Organic Chemistry As a Second Language: Second Semester Topics
4th Edition
ISBN: 9781119110651
Author: David R. Klein
Publisher: WILEY
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Chapter 2.3, Problem 2.6P
The following compound has three carbonyl groups. Rank them in order of increasing wavenumber in an IR spectrum:
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Describe the 1H NMR spectrum of each compound. State how many NMR signals are present, the splitting pattern for each signal, and the approximate chemical shift
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.
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?
Chapter 2 Solutions
Organic Chemistry As a Second Language: Second Semester Topics
Ch. 2.3 - For each of the following compounds, determine...Ch. 2.3 - For each of the following compounds, determine...Ch. 2.3 - For each of the following compounds, determine...Ch. 2.3 - For each of the following compounds, determine...Ch. 2.3 - The following compound has three carbonyl groups....Ch. 2.4 - Predict which of the following C=C bonds will...Ch. 2.4 - The C=C bond in the following compound produces an...Ch. 2.5 - For each IR spectrum below, identify whether it is...Ch. 2.5 - For each IR spectrum below, identify whether it is...Ch. 2.5 - For each IR spectrum below, identify whether it is...
Ch. 2.5 - For each IR spectrum below, identify whether it is...Ch. 2.5 - For each IR spectrum below, identify whether it is...Ch. 2.5 - For each IR spectrum below, determine whether it...Ch. 2.5 - For each IR spectrum below, determine whether it...Ch. 2.5 - For each IR spectrum below, determine whether it...Ch. 2.5 - For each IR spectrum below, determine whether it...Ch. 2.5 - For each IR spectrum below, determine whether it...Ch. 2.5 - For each IR spectrum below, determine whether it...Ch. 2.5 - For each IR spectrum below, determine whether it...Ch. 2.6 - Prob. 2.22P
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- Which compound gives a signal in the 1H-NMR spectrum with a larger chemical shift, furan or cyclopentadiene? Explain.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_forwardDescribe the number of signals and their splitting in the 1H NMR spectrum of (CH3)2CHOCH3. A) 3 signals: 2 doublets and a septet B) 2 signals: a doublet and a septet C) 3 signals: a doublet, a quartet, and a septet D) 4 signals: 2 doublets, a singlet, and a septet E) 3 signals: a singlet, a doublet, and a septetarrow_forward
- Following are two constitutional isomers with the molecular formula C4H8O2. (a) Predict the number of signals in the 1H-NMR spectrum of each isomer. (b) Predict the ratio of areas of the signals in each spectrum. (c) Show how you can distinguish between these isomers on the basis of chemical shift.arrow_forwardThe following 1H NMR peaks were recorded on a spectrometer operating at 200 MHz. Convert each into δ units. (a) CHCl3; 1454 Hz (b) CH3Cl; 610 Hz (c) CH3OH; 693 Hz (d) CH2Cl2; 1060 Hzarrow_forwardWhen the 1HNMR spectrum of an alcohol is run in dimethylsulfoxide (DMSO) solvent rather than in chloroform, exchange of the Ο-H proton is slow and spin-spin splitting is seen between the Ο-H proton and C-H protons on the adjacent carbon. What spin multiplicities would you expect for the hydroxyl protons in the following alcohols? (a) 2-Methyl-2-propanol (b) Cyclohexanol (c) Ethanol (d) 2-Propanol (e) Cholesterol (f) 1-Methylcyclohexanolarrow_forward
- 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_forwardThe 1H NMR spectrum of CH3OH recorded on a 500 MHz NMR spectrometer consists of two signals, one due to the CH3 protons at 1715 Hz and one due to the OH proton at 1830 Hz, both measured downfield from TMS. (a) Calculate the chemical shift of each absorption. (b) Do the CH3 protons absorb upfield or downfield from the OH proton?arrow_forwardWhat is the structure of the compound in the following ¹H-NMR spectrum with the molecular formula C9H10O₂? Relative integration is shown. HO₂C CO₂H CO₂H CHO CO₂H PPM 2arrow_forward
- 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.arrow_forwardThe 1H NMR spectrum of CH3OH recorded on a 500 MHz NMR spectrometer consists of two signals, one due to the CH3 protons at 1715 Hz and one due to the OH proton at 1830 Hz, both measured downeld from TMS. (a) Calculate the chemical shift of each absorption. (b) Do the CH3 protons absorb upeld or downeld from the OH proton?arrow_forwardAssign NMR peaks to the following molecule:arrow_forward
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