Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
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Chapter 13.SE, Problem 59GP
The mass spectrum and 13C NMR spectrum of a hydrocarbon are shown. Propose a structure for this hydrocarbon, and explain the spectral data.
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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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- 142. A mixture of H2(g) and N2(g) has a density of 0.216 g/liter at 300 K and 500 torr. What is the mole fraction composition of the mixture?arrow_forwardOne liter of N2(g) at 2.1 bar and two liters of Ar(g) at 3.4 bar are mixed in a 4.0 liter flask to form an ideal gas mixture. Calculate the value of the final pressure of the mixture if the initial and final temperature of the gases are the same. Repeat this calculation if the initial temperature of the N2(g) and Ar(g) are 304 K and 402 K, respectively, and the final temperature of the mixture is 377 K.arrow_forward10 5 4. These four 'H NMR spectra were recorded from different isomers with molecular formula CsH,CIO. They all contain a carbonyl group. Determine the structure of the different isomers. 0 10 5 0 10 5 10 9 8 7 6 5 4 3. 1 0 9 10 10 66 9 0 10 9 10 5 1 8 7 6 5 3 2 -a 8 7 6 5 1 10 9 8 7 6 5 22 2 1 0 3 2 16 1 0 3 2 1 2 6 0arrow_forward
- Use the expression below to ⚫ calculate its value and report it to the proper number of significant digits (you may need to round your answer). ⚫ calculate the % error (or % relative error or % inherent error) ⚫ calculate the absolute error. (20.54±0.02 × 0.254±0.003) / (3.21±0.05) = Value: % Error: Absolute error: ± | % (only 1 significant digit) (only 1 significant digit)arrow_forwardIn each case (more ductile, more brittle, more tough or resistant), indicate which parameter has a larger value. parameter Elastic limit Tensile strength more ductile Strain at break Strength Elastic modulus more fragile more tough or resistantarrow_forwardNonearrow_forward
- What functional groups are present in this IRarrow_forwardIn each case (more ductile, more brittle, more tough or resistant), indicate which parameter has a larger value. parameter Elastic limit Tensile strength more ductile Strain at break Strength Elastic modulus more fragile more tough or resistantarrow_forward4) A typical bottle of pop holds carbon dioxide at a pressure of 5 atm. What is the concentration of carbon dioxide in th solution? 5) A stream flowing over rocks and such is exposed to the atmosphere and well aerated. What would be the nitrogen concentration in the water at 25°C? (Air pressure is 1.000 bar.)arrow_forward
- Use the expression below to ⚫ calculate its value and report it to the proper number of significant digits (you may need to round your answer). ⚫ calculate the % error (or % relative error or % inherent error) ⚫ calculate the absolute error. (30.078±0.003) - (20.174±0.001) + (9.813±0.005) = Value: % Error: absolute error: ± % (only 1 significant digit) (only 1 significant digit)arrow_forwardDon't used Ai solution and don't used hand raitingarrow_forwardCircle the letter next to the most appropriate response. 1) Which is likely to be the least soluble with water? a) hexane b) acetone c) trichloromethane d) trinitro-toluene 2) Which is likely to be the most soluble in 3,4-dimethyloctane? a) hexane b) acetone c) trichloromethane d) trinitro-toluene 3) When ammonium nitrate is dissolved in water, the solution: a) gets warmer. b) gets colder. c) stays the same temperature. d) is none of the above because potassium nitrate is insoluble.arrow_forward
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