Organic Chemistry: Principles and Mechanisms (Second Edition)
2nd Edition
ISBN: 9780393663556
Author: Joel Karty
Publisher: W. W. Norton & Company
expand_more
expand_more
format_list_bulleted
Concept explainers
Question
Chapter 6, Problem 6.18YT
Interpretation Introduction
Interpretation:
The difference in pKa between the protonated and uncharged
Concept introduction:
Generally, the charged species is significantly higher in energy and thus less stable than its uncharged species. A proton is significantly more acidic when the atom to which it is attached is positively charged than when that atom is uncharged. The pKa value of charged species is less as compared to uncharged species. The less pKa value means more acidic species.
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solutionStudents have asked these similar questions
[References]
Answer questions a-c about the Bronsted acid-base reaction below using the identifying letters A-D below each structure. The pKa's for the acids of interest are: acetic acid (pK,
4.8), and hydrogen bromide (pK,=-9).
CH3
Br
CH3
H-Br
OH
B
acetic acid
bromide
acetate
hydrogen bromide
a) The stronger base is
b) Its conjugate acid is
c) The species that predominate at equilibrium are (two letters, e.g. ac)
Submit Answer
Try Another Version
1 item attempt remaining
Visited
Previous
Nex
Email Instructor
Sav
Cengage Learning | Cengage Technical Support
Answer questions a-c about the Bronsted acid-base reaction below using the Q41
identifying letters A-D below each structure.
A table of pk, values for various organic and inorganic acids can be found in the
references section.
NH₂
A
amide
B
ethyl acetate
CH₂
NH3
C
ammonial
+
I
CH₂
D
ethyl acetate
enolate
a) The weaker acid is
b) Its conjugate base is
c) The species that predominate at equilibrium are (two letters, e.g. AC)
8. Draw the structures of the conjugate acid and base for the following reaction. Provide
the mechanism for their formation using curved arrows.
pK
-17
-35
conjugate acid
conjugate base
Chapter 6 Solutions
Organic Chemistry: Principles and Mechanisms (Second Edition)
Ch. 6 - Prob. 6.1PCh. 6 - Prob. 6.2PCh. 6 - Prob. 6.3PCh. 6 - Prob. 6.4PCh. 6 - Prob. 6.5PCh. 6 - Prob. 6.6PCh. 6 - Prob. 6.7PCh. 6 - Prob. 6.8PCh. 6 - Prob. 6.9PCh. 6 - Prob. 6.10P
Ch. 6 - Prob. 6.11PCh. 6 - Prob. 6.12PCh. 6 - Prob. 6.13PCh. 6 - Prob. 6.14PCh. 6 - Prob. 6.15PCh. 6 - Prob. 6.16PCh. 6 - Prob. 6.17PCh. 6 - Prob. 6.18PCh. 6 - Prob. 6.19PCh. 6 - Prob. 6.20PCh. 6 - Prob. 6.21PCh. 6 - Prob. 6.22PCh. 6 - Prob. 6.23PCh. 6 - Prob. 6.24PCh. 6 - Prob. 6.25PCh. 6 - Prob. 6.26PCh. 6 - Prob. 6.27PCh. 6 - Prob. 6.28PCh. 6 - Prob. 6.29PCh. 6 - Prob. 6.30PCh. 6 - Prob. 6.31PCh. 6 - Prob. 6.32PCh. 6 - Prob. 6.33PCh. 6 - Prob. 6.34PCh. 6 - Prob. 6.35PCh. 6 - Prob. 6.36PCh. 6 - Prob. 6.37PCh. 6 - Prob. 6.38PCh. 6 - Prob. 6.39PCh. 6 - Prob. 6.40PCh. 6 - Prob. 6.41PCh. 6 - Prob. 6.42PCh. 6 - Prob. 6.43PCh. 6 - Prob. 6.44PCh. 6 - Prob. 6.45PCh. 6 - Prob. 6.46PCh. 6 - Prob. 6.47PCh. 6 - Prob. 6.48PCh. 6 - Prob. 6.49PCh. 6 - Prob. 6.50PCh. 6 - Prob. 6.51PCh. 6 - Prob. 6.52PCh. 6 - Prob. 6.53PCh. 6 - Prob. 6.54PCh. 6 - Prob. 6.55PCh. 6 - Prob. 6.56PCh. 6 - Prob. 6.57PCh. 6 - Prob. 6.58PCh. 6 - Prob. 6.59PCh. 6 - Prob. 6.60PCh. 6 - Prob. 6.61PCh. 6 - Prob. 6.62PCh. 6 - Prob. 6.63PCh. 6 - Prob. 6.64PCh. 6 - Prob. 6.65PCh. 6 - Prob. 6.66PCh. 6 - Prob. 6.67PCh. 6 - Prob. 6.68PCh. 6 - Prob. 6.69PCh. 6 - Prob. 6.70PCh. 6 - Prob. 6.71PCh. 6 - Prob. 6.72PCh. 6 - Prob. 6.73PCh. 6 - Prob. 6.74PCh. 6 - Prob. 6.75PCh. 6 - Prob. 6.76PCh. 6 - Prob. 6.77PCh. 6 - Prob. 6.78PCh. 6 - Prob. 6.79PCh. 6 - Prob. 6.80PCh. 6 - Prob. 6.81PCh. 6 - Prob. 6.82PCh. 6 - Prob. 6.83PCh. 6 - Prob. 6.84PCh. 6 - Prob. 6.85PCh. 6 - Prob. 6.86PCh. 6 - Prob. 6.87PCh. 6 - Prob. 6.88PCh. 6 - Prob. 6.1YTCh. 6 - Prob. 6.2YTCh. 6 - Prob. 6.3YTCh. 6 - Prob. 6.4YTCh. 6 - Prob. 6.5YTCh. 6 - Prob. 6.6YTCh. 6 - Prob. 6.7YTCh. 6 - Prob. 6.8YTCh. 6 - Prob. 6.9YTCh. 6 - Prob. 6.10YTCh. 6 - Prob. 6.11YTCh. 6 - Prob. 6.12YTCh. 6 - Prob. 6.13YTCh. 6 - Prob. 6.14YTCh. 6 - Prob. 6.15YTCh. 6 - Prob. 6.16YTCh. 6 - Prob. 6.17YTCh. 6 - Prob. 6.18YTCh. 6 - Prob. 6.19YTCh. 6 - Prob. 6.20YT
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
- 1) Consider the reaction AH+ H₂O A:+H3O¹. For the following named acids: 1) draw the structure of the acid, 2) give the approximate pKa value of the acid in multiples of 5, 3) give the name of the conjugate base, and 4) draw the structure of the conjugate base. m-Chlorophenol 3-Pentanone acid Conj. base acid Conj. base pKa Benzoic acid pka_ iso-Butyl ammonium ion pka_ Diethyl Malonate pka_ Benzyl oxonium ion pka_ 1-pentyne pKa pKa Ethyl Acetate pKaarrow_forward14. Rank the indicated protons in order of decreasing acidity. HOT TeH 2 IZ 3 SeH-5arrow_forwardWhich of the following statements are TRUE for molecule below? i iv H2N, но. NH i H2N NH General pKa values: Protonated amines (with a positive charge): 9-11 Alcohols: 15-17 Carboxylic acids: 3-5 O This molecule will have a net charge of 0 at pH=7 O This molecule will have a net charge of +1 at pH=7 This molecule will have a net charge of +2 at pH=2 i is more basic than ii due to resonance O iv is more acidic than v due to resonancearrow_forward
- Rank the following molecules according their acidity. (1 = lowest pka) OEt O 요 ii iiNet il 요 NEt₂ O O CF 3 Predict how the highest pka from question 9 compares with the lowest pka from question 8.arrow_forwardUsing the pk, table, estimate pk, values for the most acidic group on the compounds below, and draw the structure of the conjugate base that results when this group donates a proton. Use the pka table above and/or from the Reference Tables. a) b) O. O H OH O O -NH₂ -NH₂ Answer a. The most acidic group is the protonated amine, pka ~ 5-9 b. Alpha proton by the C=O group, pka ~ 18-20 c. Thiol, pka 10 d. Carboxylic acid, pka ~ 5 e. Carboxylic acid, pka ~ 5 c) OH H₂N SH NH₂ OH asparagine H lysergic acid. OH N H CH3 Can someone please explain these answers. Including which protons being compared on the compound.arrow_forwardAnswer questions a-c about the Bronsted acid-base reaction below using the identifying letters A-D below each structure. A table of pK, values for various organic and inorganic acids can be found in the references section. CH3- CH3 но HO HO. OH acetic acid bicarbonate acetate carbonic acid a) The weaker base is b) Its conjugate acid is c) The species that predominate at equilibrium are (two letters, e.g. AC)arrow_forward
- 2. Show the structures of the missing substance(s) in each of the following acid-base equilibria. Write your answers in the blank space of the missing substance(s). Example: CH,-CH,-NH, CH;-CH,–NH, + H,0 = + OH (ANSWER) -NH, + H,O = -NH, а. (ANSWER) + H,0 = CH;-CH–NH,-CH, + OH b. (ANSWER) Diethylamine + H0= C. (ANSWER) (ANSWER)arrow_forward10. Rank the following in order of acidity of their -OH group (1-4: 1 for strongest) Explain the reasoning for your answr. Do not say" because of their pKa values!" You need to use ARIO and solvation to explain the reason underlying their relative_pKa values 10.a он OH он он CI 10b. ОН ОН OH OHarrow_forwardA ka of weak acid is 1 E-6, this means that For 1 million unionized acid, there is just one molecule is ionized .a O The concentration of hydronium ion equals the square root of its pKa value .b O For 1 million ionized acid, there is just one molecule is unionized .c O The concentration of hydroxyl ion equals the square root of its pka value .d Oarrow_forward
- 12. While each molecule below has more protons (H-atoms) than being shown, just focus on the protons identified. Compare the two protons identified. 1) Draw the two conjugate bases that could possibly result (althou gh one will be preferred over the other). The purpose here is to make you look at the conjugate base and the atom upon which the negative charge resides, then you should consider your SERIO factors. 2) Identify which proton is more acidic by circling the H, or H, on the original molecule. 3) Explain why by comparing the conjugate bases. Cirele the factor you considered when comparing the stabilities of the conjugate bases. Explanation: Size Electronegativity Resonance Inductive effect Orbital hybridization СвА св, Explanation: Size Electronegativity Resonance Inductive effect Orbital hybridization св, св,arrow_forwardUsing only the information in the pK, table below, write an estimated pK, value for each labeled H in the two structures below. For example, if the pK, value of the H labeled a has an estimated value of 50, write 50 in the first box of the answer table and so on. acid pK, H pKa a CH4 50 H a : NH3 35 d HC=CH 25 19 CH,CH3 H H,0 16 15 CH,CNH, + NH. 9. 5 CH,COH H,0* - 2arrow_forward6) Assign a given pka to the following compounds. CF3 F₂C OH → он NH₂ H₂Se CF₂ 7) In class we talked about the concept of pKH, which is the pK₂ of the protonated version of the noted molecule. Assign a given pkan to the following molecules. Two of the molecules are so similar it would hard to predict their relative pKan values from structure alone. 9) Circle the most acidic species below. OH NH₂ 8] Circle the weakest base from along the compounds below. H₂S ново F₂C OH O NH pk₂ 5.4 9.3 12.9 15.9 H₂O РКан -10 9.2 10.7 10.8arrow_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