9th Edition

ISBN: 9781305080485

Author: John E. McMurry

Publisher: Cengage Learning

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Textbook Question

Chapter 13.SE, Problem 56GP

Long-range coupling between protons more than two carbon atoms apart is sometimes observed when π bonds intervene. An example is found in 1-methoxy-l-buten-3-yne. Not only does the acetylenic proton, Î—_a, couple with the vinylic proton H_b, it also couples with the vinylic proton H_c, four carbon atoms away. The data are:

Chapter 13.SE, Problem 56GP, Long-range coupling between protons more than two carbon atoms apart is sometimes observed when

Construct tree diagrams that account for the observed splitting patterns of Î—_a, H_b, and H_c.

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Chapter 13.SE, Problem 55GP

Chapter 13.SE, Problem 57GP

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Chapter 13 Solutions

Organic Chemistry

Ch. 13.1 - Prob. 1P Ch. 13.1 - Prob. 2P Ch. 13.2 - Prob. 3P Ch. 13.3 - The following 1H NMR peaks were recorded on a...Ch. 13.3 - When the 1Î— 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. 17P Ch. 13.11 - Propose structures for compounds that fit the...Ch. 13.11 - Prob. 19P Ch. 13.12 - Prob. 20P Ch. 13.12 - Prob. 21P Ch. 13.12 - Prob. 22P Ch. 13.13 - Prob. 23P Ch. 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. 29AP Ch. 13.SE - Prob. 30AP Ch. 13.SE - When measured on a spectrometer operating at 200...Ch. 13.SE - Prob. 32AP Ch. 13.SE - Prob. 33AP Ch. 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. 36AP Ch. 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. 46AP Ch. 13.SE - How many absorptions would you expect to observe...Ch. 13.SE - Prob. 48AP Ch. 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. 62GP Ch. 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. 68GP Ch. 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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Solution Summary: The author explains how the splitting pattern for each of the three signals is predicted. The coupling constant depends on the kind of neighboring protons involved.

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Chapter 13 Solutions