ORGANIC CHEMISTRY-PACKAGE >CUSTOM<
10th Edition
ISBN: 9781260028355
Author: Carey
Publisher: MCG CUSTOM
expand_more
expand_more
format_list_bulleted
Concept explainers
Videos
Question
Chapter 1.13, Problem 36P
Interpretation Introduction
Interpretation:
It is to be shown that the two shown compounds form the same conjugate base on ionization. The atom in the conjugate base, which bears the greater share of negative charge, is to be determined.
Concept introduction:
Acids, upon ionization, form the corresponding conjugate base.
During ionization, the acidic proton is lost, and the conjugate base bears a negative charge on the atom to which the proton was attached.
This negative charge can be delocalized in the conjugate base, resulting in one or more resonance structures.
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solution
Students have asked these similar questions
Identify the most acidic compound between the following moleculesDraw the resonance structures of the conjugate base of the acid chosen in (a). Use the curved arrows to show the movement of electrons and the resonance arrows to show the relationship between these structures. All lone electron pairs and charges must be clearly indicated
Arrange the numbered protons in decreasing order of acidity, explain the reasoning based upon the conjugate bases.
Provide the bond line structures of two acids, one whose conjugate base is resonance stabilized and one which is not. Explain the effect that resonance will have on acidity.
Chapter 1 Solutions
ORGANIC CHEMISTRY-PACKAGE >CUSTOM<
Ch. 1.1 - How many electrons does carbon have? How many are...Ch. 1.1 - Referring to the periodic table as needed, write...Ch. 1.2 - Species that have the same number of electrons are...Ch. 1.2 - Which of the following ions possess a noble gas...Ch. 1.2 - Prob. 5PCh. 1.3 - Prob. 6PCh. 1.3 - Problem 1.7 All of the hydrogens are bonded to...Ch. 1.4 - Problem 1.8 In which of the compounds...Ch. 1.4 - Indicate the direction of the dipole for the...Ch. 1.5 - Prob. 10P
Ch. 1.5 - The following inorganic species will be...Ch. 1.5 - Prob. 12PCh. 1.6 - Prob. 13PCh. 1.6 - Problem 1.14 Nitrosomethane and formaldoxime both...Ch. 1.6 - Prob. 15PCh. 1.7 - All of the bonds in the carbonate ion (CO32-) are...Ch. 1.7 - Prob. 17PCh. 1.8 - Prob. 18PCh. 1.8 - Prob. 19PCh. 1.9 - Sodium borohydride, NaBH4, has an ionic bond...Ch. 1.9 - Prob. 21PCh. 1.10 - Which of the following compounds would you expect...Ch. 1.11 - Using the curved arrow to guide your reasoning,...Ch. 1.11 - Prob. 24PCh. 1.11 - Prob. 25PCh. 1.12 - Prob. 26PCh. 1.12 - Prob. 27PCh. 1.12 - Prob. 28PCh. 1.12 - Prob. 29PCh. 1.12 - Prob. 30PCh. 1.13 - Which is the stronger acid, H2O or H2S? Which is...Ch. 1.13 - Prob. 32PCh. 1.13 - Prob. 33PCh. 1.13 - Hypochlorous and hypobromous acid (HOClandHOBr)...Ch. 1.13 - Prob. 35PCh. 1.13 - Prob. 36PCh. 1.14 - What is the equilibrium constant for the following...Ch. 1.14 - Prob. 38PCh. 1.14 - Prob. 39PCh. 1.15 - Write an equation for the Lewis acid/Lewis base...Ch. 1 - Write a Lewis formula for each of the following...Ch. 1 - Prob. 42PCh. 1 - Write structural formulas for all the...Ch. 1 - Prob. 44PCh. 1 - Expand the following structural representations so...Ch. 1 - Each of the following species will be encountered...Ch. 1 - Consider Lewis formulas A, B, and C: H2 C -NN:...Ch. 1 - Prob. 48PCh. 1 - Prob. 49PCh. 1 - Prob. 50PCh. 1 - Prob. 51PCh. 1 - Prob. 52PCh. 1 - Prob. 53PCh. 1 - Prob. 54PCh. 1 - Which compound in each of the following pairs...Ch. 1 - With a pKa of 11.6, hydrogen peroxide is a...Ch. 1 - The structure of montelukast, an antiasthma drug,...Ch. 1 - One acid has a pKa of 2, the other has a pKa of 8....Ch. 1 - Calculate Ka for each of the following acids,...Ch. 1 - Rank the following in order of decreasing acidity....Ch. 1 - Rank the following in order of decreasing...Ch. 1 - Consider 1.0 M aqueous solutions of each of the...Ch. 1 - Prob. 63PCh. 1 - Prob. 64PCh. 1 - Prob. 65PCh. 1 - Prob. 66PCh. 1 - Prob. 67PCh. 1 - Prob. 68PCh. 1 - Amide Lewis Structural Formulas Lewis formulas are...Ch. 1 - Amide Lewis Structural Formulas Lewis formulas are...Ch. 1 - Amide Lewis Structural Formulas Lewis formulas are...Ch. 1 - Prob. 72DSPCh. 1 - Amide Lewis Structural Formulas Lewis formulas are...Ch. 1 - Amide Lewis Structural Formulas Lewis formulas are...
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
- Complete the equation for the reaction between each Lewis acid-base pair. In each equation, label which starting material is the Lewis acid and which is the Lewis base; use curved arrows to show the flow of electrons in each reaction. In doing this problem, it is essential that you show valence electrons for all atoms participating in each reaction. (a) (b) (c) (d)arrow_forwardThe following are equivalent ways of asking about the acidity of an H atom: • What is the most acidic H on the molecule? • Which H is associated with the published pKa value? • Which H on the molecule is easiest to remove? • Which H on the molecule takes the least energy to remove? • Which bond to an H is most polarized? • For which H atom is removal least uphill in energy? • Which bond to an H atom, when broken, results in the lowest PE conjugate base? We will often find the last of these questions is easiest to answer. To do this, find all the different Hatoms on the molecule, and draw all possible conjugate bases.Only the lowest-energy one is the “real” conjugate base. Identify this structure, and you have found the most acidic H. Use this strategy to find the most acidic H on each of the following molecules. Note: Each structure hasat least three different kinds of H’s, so draw at least three unique conjugate bases for each.arrow_forwardFor the following compounds, write the conjugate base that would result if the labeled proton were removed. Include resonance structures if there are any. Indicate which of the two labeled protons you expect to be more acidic and why.arrow_forward
- Predict which of the following compounds is more acidic. Fill in the blanks. In the conjugate base of the first compound, resonance delocalizes the neagtive charge over two nitrogen atoms and two carbon atoms, while the conjugate base of the second compound has a negative charge deloclized by resonance over one nitrogen atom and three carbon atoms. Since nitrogen is _______ (more or less) electronegative than carbon, nitrogen is ________ (more or less) capable of stabilizing a negative charge. Therefore, the conjugate base of the ______ (first or second) compound is more stable than the conjugate base of the ________ (first or second) compound. As a result, the ________ (first or second) compound will be more acidic.arrow_forwardFor the molecules below, draw the acid dissociation reaction. If a conjugate base has resonance structures, draw them all. Then, identify the stronger acid in each of the pairs shown below and provide an explanation for each.arrow_forwardCompare the basisity of t-BuOK and KHMDS. Which is a stronger base and why?arrow_forward
- Arrange the following compounds based on their increasing acidity. Write 1 for weakest acid, 2 for the next, then 3, then 4 and 5 for strongest acid,arrow_forwarda. Which of the acids in the table above has the strongest conjugate base? b. What is the structure of the strongest acid in the table above?arrow_forwardDraw the conjugate base resulting from removal of proton A, proton B, or proton C. If the lone pair generated by deprotonation delocalizes by resonance, draw another resonance structure that results from delocalization of that lone pair. Include lone pairs and non-zero formal charge.arrow_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
Principles of Modern ChemistryChemistryISBN:9781305079113Author:David W. Oxtoby, H. Pat Gillis, Laurie J. ButlerPublisher:Cengage Learning
Organic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage Learning
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning
Principles of Modern Chemistry
Chemistry
ISBN:9781305079113
Author:David W. Oxtoby, H. Pat Gillis, Laurie J. Butler
Publisher:Cengage Learning
Organic Chemistry: A Guided Inquiry
Chemistry
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Cengage Learning
General Chemistry | Acids & Bases; Author: Ninja Nerd;https://www.youtube.com/watch?v=AOr_5tbgfQ0;License: Standard YouTube License, CC-BY