Concept explainers
A and B, isomers of molecular formula
a. Identify the structures of A and B from the following
Compound A: singlet at
Compound B: doublet at
b. What is the structure of C?
Want to see the full answer?
Check out a sample textbook solutionChapter 15 Solutions
ORGANIC CHEMISTRY
- Following are 1H-NMR spectra for compounds G, H, and I, each with the molecular formula C5H12O. Each is a liquid at room temperature, is slightly soluble in water, and reacts with sodium metal with the evolution of a gas. (a) Propose structural formulas of compounds G, H, and I. (b) Explain why there are four lines between 0.86 and 0.90 for compound G. (c) Explain why the 2H multiplets at 1.5 and 3.5 for compound H are so complex.arrow_forwardAscaridole 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_forward3-Methyl-2-butanol has five signals in its 13C NMR spectrum at 17.90, 18.15, 20.00, 35.05, and 72.75 . Why are the two methyl groups attached to C3 nonequivalent? Making a molecular model should be helpful.arrow_forward
- Isomer set #1: CH3OCCH,CH3 CH3COCH,CH3 a b Compound D, CHgO2, shows a downfield singlet in its 'H-NMR spectrum. Is it compound a or b? Isomer set #2: CH3OCCH2CH3 CH3COCH2CH3 a b. Compound D, C,H8O2, shows a downficld quartet in its 'H-NMR spectrum. Is it compound a or b?arrow_forward4. Deduce the structure of a compound with the molecular formular C8H10O that exhibits the following ¹H NMR and ¹³℃ NMR spectra. (6 pts) Proton NMR 22 7 Carbon NMR There are two. 160 unresolved lines at 130 ppm 140 120 5 Chemical Shift (ppm) 100 80 60 Chemical Shift (ppm) 40 3 20 2V 0arrow_forwardYou have a sample of a compound of molecular formula C11H15NO2, which has a benzene ring substituted by two groups, (CH3)2N – and – CO2CH2CH3, and exhibits the given 13C NMR. What disubstituted benzene isomer corresponds to these 13C data?arrow_forward
- Draw a structure for the compound, C3H5Br, that fits the following 'H NMR data: d 2.32 (3H, singlet) ô 5.35 (1H, broad singlet) ô 5.54 (1H, broad singlet) You do not have to consider stereochemistry. You do not have to explicitly draw H atoms. In cases where there is more than one answer, just draw one. C opy aste C ChemDoodlearrow_forwardAn unknown compound reacts with ethyl chloride and aluminum trichloride to form a compound that has the following 1H NMR spectrum. What is thestructure of the compound?arrow_forwardWhat is the structure of a compound of molecular formula C10H14O2 that shows a strong IR absorption at 3150–2850 cm-1 and gives the following 1H NMR absorptions: 1.4 (triplet, 6 H), 4.0 (quartet, 4 H), and 6.8 (singlet, 4 H) ppm?arrow_forward
- Choose the structure corresponding to the given 1H and 13C NMR spectraarrow_forward5. What would be different in the 1H NMR spectra of a mono and disubstituted azulene?How many signals would you expect in the 13C NMR of a mono and disubstituted azulene?arrow_forwardHow could 1H NMR spectroscopy be used to distinguish among isomers A, B, and C?arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning