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
Textbook Question
Chapter 10.6C, Problem 10.9P
A nitro group (—NO2) effectively stabilizes a negative charge on an adjacent carbon atom through resonance:
Two of the following nitrophenols are much more acidic than phenol itself. The third compound is only slightly more acidic than phenol. Use resonance structures of the appropriate phenoxide ions to show why two of these anions should be unusually stable.
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solutionStudents have asked these similar questions
Arrange the following molecules in increasing order of acidity. Base it only on their structural differences and explain how it is so.
1. HF, CH3CH2CH2OH, CH3CH2COOH
2. Ethyl amine, Ethanol, Propane
Write the equilibrium-constant expressions and obtainnumerical values for each constant in.
(a) the basic dissociation of aniline, C6H5NH2.
(b) the acidic dissociation of hypochlorous acid,HClO.
(c) the acidic dissociation of methyl ammoniumhydrochloride, CH3NH3Cl.
(d) the basic dissociation of NaNO2.
(e) the dissociation of H3AsO3to H3O+and AsO33-.
(f) the reaction of C2O42-with H2O to give H2C2O4and OH-.
show solution
Explain this statement: Although 2-methoxyacetic acid (CH3OCH2COOH) is a stronger acid than acetic acid (CH3COOH), p-methoxybenzoic acid (CH3OC6H4COOH) is a weaker acid than benzoic acid (C6H5COOH).
Chapter 10 Solutions
Organic Chemistry (9th Edition)
Ch. 10.3A - Prob. 10.1PCh. 10.3B - Give both the IUPAC name and the common name for...Ch. 10.3B - Prob. 10.3PCh. 10.3C - Give a systematic (IUPAC) name for each diol. a....Ch. 10.4B - Predict which member of each pair will be more...Ch. 10.4B - Dimethylamine (CH3)2NH, has a molecular weight of...Ch. 10.6A - Prob. 10.7PCh. 10.6A - Prob. 10.8PCh. 10.6C - A nitro group (NO2) effectively stabilizes a...Ch. 10.6C - Prob. 10.10P
Ch. 10.8B - Prob. 10.11PCh. 10.8B - Prob. 10.12PCh. 10.9A - Prob. 10.13PCh. 10.9B - Prob. 10.14PCh. 10.9C - Show how you would synthesize each tertiary...Ch. 10.9D - Prob. 10.16PCh. 10.9D - Show how you would add Grignard reagents to acid...Ch. 10.9D - A formate ester, such as ethyl formate, reacts...Ch. 10.9E - Prob. 10.19PCh. 10.9E - In Section9-7B, we saw how acetylide ions add to...Ch. 10.9F - Prob. 10.21PCh. 10.10A - Prob. 10.22PCh. 10.10B - Prob. 10.23PCh. 10.11B - Predict the products you would expect from the...Ch. 10.11B - Prob. 10.25PCh. 10.11B - Prob. 10.26PCh. 10.12 - Prob. 10.27PCh. 10.12 - Prob. 10.28PCh. 10.12 - Authentic skunk spray has become valuable for use...Ch. 10 - Give a systematic (IUPAC) name for each alcohol....Ch. 10 - Give systematic (IUPAC) names for the following...Ch. 10 - Draw the structures of the following compounds...Ch. 10 - Predict which member of each pair has the higher...Ch. 10 - Predict which member of each pair is more acidic,...Ch. 10 - Predict which member of each group is most soluble...Ch. 10 - Draw the organic products you would expect to...Ch. 10 - Prob. 10.37SPCh. 10 - Show how you would synthesize the following...Ch. 10 - Show how you would use Grignard syntheses to...Ch. 10 - Show how you would accomplish the following...Ch. 10 - Show how you would synthesize the following: a....Ch. 10 - Complete the following acid-base reactions. In...Ch. 10 - Prob. 10.43SPCh. 10 - Prob. 10.44SPCh. 10 - Geminal diols, or 1,1-diols, are usually unstable,...Ch. 10 - Vinyl alcohols are generally unstable, quickly...Ch. 10 - Compound A (C7H11Br) is treated with magnesium in...Ch. 10 - Prob. 10.48SPCh. 10 - Prob. 10.49SPCh. 10 - Prob. 10.50SPCh. 10 - Prob. 10.51SPCh. 10 - Prob. 10.52SPCh. 10 - Prob. 10.53SPCh. 10 - Prob. 10.54SPCh. 10 - Prob. 10.55SPCh. 10 - Prob. 10.56SPCh. 10 - Show how this 1 alcohol can be made from the...Ch. 10 - Prob. 10.58SPCh. 10 - Prob. 10.59SPCh. 10 - Prob. 10.60SP
Additional Science Textbook Solutions
Find more solutions based on key concepts
For each of the following 2-dimensional shapes, determine the highest order rotation axis of symmetry.
Inorganic Chemistry
45. Calculate the mass of nitrogen dissolved at room temperature in an 80.0-L home aquarium. Assume a total pre...
Chemistry: Structure and Properties
The active ingredient in Tylenol and a host of other over-the-counter pain relievers is acetaminophen (C8H9NO2)...
Chemistry: Atoms First
Label each statement about the polynucleotide ATGGCG as true or false. The polynucleotide has six nucleotides. ...
General, Organic, & Biological Chemistry
Calculate the lattice energy of CaCl2 using a Born-Haber cycle and data from Appendices F and L and Table 7.5. ...
Chemistry & Chemical Reactivity
What is the pH range for acidic solutions? For basic solutions?
Introduction to Chemistry
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
- Arrange these compounds in order of increasing acidity: 2,4-dichlorophenol, phenol, cyclohexanol.arrow_forwardNucleophilic aromatic substitution provides one of the common methods for making phenols. Show how you would synthesize the following phenols, using benzene or toluene as your aromatic starting material, and explain why mixtures of products would be obtained in some cases.(a) p-nitrophenol (b) 2,4,6-tribromophenol (c) p-chlorophenolarrow_forwardElectrophilic aromatic substitution usually occurs at the 1-position of naphthalene, also called the a position. Predict the major products of the reactions of naphthalene with the following reagents.(a) isobutylene and HF (b) cyclohexanol and BF3 (c) fuming sulfuric acidarrow_forward
- Electrophilic aromatic substitution usually occurs at the 1-position of naphthalene, also called the a position. Predict the major products of the reactions of naphthalene with fuming sulfuric acid.arrow_forwarda. Compound X is benzene, Y is acetic anhydride acid. Complete the following scheme and determine Z! b. Determine which reagents except acetic acid anhydrides can replace Y!arrow_forwardArrange the following compounds in the increasing order of their acid strength: p-cresol, p-nitrophenol, phenolarrow_forward
- Give an explanation, why the acidity of these phenolic derivatives give these pKa value? Describe it by using the electronic effect on the acidity.arrow_forwardChemical Equilibrium Write the equilibrium-constant expressions and obtain numerical values for each constant in (a) the basic dissociation of aniline, C6H5NH2. (b) the acidic dissociation of hypochlorous acid, HClO. (c) the acidic dissociation of methyl ammonium hydrochloride, CH3NH3Cl. (d) the basic dissociation of NaNO2. (e) the dissociation of H3AsO3 to H3O+ and AsO33- Using step-by-step processarrow_forwardAccount for the fact that one carboxyl group is a considerably stronger acid than the other carboxyl group.arrow_forward
- Arrange these compounds in order of increasing acidity: 2,4-dichlorophenol, phenol, cyclohexanol.arrow_forward(a) Although phenoxide ion has more number of resonating structures than carboxylate ion, carboxylic acid is a stronger acid than phenol. Give two reasons.(b) How will you bring about the following converstions?(i) Propanone to propane (ii) Benzoyl chloride to benzaldehyde(iii) Ethanal to but-2-enalarrow_forwardwrite acid-base reactions using NaOH/HCI and your acidic/basic compound (benzoic acid/p-toluidine). Is your neutral compound (9-fluorenone) acid/base reactive? explainarrow_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
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning
Alcohols, Ethers, and Epoxides: Crash Course Organic Chemistry #24; Author: Crash Course;https://www.youtube.com/watch?v=j04zMFwDeDU;License: Standard YouTube License, CC-BY