Organic Chemistry (9th Edition)
9th Edition
ISBN: 9780321971371
Author: Leroy G. Wade, Jan W. Simek
Publisher: PEARSON
expand_more
expand_more
format_list_bulleted
Concept explainers
Videos
Textbook Question
Chapter 16.12, Problem 16.22P
Ciprofloxacin 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 δ6 and δ8 in the proton NMR spectrum?
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solution
Students have asked these similar questions
The pKa for Molecule A is 10 units lower than Molecule B.
Molecule A
Draw conjugate base of A
:B
H H
pKa = 10
Molecule B
Draw conjugate base of B
OCH3
:B
H H
pКa 3 20
Please provide a brief explanation for the difference in pKa of these to molecules.
Draw the H1 NMR spectra of ethylcyclopropane. Draw the chemical structure and predict the proton splitting and chemical shifts.
Based on the structures given below, which of the following statements is entirely true?
N
Quinoline
NH
Isoquinoline Indole
Isoindole
All four compounds are non-aromatic, with 12 pi-electrons each and are equal in basicity.
All four compounds are aromatic, with 10 pi-electrons each and are equal in basicity.
Only quinoline and isoquinoline having 10 pi-electrons each are aromatic while indole and isoindole are antiaromatic having 8 pi-electrons each.
All four compounds are aromatic, with 10 pi-electrons each, and with quinoline and isoquinoline being stronger bases than indole and isoindole.
The nitrogen atoms of quinoline and isoquinoline are sp2 hybridized while the nitrogen atoms of indole and isoindole are sp³ hybridized
Previous
Chapter 16 Solutions
Organic Chemistry (9th Edition)
Ch. 16.2 - Prob. 16.1PCh. 16.2 - Prob. 16.2PCh. 16.2 - a. Draw the resonance forms of benzene,...Ch. 16.2 - Show the product of the Diels-Alder dimerization...Ch. 16.4 - Prob. 16.5PCh. 16.6 - Make a model of cyclooctatetraene in the tub...Ch. 16.6 - Prob. 16.7PCh. 16.6 - Prob. 16.8PCh. 16.7 - Prob. 16.9PCh. 16.8A - a. Draw the molecular orbitals for the...
Ch. 16.8A - Repeat Problem16-10 for the cyclopentadienyl ions....Ch. 16.8C - Explain why each compound or ion should be...Ch. 16.8C - The following hydrocarbon has an unusually large...Ch. 16.8C - Prob. 16.14PCh. 16.8C - Prob. 16.15PCh. 16.9B - Prob. 16.16PCh. 16.9C - Show which of the nitrogen atoms in purine are...Ch. 16.9C - The proton NMR spectrum of 2-pyridone gives the...Ch. 16.9D - Prob. 16.19PCh. 16.9D - Prob. 16.20PCh. 16.10 - Prob. 16.21PCh. 16.12 - Ciprofloxacin is a member of the fluoroquinolone...Ch. 16.13 - Draw and name all the chlorinated benzenes having...Ch. 16.13 - Name the following compounds:Ch. 16.15 - The UV spectrum of 1-phenylprop-2-en-1-ol shows an...Ch. 16 - Prob. 16.26SPCh. 16 - Name the following compounds:Ch. 16 - Draw and name all the methyl, dimethyl, and...Ch. 16 - Four pairs of compounds are shown. In each pair,...Ch. 16 - One of the following hydrocarbons is much more...Ch. 16 - In Kekuls time cyclohexane was unknown, and there...Ch. 16 - Prob. 16.32SPCh. 16 - Azulene is a deep-blue hydrocarbon with resonance...Ch. 16 - Prob. 16.34SPCh. 16 - Prob. 16.35SPCh. 16 - Prob. 16.36SPCh. 16 - Prob. 16.37SPCh. 16 - Prob. 16.38SPCh. 16 - Prob. 16.39SPCh. 16 - Biphenyl has the following structure. a. Is...Ch. 16 - Anions of hydrocarbons are rare, and dianions of...Ch. 16 - How would you convert the following compounds to...Ch. 16 - Prob. 16.43SPCh. 16 - Prob. 16.44SPCh. 16 - A student found an old bottle labeled thymol on...Ch. 16 - Prob. 16.46SPCh. 16 - Prob. 16.47SPCh. 16 - Prob. 16.48SPCh. 16 - The proton NMR chemical shifts of the hydrogens in...Ch. 16 - Prob. 16.50SPCh. 16 - NMR has been used to probe many molecular...
Knowledge Booster
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.Similar questions
- What do you mean by carbon acid? What is the range of their pKa's?arrow_forwardBased on the structures given below, which of the following statements is entirely true? Quinoline NH Isoquinoline Indole Isoindole All four compounds are non-aromatic, with 12 pi-electrons each and are equal in basicity. Only quinoline and Isoquinoline having 10 pi-electrons each are aromatic while indole and isoindole are antiaromatic having 8 pi-electrons each The nitrogen atoms of quinoline and isoquinoline are sp2 hybridized while the nitrogen atoms of indole and isoindole are sp³ hybridized. All four compounds are aromatic, with 10 pi-electrons each and are equal in basicity. All four compounds are aromatic, with 10 pi-electrons each, and with quinoline and isoquinoline being stronger bases than indole and isoindarrow_forwardIdentify the most and the least acidic compound in each of the following sets. Leave the remaining answer in each set blank. a) 2,4-dinitrobenzoic acid: v p-nitrobenzoic acid: p-bromobenzoic acid: b) benzoic acid: v formic acid: v propanoic acid: c) cyclohexanol: v phenol: v benzoic acid:arrow_forward
- Propose a structural formula for each compound consistent with its 1H-NMR and 13C-NMR spectra. (a) C5H10O2 (b) C7H14O2 (c) C6 H12O2 (d) C7H12O4 (e) C4H7ClO2 (f) C4H6O2arrow_forwardHow would you use NMR (either 13C or 1H) to distinguish between the following pairs of isomers?arrow_forwardFollowing are 1H-NMR spectra for compounds G, H, and I, each with the molecular formula C5H12O. Each is a liquid at room temperature, is slightly soluble in water, and reacts with sodium metal with the evolution of a gas. (a) Propose structural formulas of compounds G, H, and I. (b) Explain why there are four lines between 0.86 and 0.90 for compound G. (c) Explain why the 2H multiplets at 1.5 and 3.5 for compound H are so complex.arrow_forward
- Phenacetin, a substance formerly used in over-the-counter headache remedies, has the formula C10H13NO2. Phenacetin is neutral and does not dissolve in either acid or base. When warmed with aqueous NaOH, phenacetin yields an amine, C8H11NO, whose 1H NMR spectrum is shown. When heated with HI, the amine is cleaved to an aminophenol, C6H7NO. What is the structure of phenacetin, and what are the structures of the amine and the aminophenol?arrow_forwardLook at NMR and answer #2,3 and 4arrow_forwardCompound A has molecular formula C7H7X. Its ¹H-NMR spectrum shows a singlet at 2.26 ppm and two doublets, one at 6.95 ppm and one at 7.28 ppm. The singlet has an integral of three and the doublets each have an integral of two. Its 13C- NMR shows five signals. The mass spectrum of A shows a peak at m/z 170 and another peak at m/z = 172; the relative height of the two peaks is 1:1 respectively. - Identify what atom X is, explaining your reasoning - Identify Compound A, explaining your reasoning Compound A is treated with a mixture of nitric and sulfuric acids to generate Compound B. The ¹H-NMR spectrum of B shows two singlets, one at 2.52 pm and one at 8.13 ppm. The 13C-NMR spectrum of B shows five signals. The mass spectrum of B shows a peak at m/z = 260 and another peak at m/z = 262; the relative height of the two peaks is 1:1 respectively. - Identify compound B, explaining your reasoning Compound B is treated with sodium ethoxide to generate compound C. The ¹H-NMR spectrum of C shows…arrow_forward
- Use the observed 1H NMR data to decide whether C and its dianion are aromatic, antiaromatic, or not aromatic. C shows NMR signals at –4.25 (6 H) and 8.14–8.67 (10 H) ppm. The dianion of C shows NMR signals at –3 (10 H) and 21 (6 H) ppm. Why are the signals shifted upeld (or downeld) to such a large extent?arrow_forward1. 4-Methylphenol is more acidic than ethanol (pKa 10.36 vs 16.0), even though both contain an OH group and a methyl group. Draw the structures of the anions formed from loss of the alcoholic protons from both compounds. Use resonance to explain the difference in their respective acidities. OH and CH,CH,-OH CHarrow_forward24. The 1HNMR spectrum of an unknown acid has the following peaks: 12.71 ppm (1H, S); 8.04 ppm (2H, d); 7.30 ppm (2H, d); 2.41 ppm (3H, s) Which structure best fits this spectral information? Dlan OH A B علی مود C OH D OHarrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning
Organic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage Learning
EBK A SMALL SCALE APPROACH TO ORGANIC LChemistryISBN:9781305446021Author:LampmanPublisher:CENGAGE LEARNING - CONSIGNMENT
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning
Organic Chemistry: A Guided Inquiry
Chemistry
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Cengage Learning
EBK A SMALL SCALE APPROACH TO ORGANIC L
Chemistry
ISBN:9781305446021
Author:Lampman
Publisher:CENGAGE LEARNING - CONSIGNMENT
NMR Spectroscopy; Author: Professor Dave Explains;https://www.youtube.com/watch?v=SBir5wUS3Bo;License: Standard YouTube License, CC-BY