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Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
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Textbook Question
Chapter 13.9, Problem 16P
How could you use 1H NMR to determine the regiochemistry of electrophilic addition to
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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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- Following is a balanced equation for the allylic bromination of propene. CH2==CHCH3 + Br2 h CH2==CHCH2Br + HBr (a) Calculate the heat of reaction, H 0, for this conversion. (b) Propose a pair of chain propagation steps and show that they add up to the observed stoichiometry. (c) Calculate the H 0 for each chain propagation step and show that they add up to the observed H 0 for the overall reaction.arrow_forwardAnswer choices for question 1: A B C D Answer choices for question 2: E F G Harrow_forwardDefine Protons on Benzene Rings ?arrow_forward
- The 200- MHz ¹H NMR spectrum of 2-propanal (shown) has three distinctive resonances: 89.5 (1H, singlet), 2.2 (2H, quartet), 1.0 (3H, triplet) Part A Assign each resonance to the structure. 2.2 2H q 9.5 1.H S 1.0 3H H O CH₂CH3 Resetarrow_forwardThe following ¹H NMR spectrum is shown in two questions. "nmrsim presentation" 1 1 C:\Bruker TopSpin3.5p17\examdata 10 1,4-Disubstituted benzene ring Which functional group is BEST attributed to the pair of doublets at about 7-8 ppm, each integrating to 2H? trans-alkene Cyclohexene Carboxylic acid [ppm] 1,3-Disubstituted benzene ring [oa]arrow_forward09:28 Is the following compound aromatic or not? choose the correct answer (with motive) from the options given O A. It has 8 TT electrons and satisfy Huckel's rule therefore it is aromatic O B. It is aromatic with electrons 10 TT electrons and satisfy Huckel's rule OC It is not aromatic because the total number of electrons and does not satisfy Huckel's rule O D. It has 6 TI electrons, therefore it does not satisfiy Huckel's rule Add a caption... > Status (Custom)arrow_forward
- A sample of edible oil was subjected to analysis using mass spectrometry (MS). The following mass spectra (X and Y) were obtained. The spectra represent 2,4-decadienal and squalene. Identify the spectrum of 2,4-decadienal and squalene and explain your answer.arrow_forwardEthers can be prepared by reaction of an alkoxide or phenoxide ion with a primary alkyl halide. Draw the structure of the expected organic product of the reaction of iodoethane with the following alkoxide ion: H3C CH3 + Na You do not have to consider stereochemistry. You do not have to explicitly draw H atoms. Do not include lone pairs in your answer. They will not be considered in the grading. • Do not include counter-ions, e.g., Na", I, in your answer. P opy aste [*arrow_forwardExplain how the following compounds, each with the same molecular formula, could be distinguished by their 1H NMR spectra.arrow_forward
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