Organic Chemistry, 12e Study Guide/Student Solutions Manual
12th Edition
ISBN: 9781119077329
Author: T. W. Graham Solomons, Craig B. Fryhle, Scott A. Snyder
Publisher: WILEY
expand_more
expand_more
format_list_bulleted
Concept explainers
Question
Chapter 3, Problem 8PP
Interpretation Introduction
Interpretation:
Whether aniline is a stronger or a weaker base than methylamine is to be decided on the basis of fact that the
Concept introduction:
Mathematically,
The stronger the acid, the weaker the conjugate base.
The larger the
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solutionStudents have asked these similar questions
2.11 Which one of the six compounds shown below is
the strongest base?
(a) H-CEC
(c)
1
(e)
H
H
-C-C-H
H
N
(b)
I
(d) OH
(f) CI
O
P
The presence of a pi bond also makes a compound a base. With this in mind, draw the conjugate acid of ethylene, CH2=CH2.
3)
Consider the molecules of but-2-enal and but-3-enal
below. Both molecules can be deprotonated by a strong base such as lithium
diisopropylamide (LDA).
H
2
H
But-3-enal
But-2-enal
Which molecule is more acidic? Why? Use a reaction coordinate diagram(s) to
explain your answer.
Chapter 3 Solutions
Organic Chemistry, 12e Study Guide/Student Solutions Manual
Ch. 3 - Prob. 1PPCh. 3 - PRACTICE PROBLEM 3.2
Write equations showing the...Ch. 3 - PRACTICE PROBLEM 3.3 Which of the following are...Ch. 3 - Prob. 4PPCh. 3 - PRACTICE PROBLEM 3.5 Formic acid (HCO2H) has...Ch. 3 - Prob. 6PPCh. 3 - Prob. 7PPCh. 3 - Prob. 8PPCh. 3 - PRACTICE PROBLEM 3.9 Predict the outcome of the...Ch. 3 - Prob. 10PP
Ch. 3 - Prob. 11PPCh. 3 - Prob. 12PPCh. 3 - Prob. 13PPCh. 3 - Prob. 14PPCh. 3 - PRACTICE PROBLEM 3.15 Nitro groups have a large...Ch. 3 - PRACTICE PROBLEM 3.16
Your laboratory instructor...Ch. 3 - Prob. 17PPCh. 3 - Prob. 18PPCh. 3 - Prob. 19PPCh. 3 - What is the conjugate base of each of the...Ch. 3 - List the bases you gave as answers to Problem 3.20...Ch. 3 - 3.22 What is the conjugate acid of each of the...Ch. 3 - List the acids you gave as answers to Problem 3.22...Ch. 3 - Rank the following in order of increasing acidity.Ch. 3 - Without consulting tables, select the stronger...Ch. 3 - Designate the Lewis acid and Lewis base in each of...Ch. 3 - Prob. 27PCh. 3 - Prob. 28PCh. 3 - Write an equation, using the curved-arrow...Ch. 3 - 3.30 What reaction will take place if ethyl...Ch. 3 - 3.31 (a) The of formic acid. What is the? (b)...Ch. 3 - Acid HA has pKa=20; acid HB has pKa=10. (a) Which...Ch. 3 - Prob. 33PCh. 3 - 3.34 (a) Arrange the following compounds in order...Ch. 3 - 3.35 Arrange the following compounds in order of...Ch. 3 - 3.36 Arrange the following in order of increasing...Ch. 3 - Prob. 37PCh. 3 - 3.38 Supply the curved arrows necessary for the...Ch. 3 - Glycine is an amino acid that can be obtained from...Ch. 3 - 3.40 Malonic acid, , is a diprotic acid. The for...Ch. 3 - 3.41 The free-energy change, , for the ionization...Ch. 3 - 3.42 At the enthalpy change, , for the ionization...Ch. 3 - The compound at right has (for obvious reasons)...Ch. 3 - 3.44.
(a) Given the above sequence of...Ch. 3 - Prob. 45PCh. 3 - Prob. 46PCh. 3 - 3.47 As noted in Table 3.1, the of acetone, , is...Ch. 3 - Formamide (HCONH2) has a pKa of approximately 25....Ch. 3 - List all the chemical species likely to be present...Ch. 3 - Prob. 2LGPCh. 3 - Prob. 3LGPCh. 3 - Prob. 4LGP
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
- 4. The pk, of vanillin is about 9, which is much more acidic than a normal alcohol. Draw a reaction showing the deprotonation of vanillin with NaOH, and then draw six resonance structures of the conjugate base. Draw the hybrid structure and clearly indicate how the negative charge is distributed in the compound.arrow_forwardThe C-H bond in acetone, (CH3)C=O, has a pką of 19.2. Draw two resonance structures for its conjugate base. Then, explain why acetone is much more acidic than propane, CH;CH,CH3 (pKa = 50). %3Darrow_forwardно HO но он The pK, of ascorbic acid (vitamin C) is 4.17, showing that it is slightly more acidic than acetic acid (CH3CO0H, pKa 4.74). (a) Show the fou r different conjugate bases that would be formed by deprotonation of the four different OH groups in ascorbic acid. (b) Compare the stabilities of these four conjugate bases, and predict which OH group of ascorbic acid is the most acidic. (c) Compare the most stable conjugate base of ascorbic acid with the conjugate base of acetic acid, and suggest why these two compounds have similar acidities, even though ascorbic acid lacks the carboxylic acid (COOH) group.arrow_forward
- Using pKa Values to Determine Relative Acidity and Basicity Rank the following compounds in order of increasing acidity, and then rank their conjugate bases in order of increasing basicity.arrow_forward(a) Rank the following molecules from most acidic to least acidic. Use the format 1>2 if you want to indicufe lis more acidic than 2. circle the molecules which can be >50% deprotonated in water nor 요.. 애 2 ii 3 A 4arrow_forwardRank the following compounds in order of increasing acidity (1 = least acidic, 3 = most acidic) and in the space provided use resonance (of the conjugate base) to explain why the compound you have labelled “3” is the most acidic.arrow_forward
- Aniline (conjugate acid pKa 4.63) is a considerably stronger base than diphenylamine (pKa 0.79). Account for these marked differences.arrow_forward5. (a) HF is an acid. What is it's conjugate base ? (b) CIO₂ is a base. What is it's conjugate acid ? (c) What is the conjugate base of H₂PO4¹ ? (d) What is the conjugate acid of H₂PO4-¹ ?arrow_forwardIdentify the most and the least basic compound in each of the following sets. Leave the remaining answer in each set blank. a) Lithium ethoxide: b) Sodium chloride: c) Sodium acetate: Lithium diisopropylamide: Sodium formate: Sodium methoxide: Lithium acetate: Sodium acetate: Sodium phenoxide:arrow_forward
- 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 atomarrow_forwardRank the following compounds in their correct order of acidity. 1=Most acidic and 4=least acidic.arrow_forwardDO 2.8 Identify the stronger acid in each pair of compounds. (a) X H St H-C=C-H (b) O ZAarrow_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