ORGANIC CHEMISTRY-W/S.G+SOLN.MANUAL
8th Edition
ISBN: 9780134595450
Author: Bruice
Publisher: PEARSON
expand_more
expand_more
format_list_bulleted
Concept explainers
Textbook Question
Chapter 18, Problem 66P
Use the four compounds shown below to answer the following questions:
- a. Why are the ortho-halo-substituted benzoic acids stronger acids than benzoic acid?
- b. Why is o-fluorobenzoic acid the weakest of the ortho-halo-substituted benzoic acids?
- c. Why do o-chlorobenzoic acid and o-bromobenzoic acid have similar pKa values?
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solutionStudents have asked these similar questions
Use the four compounds shown below to answer the following questions:
a. Why are the ortho-halo-substituted benzoic acids stronger acids than benzoic acid?b. Why is o-fluorobenzoic acid the weakest of the ortho-halo-substituted benzoic acids?c. Why do o-chlorobenzoic acid and o-bromobenzoic acid have similar pKa values?
Use the four compounds shown below to answer the following questions:
a. Why are the ortho-halo-substituted benzoic acids stronger acids than benzoic acid? b. Why is o-fluorobenzoic acid the weakest of the ortho-halo-substituted benzoic acids? c. Why do o-chlorobenzoic acid and o-bromobenzoic acid have similar pKa values?
Although p-hydroxybenzoic acid is less acidic than benzoic acid, o-hydroxybenzoic acid is slightly more acidic than benzoic acid. Explain this result.
Chapter 18 Solutions
ORGANIC CHEMISTRY-W/S.G+SOLN.MANUAL
Ch. 18.1 - Draw the structure for each of the following: a....Ch. 18.3 - Why does hydration inactivate FeBr3?Ch. 18.6 - Prob. 4PCh. 18.7 - What is the major product of a Friedel-Crafts...Ch. 18.9 - Describe two ways to prepare each of the following...Ch. 18.10 - Prob. 7PCh. 18.11 - Name the following:Ch. 18.11 - Draw a structure for each of the following: a....Ch. 18.11 - Draw the structure for each of the following: a....Ch. 18.11 - Correct the following incorrect names: a....
Ch. 18.12 - Prob. 14PCh. 18.12 - List the compounds in each set from most reactive...Ch. 18.13 - Prob. 16PCh. 18.13 - What product(s) result from nitration of each of...Ch. 18.13 - Prob. 18PCh. 18.13 - What products are obtained from the reaction of...Ch. 18.15 - Give the products, if any, of each of the...Ch. 18.16 - a. Does a coupling reaction have to be used to...Ch. 18.16 - Show how the following compounds can be...Ch. 18.16 - Prob. 24PCh. 18.17 - What is the major product(s) of each of the...Ch. 18.17 - Prob. 26PCh. 18.18 - Why isn't FeBr3 used as a catalyst in the first...Ch. 18.18 - Prob. 29PCh. 18.18 - Write the sequence of steps required for the...Ch. 18.18 - Show how the following compounds can be...Ch. 18.19 - What product is formed from reaction of...Ch. 18.19 - Prob. 33PCh. 18.19 - Draw the structure of the activated ring and the...Ch. 18.20 - Prob. 35PCh. 18.20 - Prob. 36PCh. 18.20 - Diazomethane can be used to convert a carboxylic...Ch. 18.21 - Prob. 38PCh. 18.21 - Prob. 39PCh. 18.21 - Prob. 40PCh. 18.22 - Prob. 41PCh. 18 - Draw the structure for each of the following: a....Ch. 18 - Name the following:Ch. 18 - Prob. 44PCh. 18 - Prob. 45PCh. 18 - For each of the statements in Column I, choose a...Ch. 18 - What product is obtained from the reaction of...Ch. 18 - Draw the product(s) of each of the following...Ch. 18 - Rank the following substituted anilines from most...Ch. 18 - Prob. 50PCh. 18 - Prob. 51PCh. 18 - Show how the following compounds can be...Ch. 18 - Prob. 53PCh. 18 - The compound with the 1H NMR spectrum shown below...Ch. 18 - Rank each group of compounds from most reactive to...Ch. 18 - Prob. 56PCh. 18 - Prob. 57PCh. 18 - For each of the following components, indicate the...Ch. 18 - Prob. 59PCh. 18 - Prob. 60PCh. 18 - Describe two ways to prepare anisole from benzene.Ch. 18 - Prob. 62PCh. 18 - The following tertiary alkyl bromides undergo an...Ch. 18 - An aromatic hydrocarbon with a molecular formula...Ch. 18 - Show how the following compounds can be...Ch. 18 - Use the four compounds shown below to answer the...Ch. 18 - a. Rank the following esters from most reactive to...Ch. 18 - A mixture of 0.10 mol benzene and 0.10 mol...Ch. 18 - Prob. 69PCh. 18 - Prob. 70PCh. 18 - Benzene underwent a Friedel-Crafts acylation...Ch. 18 - Prob. 72PCh. 18 - Prob. 73PCh. 18 - Friedel-Crafts alkylations can be carried out with...Ch. 18 - Show how the following compounds can be prepared...Ch. 18 - Prob. 76PCh. 18 - Prob. 77PCh. 18 - a. Describe four ways the following reaction can...Ch. 18 - Propose a mechanism for each of the following...Ch. 18 - How can you prepare the following compounds with...Ch. 18 - Describe how naphthalene can he prepared from the...Ch. 18 - Using resonance contributors for the carbocation...Ch. 18 - Prob. 83PCh. 18 - What reagents are required to carry out the...Ch. 18 - Prob. 85PCh. 18 - Prob. 86PCh. 18 - Prob. 87PCh. 18 - Propose a mechanism for each of the following...Ch. 18 - P-Fluoronitrobenzene is more reactive toward...Ch. 18 - When heated with chromic acid, compound A forms...Ch. 18 - Show how the following compounds can be prepared...Ch. 18 - How can you distinguish the following compounds...Ch. 18 - Describe how mescaline can be synthesized from...Ch. 18 - Propose a mechanism for the following reaction...Ch. 18 - Propose a mechanism for each of the following...Ch. 18 - Describe how 3-methyl-1-phenyl-3-pentanol can he...Ch. 18 - An unknown compound reacts with ethyl chloride and...Ch. 18 - a. Explain why the following reaction leads to the...Ch. 18 - Explain why hydroxide ion catalyzes the reaction...Ch. 18 - Prob. 100PCh. 18 - Prob. 101PCh. 18 - a. How can aspirin be synthesized from benzene? b....Ch. 18 - Prob. 103PCh. 18 - Show how Novocain, a painkiller used frequently by...Ch. 18 - Prob. 105PCh. 18 - Saccharin, an artificial sweetener, is about 300...
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
- Is carvacrol more acidic or less acidic than phenol? Explain your answer.arrow_forwardCarbonyl compounds can be protonated on the carbonyl oxygen. Protonation of the carbonyl oxygen gives a species whose positive charge is delocalized by resonance. Explain why acetic acid (ethanoic acid) is more readily protonated than acetone (propanone).arrow_forwardWhich is more acidic, p-methylphenol or phenol? why? Why is water more acidic than ethanol but slightly less acidic than methanol? Explain the acidity trend of alcohols: 1>2 > 3arrow_forward
- The order of increasing acidity is Phenol < meta-cyanophenol < ortho-cyanophenol 1.how about para-cyanophenol??does it has higher acidicity than both ortho-cyanophenol and meta cyanophenol or lower?? 2.why does ortho-cyanophenol have higher acidicity than meta cyanophenol?? 3. why doesmeta cyanophenol have higher acidicity than Phenolarrow_forwardwhy pyrazole is more basic than pyridine?arrow_forward4-Cyanophenol has a pKa = 8.0, whereas phenol has a pKa= 10.0. Resonance form that best illustrates why 4-cyanophenol is more acidic isarrow_forward
- Define what is reduction reaction, reducing agents, weak and strong reducing agents sodium borohydride reduction with benzophenone and sodium borohyride to get benzophenonearrow_forwardDraw the structure of chloric and chlorous acid and predict their pKa values using Pauling's rules.arrow_forwardWhy is pyrrole more acidic than pyrrolidine?arrow_forward
- Explain why the heat of neutralization involving acetic acid and hydroxidesodium is lower than the value found in the neutralization reaction involving hydrochloric acid and the sodium hydroxide.arrow_forward1. Explain why the protonation of pyrrole occurs at C2 to form A, rather than the N atom to form B 2. Explain why compound A is more acidic than C, the conjugate acid of pyridine. :N-H H H H -H Pyrrole pKa=0.4 pKa=5.3 A B C Harrow_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
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
- Chemistry for Today: General, Organic, and Bioche...ChemistryISBN:9781305960060Author:Spencer L. Seager, Michael R. Slabaugh, Maren S. HansenPublisher:Cengage LearningOrganic 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
Chemistry for Today: General, Organic, and Bioche...
Chemistry
ISBN:9781305960060
Author:Spencer L. Seager, Michael R. Slabaugh, Maren S. Hansen
Publisher:Cengage Learning
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
IR Spectroscopy; Author: Professor Dave Explains;https://www.youtube.com/watch?v=_TmevMf-Zgs;License: Standard YouTube License, CC-BY