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Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
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Textbook Question
Chapter 13.SE, Problem 35AP
The following compounds all show a single line in their 1H NMR spectra. List them in order of expected increasing chemical shift: CH4, CH2Cl2, cyclohexane, CH3COCH3, H2C=CH2, benzene
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Chapter 13 Solutions
Organic Chemistry
Ch. 13.1 - Prob. 1PCh. 13.1 - Prob. 2PCh. 13.2 - Prob. 3PCh. 13.3 - The following 1H NMR peaks were recorded on a...Ch. 13.3 - When the 1Η NMR spectrum of acetone, CH3COCH3, is...Ch. 13.4 - Each of the following compounds has a single 1H...Ch. 13.4 - Identify the different types of protons in the...Ch. 13.5 - How many peaks would you expect in the 1H NMR...Ch. 13.6 - Predict the splitting patterns you would expect...Ch. 13.6 - Draw structures for compounds that meet the...
Ch. 13.6 - The integrated 1H NMR spectrum of a compound of...Ch. 13.7 - Identify the indicated sets of protons as...Ch. 13.7 - How many kinds of electronically nonequivalent...Ch. 13.7 - How many absorptions would you expect (S)-malate,...Ch. 13.8 - 3-Bromo-1-phenyl-1-propene shows a complex NMR...Ch. 13.9 - How could you use 1H NMR to determine the...Ch. 13.11 - Prob. 17PCh. 13.11 - Propose structures for compounds that fit the...Ch. 13.11 - Prob. 19PCh. 13.12 - Prob. 20PCh. 13.12 - Prob. 21PCh. 13.12 - Prob. 22PCh. 13.13 - Prob. 23PCh. 13.SE - Into how many peaks would you expect the 1H NMR...Ch. 13.SE - How many absorptions would you expect the...Ch. 13.SE - Sketch what you might expect the 1H and 13C NMR...Ch. 13.SE - How many electronically nonequivalent kinds of...Ch. 13.SE - Identify the indicated protons in the following...Ch. 13.SE - Prob. 29APCh. 13.SE - Prob. 30APCh. 13.SE - When measured on a spectrometer operating at 200...Ch. 13.SE - Prob. 32APCh. 13.SE - Prob. 33APCh. 13.SE - How many types of nonequivalent protons are...Ch. 13.SE - The following compounds all show a single line in...Ch. 13.SE - Prob. 36APCh. 13.SE - Propose structures for compounds with the...Ch. 13.SE - Predict the splitting pattern for each kind of...Ch. 13.SE - Predict the splitting pattern for each kind of...Ch. 13.SE - Identify the indicated sets of protons as...Ch. 13.SE - Identify the indicated sets of protons as...Ch. 13.SE - The acid-catalyzed dehydration of...Ch. 13.SE - How could you use 1H NMR to distinguish between...Ch. 13.SE - Propose structures for compounds that fit the...Ch. 13.SE - Propose structures for the two compounds whose 1H...Ch. 13.SE - Prob. 46APCh. 13.SE - How many absorptions would you expect to observe...Ch. 13.SE - Prob. 48APCh. 13.SE - How could you use 1H and 13C NMR to help...Ch. 13.SE - How could you use 1H NMR, 13C NMR, and IR...Ch. 13.SE - Assign as many resonances as you can to specific...Ch. 13.SE - Assume that you have a compound with the formula...Ch. 13.SE - The compound whose 1H NMR spectrum is shown has...Ch. 13.SE - The compound whose 1H NMR spectrum is shown has...Ch. 13.SE - Propose structures for compounds that fit the...Ch. 13.SE - Long-range coupling between protons more than two...Ch. 13.SE - The 1H and 13C NMR spectra of compound A, C8H9Br,...Ch. 13.SE - Propose structures for the three compounds whose...Ch. 13.SE - The mass spectrum and 13C NMR spectrum of a...Ch. 13.SE - Compound A, a hydrocarbon with M+=96 in its mass...Ch. 13.SE - Propose a structure for compound C, which has...Ch. 13.SE - Prob. 62GPCh. 13.SE - Propose a structure for compound E, C7H12O2, which...Ch. 13.SE - Compound F, a hydrocarbon with M+=96 in its mass...Ch. 13.SE - 3-Methyl-2-butanol has five signals in its 13C NMR...Ch. 13.SE - A 13C NMR spectrum of commercially available...Ch. 13.SE - Carboxylic acids (RCO2H) react with alcohols (ROH)...Ch. 13.SE - Prob. 68GPCh. 13.SE - The proton NMR spectrum is shown for a compound...Ch. 13.SE - The proton NMR spectrum of a compound with the...Ch. 13.SE - The proton NMR spectrum is shown for a compound...
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- How many different 13C-absorption lines and how many 'H- resonances (disregard splitting and assume that solvent exchange of acidic hydrogens does NOT take place) are observed in the spectrum of each of the following compounds? (H3C)3C-C(CH3)2 CI A H3C (H3C)3C B CH3 CH3 H₂C= -COOH C CH-CI H3C-C-CH Cl Br Darrow_forwardPredict the number of signals in the 1H-NMR spectrum of each isomer.arrow_forwardThe 1H and 13C NMR for a compound with the formula C5H12O are shown. Determine the structure of this compound. Assign the peaks: assign “a” to the most shielded hydrogen(s) in your structure, “b” to next-most shielded, etc; use capital letters for carbons).arrow_forward
- Compound A has molecular formula C8H18. It shows one singlet in the ¹H-NMR spectrum. Identify A and explain your reasoning. For the toolbar, press ALT+F10 (PC) or ALT+FN+F10 (Mac). BIUS Paragraph V Arial = = = = +8HE {} X² X₂ PR хо 23 V 10pt >¶ ¶< - ABC :3 v V ✓ Ev AV ¶T "Ω Θ I 用く x B Q ► 8. Earrow_forwardIndicate two basic differences that exist between the spectra of 1H y 13C in NMR.arrow_forwardBelow is the ¹H NMR spectrum of a constitutional (structural) isomer of C9H100, with the integration given above each peak. In addition to other peaks not given here, the IR spectrum of the isomer showed a strong peak at 1700 cm-1 Determine which of the structures given below the spectrum matches the ¹H NMR spectrum. H₂C 2 8 A C 3 CH3 CH 3 to B D Ho PPM CH3 =CH₂ 2 3arrow_forward
- In the 1H NMR spectra of 2-bromopropane (CH3)2CHBr and 1-bromopropane CH3CH2CH2Br, how many signals do you expect to see?arrow_forwardThe 1H-NMR spectrum of ethanol shows a triplet at 1.23 ppm, a singlet at 2.61 pm, and a quartet at 3.69 ppm. Assign each signal to the protons it corresponds to in the molecule. Explain the splitting pattern observed for each signal.arrow_forwardWhen the 1î-NMR spectrum of acetone, CH3COCH3, is recorded on an instrument operating at 200 MHz, a single sharp resonance at 2.1î is seen. (a) How many hertz downfield from TMS does the acetone resonance correspond to? (b) If the 1î-NMR spectrum of acetone were recorded at 500 MHz, what would the position of the absorption be in î units? (c) How many hertz downfield from TMS does this 500 MHz resonance correspond to?arrow_forward
- The number of peaks in the ¹H-NMR spectrum of a com-pound depends on the number of different kinds (environments)of H atoms. How many peaks appear in the spectrum of each iso-mer of C₄H₁₀and of C₅H₁₂arrow_forwardCompound 1 has molecular formula C7H15Cl. 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 compound 1, explaining how you reach your conclusion.arrow_forwardBelow is the ¹H NMR spectrum of a constitutional (structural) isomer of C9H100, with the integration given above each peak. In addition to other peaks not given here, the IR spectrum of the isomer showed a strong peak at 1700 cm-1 Determine which of the structures given below the spectrum matches the 1H NMR spectrum. H3C 5 A C CH3 CH3 HO B D PPM CH3 CH ₂ 2 FM N 3arrow_forward
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