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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The DEPT-90 spectrum exhibits
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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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- How many unique signals in HNMR will this compound have? Can you draw them out so I can see?arrow_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_forwardHow would you use infrared spectroscopy to distinguish between the following pairs of constitutional isomers? and CH3CH₂C=CH (a) CH3C=CCH3 (b) 0 || CH3CCH=CHCH3 (c) H₂C=CHOCH 3 and and 0 || CH3CCH₂CH=CH₂ CH3CH2CHOarrow_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_forwardFor each of the following molecular structures, circle each of the stereocenters (if any) that the molecule has then write the number corresponding to the same (# of stereocenters) in the box provided.arrow_forward4. Which of the following compounds has the lowest carbonyl stretching frequency?arrow_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_forwardne aromatic compounds below predict the number of signals that would appear in the MR spectrum. NH2 NH2 CH3 „NH2 CH "NO NO2 NO2 1.arrow_forwardPropanone and 2-propen-1-ol are constitutional isomers. Show how to distinguish between them by IR spectroscopy. CH-C-CH, CH,— CH—CН, — ОН Propanone (Acetone) 2-Propen-1-ol (Allyl alcohol)arrow_forwardPart A Draw C4HgBr₂ that has the following ¹H NMR spectrum: 1.97 (s, 3H), 3.89 (s, 1H). Hint: Draw C4H₁0 (there are two isomers), and then replace two H atoms with Br atoms. NOTE NOTE! C4H8Br2 has 8 H's! But the integral is 3H and 1H!!! How will you fix that? Draw the molecule on the canvas by choosing buttons from the Tools (for bonds), Atoms, and Advanced Template toolbars. The single bond is active by default. H 12D EXP L CONT 1arrow_forwardHow many groups of chemically equivalent protons exist in the following compound? (Give a number) H.arrow_forward2. How many distinct types of protons exist on the compounds below? ex H.arrow_forwardarrow_back_iosSEE MORE QUESTIONSarrow_forward_ios
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