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Acid-catalyzed hydrolysis of
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Study Guide/Solutions Manual for Organic Chemistry
- 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_forwardAn unknown compound has a molecular formula of C4H6O2. Its IR spectrum shows absorptions at 3095, 1762, 1254, and 1118 cm -1. It exhibits the following signals in its 1H NMR spectrum (ppm): 2.12 (singlet,3H), 4.55 (doublets of doublets, 1H), 4.85 (doublet of doublets, 1H), 7.25 (doublets of doublets, 1H); and the following signals in its 13C NMR spectrum (ppm): 20.8, 100.4, 141.2, 168.0. Draw the structure of the unknown compoundarrow_forwardAnalyse the high resolution proton NMR spectrum of a compound with a molecular formula of C8H16O2 and and write its name. Options: A. 2-ethylhexanoic acid B. 1,4-cyclohexanedimethanol C. ethyl hexanoate D. butyl butyrate E. ethyl 2,2-dimethylpropanoatearrow_forward
- An unknown compound has a molecular formula of C3H6O2. Its IR spectrum shows a very strong and broad band at 2980 and a strong sharp peak at 1716 cm-1. It exhibits the following signals in its 1H NMR spectrum (ppm): 1.21 (triplet, 3H), 2.48 (quartet, 2H), 11.7 (singlet, 1H); and the following signals in its 13C NMR spectrum (ppm): 8.9, 27.6, 181.5. Draw the structure of the unknown compound.arrow_forwardTreatment of alcohol A (molecular formula C5H12O) with CrO3, H2SO4, and H2O affords B with molecular formula C5H10O, which gives an IR absorption at 1718 cm−1. The 1H NMR spectrum of B contains the following signals: 1.10 (doublet, 6 H), 2.14 (singlet, 3 H), and 2.58 (septet, 1 H) ppm. What are the structures of A and B?arrow_forwardInterpret the 1H NMR spectrum of Indole-3-Carboxaldehydearrow_forward
- As a method for the synthesis of cinnamaldehyde (3-phenyl-2-propenal), a chemist treated 3-phenyl-2-propen-1-ol with K2Cr2O7 in sulfuric acid. The product obtained from the reaction gave a signal at δ5 in its 13C NMR spectrum. Alternatively, when the chemist treated 3-phenyl-2-propen-1-ol with PCC in CH2Cl2, the 13C NMR spectrum of the product displayed a signal at δ193.8. (All other signals in the spectra of both compounds appeared at similar chemical shifts.) (a) Which reaction produced cinnamaldehyde? (b) What was the other product?arrow_forwardCiprofloxacin is a member of the fluoroquinolone class of antibiotics.(a) Which of its rings are aromatic?(b) Which nitrogen atoms are basic?(c) Which protons would you expect to appear between d 6 and d 8 in the proton NMR spectrum?arrow_forwardThe 1H-NMR spectrum of 2-(4-nitrophenyl)propanoic acid shows signals at 1.6, 4.0, 7.5, 8.2, and 12.0 ppm. Assign the correct chemical shift to each proton environment.arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning