Organic Chemistry
8th Edition
ISBN: 9781305580350
Author: William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher: Cengage Learning
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Chapter 13, Problem 13.26P
Ascaridole is a natural product that has been used to treat intestinal worms. Explain why the two methyls on the isopropyl group in ascaridole appear in its 1H-NMR spectrum as four lines of equal intensity, with two sets of two each separated by 7 Hz.
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Compound 1 has molecular formula C7H16. It shows three signals in the 1H-NMR spectrum, one at 0.85 ppm, one at 1.02 ppm, and one at 1.62 ppm. The relative integrals of these three signals are 6, 1, and 1, respectively.
Compound 2 has molecular formula C7H14. It shows three signals in the 1H-NMR spectrum, one at 0.98 ppm, one at 1.36 ppm, and one at 1.55 ppm. The relative integrals of these three signals are 3, 2, and 2, respectively.
Propose structures for compounds 1 and 2, explaining how you reach your conclusion.
The 1H NMR spectrum of 1,2-dimethoxyethane (CH3OCH2CH2OCH3) recorded on a 300 MHz NMR spectrometer consists of signals at 1017 Hz and 1065 Hz downeld from TMS. (a) Calculate the chemical shift of each absorption. (b) At what frequency would each absorption occur if the spectrum were recorded on a 500 MHz NMR spectrometer?
Compound 1 has molecular formula C6H12. It shows three signals in the 1H-NMR spectrum, one at 0.96 ppm, one at 2.03 ppm, and one at 5.33 ppm. The relative integrals of these three signals are 3, 2, and 1, respectively.
Compound 2 has molecular formula C7H15Br. It shows two signals in the 1H-NMR spectrum, one at 1.08 ppm and one at 1.59 ppm. The relative integrals of these two signals are 3 and 2, respectively.
Propose structures for compounds 1 and 2, explaining how you reach your conclusion.
Chapter 13 Solutions
Organic Chemistry
Ch. 13.2 - Calculate the ratio of nuclei in the higher spin...Ch. 13.5 - State the number of sets of equivalent hydrogens...Ch. 13.5 - Each compound gives only one signal in its 1H-NMR...Ch. 13.6 - The line of integration of the two signals in the...Ch. 13.7 - Following are two constitutional isomers with the...Ch. 13.8 - Following are pairs of constitutional isomers....Ch. 13.10 - Following is a 1H-NMR spectrum of 2-butanol....Ch. 13.11 - Explain how to distinguish between the members of...Ch. 13 - Prob. 13.9PCh. 13 - Prob. 13.10P
Ch. 13 - Prob. 13.11PCh. 13 - Following are structural formulas for three...Ch. 13 - Following arc structural formulas for the cis...Ch. 13 - Prob. 13.14PCh. 13 - Following are three compounds with the molecular...Ch. 13 - Following are 1H-NMR spectra for compounds D, E,...Ch. 13 - Following are 1H-NMR spectra for compounds G, H,...Ch. 13 - Propose a structural formula for compound J,...Ch. 13 - Compound K, molecular formula C6H14O, readily...Ch. 13 - Compound M, molecular formula C5H10O, readily...Ch. 13 - Following is the 1H-NMR spectrum of compound O,...Ch. 13 - Treatment of compound P with BH3 followed by...Ch. 13 - The 1H-NMR spectrum of compound R, C6H14O,...Ch. 13 - Write structural formulas for the following...Ch. 13 - Prob. 13.25PCh. 13 - Ascaridole is a natural product that has been used...Ch. 13 - The 13C-NMR spectrum of 3-methyl-2-butanol shows...Ch. 13 - Prob. 13.28P
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Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.Similar questions
- 1Compound 1 has molecular formula C7H16. It shows three signals in the 1H-NMR spectrum, one at 0.85 ppm, one at 1.02 ppm, and one at 1.62 ppm. The relative integrals of these three signals are 6, 1, and 1, respectively. Compound 2 has molecular formula C7H14. It shows three signals in the 1H-NMR spectrum, one at 0.98 ppm, one at 1.36 ppm, and one at 1.55 ppm. The relative integrals of these three signals are 3, 2, and 2, respectively. Propose structures for compounds 1 and 2, explaining how you reach your conclusion.arrow_forwardA'2 The 'H-NMR spectra of cyclohexanol and cyclohexanone are given below. Identify which spectrum belongs to which compound and assign the peaks in each spectrum that substantiate your decision.arrow_forwardThe 'H NMR spectrum of 1,2-dimethoxyethane (CH;OCH,CH2OCH3) recorded on a 300 MHz NMR spectrometer consists of signals at 1017 Hz and 1065 Hz downfield from TMS. (a) Calculate the chemical shift of each absorption. (b) At what frequency would each absorption occur if the spectrum were recorded on a 500 MHz NMR spectrometer?arrow_forward
- I have an NMR spectrum. There are 5 peaks. There is a doublet at 9.6 ppm (integrates to 2H) where aldehydes usually arise, don't know why there is a doublet. There is another doublet at 6.8 ppm, again integrating to 2H. There is a singlet at 4.5 ppm, integrating to 1H. There is a quartet at 3.4 ppm integrating to 2H, and lastly there is triplet at 1.2 ppm integrating to 3H. i recofnize the ethyl group but don't understand the peak at 9.6 unless it is not an aldehyde.arrow_forwardWhen the 1î-NMR spectrum of acetone, CH3COCH3, is recorded on an instrument operating at 200 MHz, a single sharp resonance at 2.1î is seen. (a) How many hertz downfield from TMS does the acetone resonance correspond to? (b) If the 1î-NMR spectrum of acetone were recorded at 500 MHz, what would the position of the absorption be in î units? (c) How many hertz downfield from TMS does this 500 MHz resonance correspond to?arrow_forwardThe 1H NMR spectrum of 1,2-dimethoxyethane (CH3OCH2CH2OCH3) recorded on a 300 MHz NMR spectrometer consists of signals at 1017 Hz and 1065 Hz downfield from TMS.(a) Calculate the chemical shift of each absorption. (b) At what frequency would each absorption occur if the spectrum were recorded on a 500 MHz NMR spectrometer?arrow_forward
- Draw the structural formulas of the following compounds and indicate the number of NMR signals that would be expected for each compound. (a) methyl iodide (b) 2,4-dimethylpentane (c) cyclopentane (d) propylene (propene)arrow_forwardCompound 1 has molecular formula C7H15Cl. It shows two signals in the 1H-NMR spectrum, one at 1.08 ppm and one at 1.59 ppm. The relative integrals of these two signals are 3 and 2, respectively. Propose structures for compound 1, explaining how you reach your conclusion.arrow_forwardIn the 1H NMR spectra of 2-bromopropane (CH3)2CHBr and 1-bromopropane CH3CH2CH2Br, how many signals do you expect to see?arrow_forward
- Ascaridole is a natural product that has been used to treat intestinal worms. Explain why the two methyls on the isopropyl group in ascaridole appear in its 'H-NMR spectrum as four lines of equal intensity, with two sets of two each separated by 7 Hz. Ascaridolearrow_forwardFollowing is the 1H-NMR spectrum of compound O, molecular formula C7H12. Compound O reacts with bromine in carbon tetrachloride to give a compound with the molecular formula C7H12Br2. The 13C-NMR spectrum of compound O shows signals at d 150.12, 106.43, 35.44, 28.36, and 26.36. Deduce the structural formula of compound O.arrow_forwardThe 'H NMR spectrum of compound A (C3H100) has four signals: a multiplet at 8 = 7.25-7.32 ppm (5 H), a singlet at d = 5.17 ppm (1 H), a quartet at d = 4.98 ppm (1 H), and a doublet at ô = 1.49 ppm (3 H). There are 6 signals in its 13C NMR spectrum. The IR spectrum has a broad absorption in the -3200 cm-1 region. Compound A reacts with KMNO4 in a basic solution followed by acidification to give compound B with the molecular formula C7H6O2. Draw structures for compounds A and B.arrow_forward
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