ORGANIC CHEMISTRY-EBOOK>I<
9th Edition
ISBN: 9781305084414
Author: McMurry
Publisher: INTER CENG
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Chapter 13.SE, Problem 60GP
Compound A, a hydrocarbon with M+=96 in its mass spectrum, has the 13C spectral data given below. On reaction with BH3, followed by treatment with basic H2O2. A is converted into B, whose, 13C spectral data are also given below. Propose structures for A and B.
Compound A
Broadband-decoupled l3C NMR: 26.8, 28.7, 35.7, 106.9, 149.7 δ DEPT-90: no peaks DEPT-135: no positive peaks; negative peaks at 26.8, 28.7, 35.7, 106.9 δ
Compound B
Broadband-decoupled 13C NMR: 26.1, 26.9, 29.9, 40.5, 68.2 δ DEPT-90: 40.5 δ
DEPT-135: positive peak at 40.5 δ; negative peaks at 26.1, 26.9. 29.9, 68.2 δ
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15. Compound A, a hydrocarbon with M* = 96 in its mass spectrum, has the ¹³C spectral data given
below. On reaction with BH3 followed by treatment with basic H₂O2, A is converted into
compound B, whose ¹³C spectral data are also given below. Propose structures for A and B.
Compound A
Broadband-decoupled ¹³C NMR: 26.8; 28.7; 35.7; 106.9; 149.7 8
DEPT-90: no peaks
DEPT 135: no positive peaks; negative peaks at: 26.8; 28.7; 35.7; 106.9 8
Compound B
Broadband-decoupled ¹³C NMR: 26.1; 26.9; 29.9; 40.5; 68.2 8
DEPT-90: 40.5 8
DEPT-135: positive peaks at 40.5 8; negative peaks at: 26.1; 26.9; 29.9; 68.2 8
Compound A is a hydrocarbon with a molar mass of 96g/mol, with the given C13 spectral data. When compound A reacts with BH3 followed by the treatment with basic H2O2 it is converted to compound B. Propose structures for A and B, explain your analysis.Compound A- Proton decoupled C NMR: 26.8, 28.7, 35.7, 106.9, 149.7 δ.DEPT-90: No peak.DEPT-135: No positive peaks; negative peaks at 26.8, 28.7, 35.7, 106.9 δ.Compound B- Proton decoupled C NMR: 26.1, 26.9, 29.9, 40.5, 68.2 δ.DEPT-90: 40.5 δ.DEPT-135: positive peak at 40.5 δ; negative peaks at 26.1, 26.9, 29.9, 68.2 δ
Compound E (C,H,0,) is a neutral solid. Its mass spectrum shows a molecular ion
at mlz 138 and prominent peaks at M-1 and M - 17. Following are IR and 'H-NMR
spectra of compound E. Deduce the structure of compound E.
Micrometers
14 15
2.5
100
8
10
12
13
20
90
80
70
60
50
40
30
20
10
Compound E
4000
3600
3200
2800
2400
2000
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1400
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Wavenumber (cm-1)
Transmittance (%)
Chapter 13 Solutions
ORGANIC CHEMISTRY-EBOOK>I<
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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