Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
expand_more
expand_more
format_list_bulleted
Concept explainers
Question
Chapter 10.SE, Problem 46AP
Interpretation Introduction
Interpretation:
Carboxylic acids (RCO2H; pKa ≈ 5) are approximately 1011 times more acidic than alcohols (ROH; pKa ≈ 16). In other words using the concept of resonance the observation that a carboxylate (RCO2-) ion is more stable than alkoxide (RO-) ion is to be explained.
Concept introduction:
Carboxylic acids are more acidic since their conjugate bases obtained by the loss of a proton, carboxylate anions, are stablised by resonance. Alcohols are less acidic as there is no resonance stabilization possible in their conjugate bases, the alkoxide ions.
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solutionStudents have asked these similar questions
The presence of a pi bond also makes a compound a base. With this in mind, draw the conjugate acid of ethylene, CH2=CH2.
Briefly, but clearly, explain why the –OH hydrogen in acetic acid (CH3CO2H) is more acidic than in ethanol (C2H5OH).
The acid-catalyzed hydrolysis of an ester converts an
ester into a carboxylic acid. Although there are two O
atoms that can be protonated, the first step in the
mechanism is believed to be protonation of the oxygen
in the C=0 group. Based on charge stability, why is it
favorable to protonate that oxygen? Hint: Draw out the
products of each protonation.
+ Hо
HO,
НО
Carboxylic
acid
Ester
Alcohol
Chapter 10 Solutions
Organic Chemistry
Ch. 10.1 - Prob. 1PCh. 10.1 - Draw structures corresponding to the following...Ch. 10.2 - Prob. 3PCh. 10.2 - Taking the relative reactivities of 1°, 2°, and...Ch. 10.4 - Prob. 5PCh. 10.4 - The major product of the reaction of...Ch. 10.4 - Prob. 7PCh. 10.5 - Prob. 8PCh. 10.6 - Prob. 9PCh. 10.6 - How might you replace a halogen substituent by a...
Ch. 10.7 - How would you carry out the following...Ch. 10.8 - Rank both sets of compounds in order of increasing...Ch. 10.8 - Tell whether each of the following reactions is an...Ch. 10.SE - Prob. 14VCCh. 10.SE - Prob. 15VCCh. 10.SE - Prob. 16VCCh. 10.SE - Draw the electron-pushing mechanism for each...Ch. 10.SE - Draw the electron-pushing mechanism for the...Ch. 10.SE - The formation of Br2 from NBS first involves the...Ch. 10.SE - In light of the fact that tertiary alkyl halides...Ch. 10.SE - Alkyl halides can be reduced to alkanes by a...Ch. 10.SE - Name the following alkyl halides:Ch. 10.SE - Prob. 23APCh. 10.SE - Draw and name all of the monochlorination products...Ch. 10.SE - How would you prepare the following compounds,...Ch. 10.SE - Prob. 26APCh. 10.SE - A chemist requires a large amount of...Ch. 10.SE - What product(s) would you expect from the reaction...Ch. 10.SE - What product(s) would you expect from the reaction...Ch. 10.SE - What product would you expect from the reaction of...Ch. 10.SE - Rank the compounds in each of the following series...Ch. 10.SE - Which of the following compounds have the same...Ch. 10.SE - Tell whether each of the following reactions is an...Ch. 10.SE - Prob. 34APCh. 10.SE - Alkylbenzenes such as toluene (methylbenzene)...Ch. 10.SE - Prob. 36APCh. 10.SE - Prob. 37APCh. 10.SE - Prob. 38APCh. 10.SE - Prob. 39APCh. 10.SE - Prob. 40APCh. 10.SE - The syntheses shown here are unlikely to occur as...Ch. 10.SE - Why do you suppose its not possible to prepare a...Ch. 10.SE - Prob. 43APCh. 10.SE - Identify the reagents a–c in the following...Ch. 10.SE - Prob. 45APCh. 10.SE - Prob. 46APCh. 10.SE - Prob. 47APCh. 10.SE - The relative rate of radical bromination is...Ch. 10.SE - Prob. 49APCh. 10.SE - Predict the product and provide the entire...
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
- a) If the pH value of an aqueous solution of trimethylamine [(CH3) 3N] is 10.75, what should be the molarity of this solution? (CH3) 3N + H2O ↔ (CH3) 3NH + + OH-, Kb = 6.3 × 10-5 b) What will be the pH of the solution prepared by dissolving 8.35 g of aniline hydrochloride (C6H5NH3 + Cl-) in 750 mL of 0.215 M aniline (C6H5NH2)? Is this solution an effective buffer? Explain (Kb = 7.4 × 10-10 for aniline, C: 12.0 g / mol, H: 1.0 g / mol, N: 14.0 g / mol, Cl: 35.4 g / mol) .arrow_forwarda) If the pH value of an aqueous solution of trimethylamine [(CH3)3N] is 10.75, what should be the molarity of this solution? (CH3)3N + H2O ↔ (CH3)3NH+ + OH-, Kb = 6,3 × 10-5 b) What will be the pH of the solution prepared by dissolving 8.35 g of aniline hydrochloride (C6H5NH3+Cl-) in 750 mL of 0.215 M aniline (C6H5NH2)? Is this solution an effective buffer? Explain (Kb = 7,4 × 10-10 for aniline, C: 12.0 g / mol, H: 1.0 g / mol, N: 14.0 g / mol, Cl: 35.4 g / mol) .arrow_forwardWould the carboxyl group make the 3rd option the most acidic? Or would the fluorines make the 5th one the most acidic?arrow_forward
- Use resonance forms of the conjugate bases to explain why methanesulfonic acid (CH3SO3H,pKa = -2.6) is a much stronger acid than acetic acid (CH3COOH, pKa = 4.8).arrow_forward6. (Chapter 15-Q37) Indole is an aromatic heterocyclic that has a benzene ring fused to a pyrrole ring. Answer the following questions. Indole 6(a) What is the hybridization of N in this molecule? = 6(b) How many pi electrons N contributes to the ring? = 6() Which orbitals contribute to form a sigma bond between N and H in this molecule? = 6(c) What is the electronic relationship of Indole to naphthalene? Give the answer by comparing number of rings and number of pi electrons in both compounds, write x rings, y pi electrons=|arrow_forwardThe compound WH2(C5H5)2 acts as a base, but TaH3(C5H5)2does not. Explain.arrow_forward
- Given 4-methylhexanoic acid1. How will the acid be deprotonated if the pH in the solution is adjusted so that the pH> pKa? 2. How will the acid be deprotonated if the pH in the solution is adjusted so that the pH = pKa? 3. How will the acid be deprotonated if the pH the solution is adjusted so that pH <pKa?arrow_forwardKetones typically have a pka of approximately 20. While this is certainly not a strong acid it is much stronger than a typical alkane sp3-CH. using acetone as an example, explain why ketones are much more acidic than Alkanes.arrow_forward6. Predict the position of the equilibrium and calculate the equilibrium constant, Keq, for the following acid-base reaction. CH3NH₂+ + CH3COO- CH3NH₂ + CH3COOH methylamine acetic acid acetate ion pK₂ = 4.74 methylammonium ion pK₂ = 10.64arrow_forward
- An amine R. However, when an imine is protonated, the resulting iminium ion is highly electrophilic: R An ammonium ion An imine R. R R An iminium ion Explain this difference in reactivity between an ammonium ion and an iminium ion. O The ammonium ion is a stronger acid, making it less electrophilic. • The iminium ion has a resonance structure with an empty p orbital on the carbon atom, making it electrophilic. The pi bond in the iminium ion is electron-rich, making it more electrophilic.. O The iminium ion is resonance-stabilized, making it more reactive.arrow_forwardHow does resonance affect the acidity of a compound? Why is phenol more acidic in some alcohols and why is carboxylic acid more acidic?arrow_forward+ Br₂ what is/are the products?arrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
- ChemistryChemistryISBN:9781305957404Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCostePublisher:Cengage LearningChemistryChemistryISBN:9781259911156Author:Raymond Chang Dr., Jason Overby ProfessorPublisher:McGraw-Hill EducationPrinciples of Instrumental AnalysisChemistryISBN:9781305577213Author:Douglas A. Skoog, F. James Holler, Stanley R. CrouchPublisher:Cengage Learning
- Organic ChemistryChemistryISBN:9780078021558Author:Janice Gorzynski Smith Dr.Publisher:McGraw-Hill EducationChemistry: Principles and ReactionsChemistryISBN:9781305079373Author:William L. Masterton, Cecile N. HurleyPublisher:Cengage LearningElementary Principles of Chemical Processes, Bind...ChemistryISBN:9781118431221Author:Richard M. Felder, Ronald W. Rousseau, Lisa G. BullardPublisher:WILEY
Chemistry
Chemistry
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Cengage Learning
Chemistry
Chemistry
ISBN:9781259911156
Author:Raymond Chang Dr., Jason Overby Professor
Publisher:McGraw-Hill Education
Principles of Instrumental Analysis
Chemistry
ISBN:9781305577213
Author:Douglas A. Skoog, F. James Holler, Stanley R. Crouch
Publisher:Cengage Learning
Organic Chemistry
Chemistry
ISBN:9780078021558
Author:Janice Gorzynski Smith Dr.
Publisher:McGraw-Hill Education
Chemistry: Principles and Reactions
Chemistry
ISBN:9781305079373
Author:William L. Masterton, Cecile N. Hurley
Publisher:Cengage Learning
Elementary Principles of Chemical Processes, Bind...
Chemistry
ISBN:9781118431221
Author:Richard M. Felder, Ronald W. Rousseau, Lisa G. Bullard
Publisher:WILEY