2CHCHO; 13C NMR: 16, 41, and 205 ppmc. CH2 = CHCH(OH)CH3; 13C NMR: 23, 69, 113, and 143 ppmarrow_forwardWhich molecule corresponds to the following NMR spectrum? 3H singlet 3H 2H triplet quartet 4H multiplet PPM A: B: D: O A O D O Barrow_forward
- CH3 2. An unknown isomer of C4H9Cl has the ¹³C NMR and DEPT-135 spectra shown below: 13C NMR: 90 70 |||| A 50 8 (ppm) CH3CH₂CH₂ CH₂ CI 30 10 DEPT-135: CH3 CH3-CHCH₂-CI B 90 70 Circle the compound that is represented by these spectra. Clearly explain your reasoning. you will need to explain how each of the other three isomers was eliminated from consideration. 50 8 (ppm) CH3CH₂ CH-CI CH3 C 30 10 CH3 CH3-C-CI CH3 Darrow_forward3. How many signals would you expect in the 1H and 13C NMR spectrum of each molecule? H. ethyl p-anisate (licorice) diacetyl (buttered popcorn) hexanal (tutti-fruitti) 1H 13C 1H 13C 1H 13Carrow_forward13. Which compound has four distinct signals in its 13C NMR spectrum? أن لا يا بنا I II III IV Br Varrow_forward
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