Essential Organic Chemistry (3rd Edition)
3rd Edition
ISBN: 9780321937711
Author: Paula Yurkanis Bruice
Publisher: PEARSON
expand_more
expand_more
format_list_bulleted
Concept explainers
Textbook Question
Chapter 2, Problem 41P
- a. List the following carboxylic acids in order from strongest acid to weakest acid:
- b. How does the presence of an electronegative substituent such as Cl affect the acidity of a carboxylic acid?
- c. How does the location of the substituent affect the acidity of the carboxylic acid?
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solutionStudents have asked these similar questions
A carboxylic acid has two oxygen atoms, each with two nonbonding pairs of electrons. (b) Compare the resonance forms with those given previously for an acid protonated on thecarbonyl oxygen atom.(c) Explain why the carbonyl oxygen atom of a carboxylic acid is more basic than thehydroxy oxygen.
A carboxylic acid has two oxygen atoms, each with two nonbonding pairs of electrons.(a) Draw the resonance forms of a carboxylic acid that is protonated on the hydroxyoxygen atom.(b) Compare the resonance forms with those given previously for an acid protonated on thecarbonyl oxygen atom
78) Why are primary alcohols more acidic than tertiary alcohols, in general?
Because tertiary alcohols have less acidic hydrogens.
Because primary alcohols have less electron-donating groups which create more effective charge separation between oxygen and hydrogen atom, making it more acidic.
Because primary alcohols are more polar than tertiary alcohols.
Because primary alcohols have less electron-donating groups which decrease electron density on oxygen, making it more susceptible for H+ to depart from the structure.
Chapter 2 Solutions
Essential Organic Chemistry (3rd Edition)
Ch. 2.1 - Which of the following are not acids? CH3COOH CO2...Ch. 2.1 - Draw the products of the acidbase reaction when a....Ch. 2.1 - a.What is the conjugate acid of each of the...Ch. 2.2 - a. Which is a stronger acid, one with a pKa of 5.2...Ch. 2.2 - Prob. 5PCh. 2.2 - Antacids are compounds that neutralize stomach...Ch. 2.2 - Are the following body fluids acidic or basic? a....Ch. 2.3 - Draw the conjugate acid of each of the following:...Ch. 2.3 - a. Write an equation showing CH3OH reacting as an...Ch. 2.3 - Prob. 10P
Ch. 2.3 - a. Which is a stronger base, CH3COO or HCOO? (The...Ch. 2.3 - Using the pKa values in Section 2.3, rank the...Ch. 2.4 - Prob. 13PCh. 2.5 - Prob. 14PCh. 2.5 - Ethyne has a pKa value of 25, water has a pKa...Ch. 2.5 - Which of the following bases can remove a proton...Ch. 2.6 - List the ions (CH3, NH2, HO, and F) in order from...Ch. 2.6 - List the carbanions shown in the margin in order...Ch. 2.6 - Which is a stronger acid?Ch. 2.6 - a. Draw the products of the following reactions: A...Ch. 2.6 - List the halide ions (F, Cl, Br, and I) in order...Ch. 2.6 - a. Which is more electronegative, oxygen or...Ch. 2.6 - Which is a stronger acid? a. HCl or HBr b....Ch. 2.6 - a. Which of the halide ions (F, Cl, Br, and I) is...Ch. 2.6 - Which is a stronger base? a. H2O or HO b. H2O or...Ch. 2.7 - Which is a stronger acid? a. CH3OCH2CH2OH or...Ch. 2.7 - Which is a stronger base?Ch. 2.8 - Fosamax has six acidic groups. The structure of...Ch. 2.8 - Which is a stronger acid? Why?Ch. 2.10 - For each of the following compounds (shown in...Ch. 2.10 - Prob. 33PCh. 2.11 - Write the equation that shows how a buffer made by...Ch. 2.11 - What products are formed when each of the...Ch. 2 - a. List the following alcohols in order from...Ch. 2 - Which is a stronger base? a. HS or HO b. CH3O or...Ch. 2 - Prob. 40PCh. 2 - a. List the following carboxylic acids in order...Ch. 2 - For the following compound, a. draw its conjugate...Ch. 2 - List the following compounds in order from...Ch. 2 - For each of the following compounds, draw the form...Ch. 2 - Give the products of the following acidbase...Ch. 2 - Prob. 46PCh. 2 - For each compound, indicate the atom that is most...Ch. 2 - Tenormin, a member of the group of drugs known as...Ch. 2 - From which acids can HO remove a proton in a...Ch. 2 - Prob. 50PCh. 2 - Which is a stronger acid? a. CH29CHCOOH or...Ch. 2 - Prob. 52PCh. 2 - Prob. 53PCh. 2 - How could you separate a mixture of the following...Ch. 2 - Prob. 1PCh. 2 - Prob. 2PCh. 2 - Draw the products of the following acidbase...Ch. 2 - Prob. 4PCh. 2 - Prob. 5PCh. 2 - Prob. 6PCh. 2 - Prob. 7PCh. 2 - Prob. 8PCh. 2 - Prob. 9PCh. 2 - Prob. 10PCh. 2 - Prob. 11PCh. 2 - Prob. 12PCh. 2 - Prob. 13PCh. 2 - Prob. 14P
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
- Amino acids such as glycine are the building blocks of large molecules called proteins that give structure to muscle, tendon, hair, and nails. a. Explain why glycine does not actually exist in the form with all atoms uncharged, but actually exists as a salt called a zwitterion. b. What product is formed when glycine is treated with concentrated HCl? c. What product is formed when glycine is treated with NaOH?arrow_forwardAmino acids such as glycine are the building blocks of large molecule.called proteins that give structure to muscle, tendon, hair, and nails.a.Explain why glycine does not actually exist in the form with all atoms uncharged, but actually exists as a salt called a zwitterion. b.What product is formed when glycine is treated with concentrated HCl? c. What product is formed when glycine is treated with NaOH?arrow_forwardorganic chemistry 30) Which compound is the strongest acid?arrow_forward
- Ketones 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_forwardReaction with Strong Acids Table 9.8 Observations on the reaction of aniline with strong acids. Sample Observations +/- Aniline + H2SO4 Aniline + HCl Explain, in 1 – 3 sentences, the difference in the reaction of aniline with H2SO4 and HCl. ___________________________________________________________________________ ___________________________________________________________________________ ___________________________________________________________________________ Reactions: Aniline + H2SO4 Aniline + HClarrow_forwardIf the base was changed from NaH to LDA, the major product changes(shown below). Think critically about the change in base, why is this change in major products observed? (1—3 sentences)arrow_forward
- If compound A has a ka of 3.0 x 10-11 , compound B has a ka of 1.1 x 10-10 and compound C has a ka of 1.8 x 10-5, which compound is the weakest acid?arrow_forwardIs p-methylphenol more acidic than phenol? Why or why not?arrow_forward1. The nitroprusside test is used to detect methyl ketones. What reagents are used in the Nitroprusside test?a. What is the color of the positive result?b. What is the color of the negative result?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
General Chemistry | Acids & Bases; Author: Ninja Nerd;https://www.youtube.com/watch?v=AOr_5tbgfQ0;License: Standard YouTube License, CC-BY