Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
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Textbook Question
Chapter 13.SE, Problem 27VC
How many electronically nonequivalent kinds of protons and how many kinds of carbons are present in the following compound? Don’t forget that cyclohexane rings can ring-flip.
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Predict the multiplicity of the circled protons in a proton NMR spectrum.
triplet
singlet
quartet
quintet
doublet
H₂
O
The DEPT-90 spectrum exhibits
6
in the 0-50 ppm region
The DEPT-135 spectrum exhibits
x
100 ppm region that is a
positive ▾
C6
signal(s) for the CH groups:
▼
1,2,6
✓
in the sp2 hybridized region 100-150
C3 and C4 ▼
signal(s) (only the quaternary carbon atoms,
signal(s), indicating the presence of a methylene group (CH₂) attached to an oxygen atom,
are missing); there is
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C1 and C2 ▼
and
signal(s) in the 50-
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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- In this p nmr Is this triplet of quartet or quartet of triplet?arrow_forward2arrow_forward1) Indicate chemically equivalent nuclei (e.g. Ha, Hb, Hc). 2) Estimate the chemical shifts on the following hydrogens. CH₂ OCH₂ O CH₂0 Br CH3-CH-CH₂-CH3 CH3 OH CH3-C-C=C-H CH3 C=C-H O H CH3 Br-C-C-CH3 H Brarrow_forward
- Why is there no coupling between the a and c protons or between the b and c protons in the cis and trans alkenes shown in Figurearrow_forwardCH3 2. An unknown isomer of C4H9Cl has the ¹³C NMR and DEPT-135 spectra shown below: 13C NMR: 90 70 |||| A 50 8 (ppm) CH3CH₂CH₂ CH₂ CI 30 10 DEPT-135: CH3 CH3-CHCH₂-CI B 90 70 Circle the compound that is represented by these spectra. Clearly explain your reasoning. you will need to explain how each of the other three isomers was eliminated from consideration. 50 8 (ppm) CH3CH₂ CH-CI CH3 C 30 10 CH3 CH3-C-CI CH3 Darrow_forwardSelect all the compounds that exhibits a proton spectrum with only one signal. 2,2-dimethylpropane 1,1-dichloroethane propanone propane cyclopentane 1,2-dichloroethane | benzene | Tetra methyl silane 1,4-dimethylbenzenearrow_forward
- Give structures for the following compounds based on the spectra given. Explain your logic.arrow_forwardHow many groups of chemically equivalent protons exist in the following compound? (Give a number)arrow_forward3. Look at the two spectra below, one of which is 2-methylcyclohexanol and one of which is 3methylcyclohexene. Which spectrum belongs to which compound? Explain your reasoning. 10- 4000 200 3500 3000 2500 1500 1000 600 Spectrum A 90 20 30 20 10 500 3000 2500 2000 1600 1000 500 Vieters kn1 Spectrum Barrow_forward
- 71. Which of (a)-(d) indicates the correct order of carbon chemical shifts of the four carbons of the following compound. II CH2=CH-C-0-CH3 C3 C2 C1 Сме А. СМе < С2 < С3 <С1 В. СМе <С3 < С2 < C1 C. CMe < C2 < C1 < C3 D. СМearrow_forward125 ppm 138 ppm 153 ppm 130 ppm The chemical shifts of two carbon atoms are given for the molecules shown here. It appears that the addition of the OH group increases the chemical shift of the C atom to which it is attached, but that it decreases the chemical shift of the C atom on the opposite side. How do you account for these observations? Hint: Draw all of the pertinent resonance structures. CH3 Но -CH3arrow_forwardEach of the IR spectra below corresponds to one of the aromatic compounds listed below. Determine the molecule that corresponds to each spectrum.arrow_forwardarrow_back_iosSEE MORE QUESTIONSarrow_forward_ios
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