Concept explainers
Deduce the structure of each of the following compounds on the basis of their
Spectra and molecular formulas:
Want to see the full answer?
Check out a sample textbook solutionChapter 14 Solutions
CAREY: ORGANIC CHEMISTRY
- 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.arrow_forwardCan you please explain the 1H NMR spectra pattern of sulfamic acid?arrow_forwardWhat are the functional groups and ppm range for the following NMR peaks?arrow_forward
- A 13 C-NMR and 1 H-NMR spectrum of C12 H 17 NO is shown below. Determine thestructure of C12 H 17 NO. There is a peak at 15.0 ppm and 15.4 ppm. There are twopeaks at 129.5 ppm.arrow_forwardWhat is the structure of an unknown compound with molecular formula C6H15N that gives the following 1H NMR absorptions: 0.9 (singlet, 1 H), 1.10 (triplet, 3 H), 1.15 (singlet, 9 H), and 2.6 (quartet, 2 H) ppm?arrow_forwardThe 1H-NMR spectrum of Compound C shows five signals – δ 2.38 (1H, dt), 2.72 (1H, dt), 5.34 (1H, t), 5.49 (2H, ddd), 6.27 (2H, dd) ppm. Its 13C-NMR spectrum has four signals – δ 26, 58, 127, 129 ppm. In the compound’s mass spectrum, the M+1 peak appears at m/z = 115. An M+2 peak, whose intensity is roughly one-third that of the M+1 peak, also appears. Suggest a structure for this compound.arrow_forward
- 1. Nomex is a flame resistant polymer developed by DuPont in the 1960s. Itis made by polymerizing benzene-1,3-diamine and isophthaloyl chloride. a) Draw three repeating units of Nomex. b) How many peaks will there be in the 1 H NMR spectrum of Nomex,assuming a polymer strand is infinitely long? c) How many peaks will there be in the 13 C NMR spectrum of Nomex,assuming a polymer strand is infinitely long?arrow_forwardHow can the signals in the 6.5 to 8.1 ppm region of their 1H NMR spectra distinguish the following compounds?arrow_forwardThe H1H1 NMR spectrum shown corresponds to an unknown compound with the molecular formula C6H10C6H10. There are no strong IR bands between 2100 and 2300 or 3250 and 3350 cm−1. Deduce and draw the structure of the molecule that corresponds to the spectrum.arrow_forward
- How could 1H NMR spectroscopy be used to distinguish between attached pair of compoundsarrow_forwardA compound used as a moth repellant has three molecular ion peaks at m/z = 146 (100%), 148 (65%) & 150 (10%) amu in its mass spectrum. A pair of smaller peaks are seen at m/z= 111 (34%) & 113 (11%). The infrared spectrum shows sharp absorption just above 3000 cm^-1 region, and also at 1480 cm^-1. The ^1 H nmr shows a single sharp signal at delta = 7.2 ppm, and the ^13 C nmr has two signals (delta = 133 & 130 ppm).arrow_forwardHow many peaks would you expect to see in the 13C NMR spectrum of 3-bromohexane? a.) 3 b.) 4 c.) 5 d.) 6arrow_forward
- Principles of Instrumental AnalysisChemistryISBN:9781305577213Author:Douglas A. Skoog, F. James Holler, Stanley R. CrouchPublisher:Cengage LearningOrganic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning