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Concept explainers
(a)
Interpretation:
Whether the given compound is aromatic is to be stated.
Concept introduction:
(b)
Interpretation:
The two sets of resonances in NMR spectrum of the given compound are to be assigned. The explanation as to why there is difference in the chemical shifts is to be stated. Also, the explanation as to why one of the chemical shifts is so small is to be stated.
Concept introduction:
The number of NMR signal in a compound is equal to the number of chemically non-equivalent protons present in that compound. The more the shielded proton less will be its chemical shift value and the corresponding signal will be produced at the right-hand side or lower frequency region or vice versa.
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Chapter 16 Solutions
EBK ORGANIC CHEMISTRY
- Predict the theoretical number of different NMR signals produced by each compound, and give approximate chemical shifts. Point out any diastereotopic relationships. (a) Ph¬CHBr¬CH2Br (b) vinyl chloridearrow_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_forwardWhat is the structure of the compound which gives rise to this data? Explain your reasoning. NMR SPECTRUM C7H80arrow_forward
- Sketch the 1H NMR spectra of the following compounds.arrow_forwardThe following NMR spectra were obtained from a compound with the molecular formula C4H6O. Use this information to predict its structure.arrow_forwardDraw 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_forward
- 9. (a) A compound with chemical formula C₂H₂CIBr shows the proton NMR spectrum consisting of two doublets with J-7.3 Hz. What is the molecular structure of this compound? (b) The proton chemical shifts of the two doublets from the previous question differ by 0.3 ppm. Can you consider the proton spectrum as the first order one?arrow_forwardExplain why 2-chloropropene shows signals for three kinds of protons in its 1H NMRspectrum? Draw the structure and predict the approximate values for 1H-NMR spectra.arrow_forward(a) Draw all six isomers of formula C4H8 (including stereoisomers).(b) For each structure, show how many types of H would appear in the proton NMR spectrum.(c) For each structure, show how many types of C would appear in the 13C NMR spectrum.arrow_forward
- How would integration distinguish the 1H NMR spectra of the following compounds?arrow_forwardGive the structure that corresponds to the following molecular formula and H1 NMR spectrum:: C7H16O4: δ 1.93 (triplet); δ 3.35 (s); δ 4.49 (triplet); relative integral 1:6:1.arrow_forwardPredict the structure of a compound based on this 13C NMR spectra. The chemical formula of this compound is C4H6O2. Briefly explain your answer.arrow_forward
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