Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
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Chapter 13.5, Problem 8P
How many peaks would you expect in the 1H NMR spectrum of 1, 4-dimethyl- benzene (para-xylene, or p-xylene)? What ratio of peak areas would you expect on integration of the spectrum? Refer to Table 13-3 for approximate chemical shifts, and sketch what the spectrum would look like. (Remember from
Section 2-4
that
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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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- 14- Mention the number of peaks in the 1H NMR spectrum of 1,4-dimethyl-benzene(para-xylene or p-xylene). Show and draw the exact location of the aromatic ac thealiphatic hydrogens.15- Draw the 1H NMR spectrum of Ethyl bromide or 1-Bromoethane. Show the splittingindicating which is singlet, which is doublet, etc.arrow_forwardConsider the proton NMR spectrum of styrene and splitting trees for the H* and H protons. SOH2 SOHZ ++++++ OHz SOH2 ++++ H H° C=C 6.78 6.66 5.18 5.66 $28 s.18 10 9 6. 1 8 (ppm) FIGURE 13-31 Proton NMR spectrum of styrene. 85.65 8 6.6 shift of H chemical shift of H = 17 Hz Jah = 17 Hz Je = 1.4 Hz Jo = 11 Hz c=11 Hz Part A Draw a splitting tree, similar to those for H" and H", for proton H in styrene. Drag the appropriate labels to their respective targets. Reset Help 2.3 5.16 85.58 Jac = 21 Joc = OI 1.4 11 Hzarrow_forwardThe following are all 1H-NMR spectra for compounds D, E, and F with C6H12 molecular formulas. BR2 is easily bleached in the solution. Suggest a structural equation for Compounds D, E, and F and explain the cracking form of the signal.arrow_forward
- The 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_forward13. Use the chemical formula and the 1H NMR spectrum to determine the structure of the molecule. You must show your work (Le draw fragments)| 20 + 2 - H- X + N degrees of unsaturation C4H7CIO 2 The 13C NMR contains a signal at 205 ppm. | = 3 singlet | = 2 triplet |= 2 triplet 3 8 (ppm) final answerarrow_forwardHow many signals would you expect to observe in the 1H -NMR spectrum of 2,3-dimethyl-1,3-cyclopentadiene? What would be the multiplicity (splitting) of each signal?arrow_forward
- Show the calculation step by step.arrow_forwardDescribe the 1H-NMR spectrum of 4-bromoaniline (chemical shift, integration, multiple). Make a table and describe the results.arrow_forwardWould it be better to use 1H NMR or 13C NMR spectroscopy to distinguish 1-butene, cis-2-butene, and 2-methylpropene? Explain your answer.arrow_forward
- Explain why 2-chloropropene shows signals for three kinds of protons in its 1H NMRspectrum? Draw the structure and predict the approximate values for 1H-NMR spectra.arrow_forwardTHIS CAN NOT BE HAND DRAWN! MUST BE DIGITALLY ILLUSTRATED OR USE A PC PROGRAM TO DO SO!arrow_forwardA sample of tert-butyl bromide (2-bromo-2-methyl propane) has been contaminated with some methyl bromide. The NMR spectrum of this sample shows two signals, one at 1.8 ppm and one at 2.2 ppm, corresponding to these two compounds respectively. The integrals of the two signals equate to 6:1 respectively. What is the mole percent of each compound in the mixture, or phrasing it another way, what percentage of the mixture is tert-butyl bromide and what percentage is methyl bromide? Your objective is to answer this question, explaining how you reach your decision.arrow_forward
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