Concept explainers
You have a sample of a compound of molecular formula
by two groups,
benzene isomer corresponds to these
Want to see the full answer?
Check out a sample textbook solutionChapter 17 Solutions
Organic Chemistry
- How would you use NMR (either 13C or 1H) to distinguish between the following pairs of isomers?arrow_forwardThe 13C-NMR spectrum of 3-methyl-2-butanol shows signals at 17.88 (CH3), 18.16 (CH3), 20.01 (CH3), 35.04 (carbon-3), and 72.75 (carbon-2). Account for the fact that each methyl group in this molecule gives a different signal.arrow_forwardPropose a structural formula for the analgesic phenacetin, molecular formula C10H13NO2, based on its 1H-NMR spectrum.arrow_forward
- 3-Bromo-1-phenyl-1-propene shows a complex NMR spectrum in which the vinylic proton at C2 is coupled with both the C1 vinylic proton (J = 16 Hz) and the C3 methylene protons (J = 8 Hz). Draw a tree diagram for the C2 proton signal, and account for the fact that a five-line multiplet is observed.arrow_forwardA compound with the molecular formula C4H₁1N has the following ¹H NMR spectrum, in which the relative integration values are illustrated with step curves. Which of the following is the correct number of protons giving rise to each signal? al O2H, 3H, 6H Ο 1Η, 4Η, 6Η O 2H, 4H, 5H O 3H, 4H, 5H PPMarrow_forward3. Consider the isomers A, B and C given below: CH3 CH3 CH3 Br A Br Br 2-Bromomethylbenzene 3-Bromomethylbenzene 4-Bromomethylbenzene (a) For each compound how many chemically different proton signals would you expect to see in their 'H NMR spectra? A = В - C = (b) For each proton signal identified above use the m+1 rule to determine the splitting pattern that will be observed for each proton signal of each isomer: doublet ÇH3 CH3 CH3 Br H. H Br H. H. Br A Вarrow_forward
- Which one of these four compounds would give a 13C NMR spectrum with only these three peaks, one at 210, one at 40 and one at 20? H3C OB OD 13C NMR delta (8) values C=O of ketones, aldehydes C=O of acids, esters, amides C=C and C=N C-X (where X = halogen, O) base position, alkyl C OC A OA CH3 H3C B CH3 H3C1 220-200 160-180 100-150 40-70 0 - 40 CH3 H₂C D CH3arrow_forwardQUESTION 9 Propose a structure for a carboxylic acid with molecular formula C6H10O2 by interpreting the following 13C NMR spectra.arrow_forwardA 13C NMR spectrum is shown for a molecule with the molecular formula of C5H10O2. Draw the structure that best fits this data. 180 160 140 120 100 80 60 40 20 PPMarrow_forward
- Would you expect the 1H NMR spectrum of (S)-naproxen to be different from or identical with the NMR spectrum of racemic naproxen shown in Figure 1?arrow_forwardA'H NMR spectrum is shown for a molecule with the molecular formula of CeH9Br. Draw the structure that best fits this data.arrow_forward1Compound 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_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning