Concept explainers
Interpretation:
The strucutral formula of the given compound K has to be decucted with the help of the given
Concept Introduction:
The
Chemical shift: The NMR spectrum of any compound is taken with reference to a standard compound called reference compound. Generally, tetramethylsilane (TMS) is taken as the reference compound. The methyl protons of TMS are equivalent and produces only one sharp peak at the rightmost end of the scale.
13C NMR Spectroscopy: This type of NMR splitting of signals tells us numbers of hydrogens atoms are attached to each carbon. The triangle rule (n+1) C. The chemical shift explains the different hybridization
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Chapter 21 Solutions
OWLv2 with MindTap Reader, 1 term (6 months) Printed Access Card for Brown/Iverson/Anslyn/Foote's Organic Chemistry, 8th Edition
- Compound I (C11H14O2) is insoluble in water, aqueous acid, and aqueous NaHCO3, but dissolves readily in 10% Na2CO3 and 10% NaOH. When these alkaline solutions are acidified with 10% HCl, compound I is recovered unchanged. Given this information and its 1H-NMR spectrum, deduce the structure of compound I.arrow_forwardPropose a structure given the 1H and 13C NMR spectra of the unknown compound. Assign chemical shifts to corresponding hydrogen and carbon atoms Molecular Formula: C5H10O3arrow_forwardCompounds A and B are isomers having the molecular formula C4H8O3. Identify A and B on the basis of their 1H NMR spectra.Compound A: δ 1.3 (3H, triplet); 3.6 (2H, quartet); 4.1 (2H, singlet); 11.1 (1H, broad singlet)Compound B: δ 2.6 (2H, triplet); 3.4 (3H, singlet); 3.7 (2H triplet); 11.3 (1H, broad singlet)arrow_forward
- Compound B of molecular formula C9H19N shows a noteworthy infrared absorption at 3300 cm-1. Its 1H-NMR spectrum shows three singlets – δ 1.0 (6H), 1.1 (12H), 1.4 (1H) ppm. Its 13C-NMR spectrum has four signals – δ 25, 28, 41, 64 ppm. Suggest a structure for this compound.arrow_forwardUse the following spectroscopic data to work out the structure of an organic compound: Molecular formula: C3H7NO2, IR (cm): 3001, 2987, 1553 and 1387 cm*1; 1H NMR (5): 1.0 (t, 3H), 2.1 (m, 2H), and 4.4 (t, 2H); 13C NMR (5): 10, 21, and 78. MS: 89 (M+), 43 (Base peak), 41, and 29arrow_forwardThymol (molecular formula C10H14O) is the major component of the oil of thyme. Thymol shows IR absorptions at 3500–3200, 3150–2850, 1621, and 1585 cm−1. The 1H NMR spectrum of thymol is given below. Propose a possible structure for thymol.arrow_forward
- Thymol (molecular formula C10H14O) is the major component of the oil of thyme. Thymol shows IR absorptions at 3500–3200, 3150–2850, 1621, and 1585 cm–1. The 1H NMR spectrum of thymol is given below. Propose a possible structure for thymol.arrow_forwardCompound A has molecular formula C5H10O. It shows three signals in the 1H-NMR spectrum - a doublet of integral 6 at 1.1 ppm, a singlet of integral 3 at 2.14 ppm, and a quintet of integral 1 at 2.58 ppm. Suggest a structure for A and explain your reasoning.arrow_forwardCompound A of molecular formula C3H6O shows a noteworthy infrared absorption at 1716 cm-1. Its 1H-NMR spectrum shows one singlet – δ 2.2 (6H) ppm. Its 13C-NMR spectrum has two signals – δ 30, 207 ppm. Suggest a structure for this compound.arrow_forward
- Compound P has molecular formula C5H9C102. Deduce the structure of P from its 1H and 13C NMR spectra.arrow_forwardPhenacetin is an analgesic compound having molecular formula C10H13NO2. Once a common component in over-the-counter pain relievers such as APC (aspirin, phenacetin, caffeine), phenacetin is no longer used because of its liver toxicity. Deduce the structure of phenacetin from its 1H NMR and IR spectra.arrow_forwardCompound P has molecular formula C5H9ClO2. Deduce the structure of P from its 1H and 13C NMR spectra.arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage LearningIntroduction to General, Organic and BiochemistryChemistryISBN:9781285869759Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar TorresPublisher:Cengage Learning