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
- 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_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_forwardDraw 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_forward
- An unkown compound, which is insoluable in water but soluble in 10% aqueous sodium bicarbonate, yielded the given 1H NMR spectrum. What is the compound?arrow_forwardIsomer 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_forward
- You 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_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_forwardHow can 1H NMR distinguish between the compounds in the following pairs?arrow_forward
- Compounds C and D are isomers with a molecular formula of CsH100 that give a negative Tollens' test. Compound C has two (2) peaks in the 'H NMR spectrum, while compound D has four (4) peaks. i) Propose the structures of compounds C and D. ii) Sketch a predicted 'H NMR spectrum of compound D with the estimated chemical shifts and multiplicity. iii) State the number of peaks for compound C in the 13C NMR spectrum. iv) Suggest a suitable chemical test to differentiate between compounds C and D. Explain the observation.arrow_forwardHow could 1H NMR spectroscopy be used to distinguish among isomers A, B, and C?arrow_forwardHow could 1H NMR spectroscopy be used to distinguish between each pair of compounds?arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning