The antibiotic Prontosil, developed by Bayer Pharmaceuticals in 1932, was used in saving the life of President Roosevelt's son from severe strep throat in 1936. H2N H2N- -NH2 Prontosil Prontosil is an azo dye, which can be prepared from an aryldiazonium ion and an aromatic compound. Using the templates below, draw the structures of the diazonium ion and the coupling component for this drug. Diazonium ion Coupling component

The antibiotic Prontosil, developed by Bayer Pharmaceuticals in 1932, was used in saving the life of President Roosevelt's son from severe strep throat in 1936. H2N H2N- -NH2 Prontosil Prontosil is an azo dye, which can be prepared from an aryldiazonium ion and an aromatic compound. Using the templates below, draw the structures of the diazonium ion and the coupling component for this drug. Diazonium ion Coupling component

Organic Chemistry

8th Edition

ISBN:9781305580350

Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Chapter21: Benzene And The Concept Of Aromaticity

Section: Chapter Questions

Problem 21.26P: Compound I (C11H14O2) is insoluble in water, aqueous acid, and aqueous NaHCO3, but dissolves readily...

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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.
Enamines formed from the cyclic secondary amine pyrrolidine are important intermediates in the synthesis of 1,5-diketones. (1st pic) On the structures provided below, draw arrows showing electron flow for the reaction mechanism for the acetic acid-catalyzed formation of an enamine from cyclohexanone and pyrrolidine. (2nd pic)
One of the heptanedione isomers below has a pka of approximately 9 rather than 20. Which isomer? Why? Draw its conjugate base and offer a full explanation of its acidity.
A chemist is summoned to an abandoned waste-disposal site to determine the contents of a leaking, corroded barrel. Thebarrel reeks of an overpowering fishy odor. The chemist dons a respirator to approach the barrel and collect a sample,which she takes to her laboratory for analysis.The mass spectrum shows a molecular ion at m>z 101, and the most abundant fragment is at m>z 86. The IR spectrum shows no absorptions above 3000 cm-1, many absorptions between 2800 and 3000 cm-1, no absorptions between1500 and 2800 cm-1, and a strong absorption at 1200 cm-1. The proton NMR spectrum shows a triplet (J = 7 Hz) at d1.0and a quartet (J = 7 Hz) at d2.4, with integrals of 17 spaces and 11 spaces, respectively.(a) Show what structural information is implied by each spectrum, and propose a structure for the unknown toxic waste.(b) Current EPA regulations restrict the disposal of liquid wastes because they tend to leak out of their containers.Propose an inexpensive method for converting this…
Reaction of butanenitrile (CH3CH2CH2CN) with methylmagnesium bromide (CH3MgBr), followed by treatment with aqueous acid, forms compound G. G has a molecular ion in its mass spectrum at m/z = 86 and a base peak at m/z = 43. G exhibits a strong absorption in its IR spectrum at 1721 cm−1 and has the 1H NMR spectrum given below. What is the structure of G? We will learn about the details of this reaction in Chapter 22.
γ-Butyrolactone (C4H6O2, GBL) is a biologically inactive compound that is converted to the biologically active recreational drug GHB (Section 19.5) by a lactonase enzyme in the body. Since γ-butyrolactone is more fat soluble than GHB, it is more readily absorbed by tissues and thus produces a faster onset of physiological symptoms. γ-Butyrolactone shows an absorption in its IR spectrum at 1770 cm−1 and the following 1H NMR spectral data: 2.28 (multiplet, 2 H), 2.48 (triplet, 2 H), and 4.35 (triplet, 2 H) ppm. What is the structure of γ-butyrolactone?
Following is the structure of miconazole, the active antifungal agent in a number of over-the-counter preparations, including Monistat, that are used to treat vaginal yeast infections. One of the compounds needed for the synthesis of miconazole is the trichloro derivative of toluene shown on its right. (a) Show how this derivative can be synthesized from toluene. (b) How many stereoisomers are possible for miconazole?
10. What is the order of increase in acidity for the following compounds?
The 1H NMR spectra for two esters with molecular formula C8H8O2 are shown next. Which of the esters is hydrolyzed more rapidly in an aqueous solution with a pH of 10?
3 The 1H- and 13C-NMR data of an ester of molecular formula C6H10O2 are given below. Also shown are the COSY and HETCOR NMR spectra of the ester. Identify the ester, explaining how you reach your conclusion. 1H-NMR: 7.20-6.90 (1H), 5.85 (1H), 4.16 (2H), 1.88 (3H), 1.31 (3H) ppm 13C-NMR: 166.7, 144.5, 123.0 , 60.2, 18.0, 14.3 ppm
Furan undergoes electrophilic aromatic substitution more readily than benzene; mild reagents and conditions are sufficient.For example, furan reacts with bromine to give 2-bromofuran.(a) Propose mechanisms for the bromination of furan at the 2-position and at the 3-position. Draw the resonance forms ofeach sigma complex, and compare their stabilities.(b) Explain why furan undergoes bromination (and other electrophilic aromatic substitutions) primarily at the 2-position.O Br O123furan 2-bromofuran
Reaction of C6H5CH2CH2OH with CH3COCl affords compound W, whichhas molecular formula C10H12O2. W shows prominent IR absorptions at3088–2897, 1740, and 1606 cm−1. W exhibits the following signals in its1H NMR spectrum: 2.02 (singlet), 2.91 (triplet), 4.25 (triplet), and 7.20–7.35(multiplet) ppm. What is the structure of W?