Organic Chemistry
8th Edition
ISBN: 9781305580350
Author: William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher: Cengage Learning
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Chapter 21, Problem 21.26P
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.
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Compounds 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)
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Chapter 21 Solutions
Organic Chemistry
Ch. 21.2 - Construct a Frost circle for a planar...Ch. 21.2 - Which compound gives a signal in the 1H-NMR...Ch. 21.2 - Prob. 21.3PCh. 21.2 - Prob. 21.4PCh. 21.3 - Prob. 21.5PCh. 21.4 - Arrange these compounds in order of increasing...Ch. 21.4 - Prob. AQCh. 21.4 - Prob. BQCh. 21.4 - Prob. CQCh. 21.5 - Prob. 21.7P
Ch. 21 - Name the following compounds and ions.Ch. 21 - Prob. 21.9PCh. 21 - Draw a structural formula for each compound. (a)...Ch. 21 - Molecules of 6,6-dinitrobiphenyl-2,2-dicarboxylic...Ch. 21 - Following each name is the number of Kekul...Ch. 21 - Prob. 21.13PCh. 21 - Prob. 21.14PCh. 21 - Prob. 21.15PCh. 21 - Which of the molecules and ions given in Problem...Ch. 21 - Prob. 21.17PCh. 21 - Naphthalene and azulene are constitutional isomers...Ch. 21 - Prob. 21.19PCh. 21 - Prob. 21.20PCh. 21 - Following are IR and 1H-NMR spectra of compound D....Ch. 21 - Compound E (C8H10O2) is a neutral solid. Its mass...Ch. 21 - Following are 1H-NMR and 13C-NMR spectral data for...Ch. 21 - Following are 1H-NMR and 13C-NMR spectral data for...Ch. 21 - Compound H (C8H6O3) gives a precipitate when...Ch. 21 - Compound I (C11H14O2) is insoluble in water,...Ch. 21 - Propose a structural formula for compound J...Ch. 21 - Propose a structural formula for the analgesic...Ch. 21 - Prob. 21.29PCh. 21 - Prob. 21.30PCh. 21 - Given here are 1H-NMR and 13C-NMR spectral data...Ch. 21 - Prob. 21.32PCh. 21 - Prob. 21.33PCh. 21 - Prob. 21.34PCh. 21 - Arrange the molecules and ions in each set in...Ch. 21 - Prob. 21.36PCh. 21 - Prob. 21.37PCh. 21 - From each pair, select the stronger base.Ch. 21 - Prob. 21.39PCh. 21 - Prob. 21.40PCh. 21 - Prob. 21.41PCh. 21 - Prob. 21.42PCh. 21 - Following is an equation for iodination of...Ch. 21 - Prob. 21.44PCh. 21 - Prob. 21.45PCh. 21 - Prob. 21.46PCh. 21 - When warmed in dilute sulfuric acid,...Ch. 21 - In the chemical synthesis of DNA and RNA, hydroxyl...Ch. 21 - Prob. 21.49PCh. 21 - Write the products of the following sequences of...Ch. 21 - Prob. 21.51PCh. 21 - Show how to convert 1-phenylpropane into the...Ch. 21 - Prob. 21.53PCh. 21 - Cromolyn sodium, developed in the 1960s, has been...Ch. 21 - Prob. 21.55PCh. 21 - Prob. 21.56PCh. 21 - Prob. 21.57PCh. 21 - Prob. 21.58PCh. 21 - Prob. 21.59PCh. 21 - Prob. 21.60PCh. 21 - Prob. 21.61PCh. 21 - Prob. 21.62PCh. 21 - Prob. 21.63PCh. 21 - Following is a synthesis for toremifene, a...
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