OWLv2 with Student Solutions Manual eBook, 4 terms (24 months) Printed Access Card for McMurry's Organic Chemistry, 9th
9th Edition
ISBN: 9781305671874
Author: John E. McMurry
Publisher: Cengage Learning
expand_more
expand_more
format_list_bulleted
Concept explainers
Question
Chapter 2.SE, Problem 52AP
Interpretation Introduction
Interpretation:
Sodium bicarbonate, NaHCO3, is the sodium salt of carbonic acid (H2CO3), pKa = 6.37. Which of the substances shown in Problem 2-44 [Acetone (pKa =19.3), 2, 4-pentanedione (pKa =9.0), phenol (pKa =9.9), Acetic acid (pKa = 4.76)] will react significantly with sodium bicarbonate is to be stated.
Concept introduction:
An ion which is a weak base can deprotonate only when the substance reacting with it has a pKa value than that of its parent acid.
To determine:
Which of the substances shown in Problem 2-44 [Acetone (pKa =19.3), 2, 4-pentanedione (pKa =9.0), phenol (pKa =9.9), Acetic acid (pKa = 4.76] will react significantly with sodium bicarbonate. pKa of carbonic acid, = 6.37.
Expert Solution & Answer
Trending nowThis is a popular solution!
Students have asked these similar questions
Michael Reactions
19.52 Draw the products from the following Michael addition reactions.
1.
H&C CH
(a)
i
2. H₂O*
(b)
OEt
(c)
EtO
H₂NEt
(d)
ΕΙΟ
+
1. NaOEt
2. H₂O'
H
H
1. NaOEt
2. H₂O*
Rank the labeled protons (Ha-Hd) in order of increasing acidity, starting with the least acidic.
НОН НЬ
OHd
Онс
Can the target compound at right be efficiently synthesized in good yield from the unsubstituted benzene at left?
?
starting
material
target
If so, draw a synthesis below. If no synthesis using reagents ALEKS recognizes is possible, check the box under the drawing area.
Be sure you follow the standard ALEKS rules for submitting syntheses.
+ More...
Note for advanced students: you may assume that you are using a large excess of benzene as your starting material.
C
:0
T
Add/Remove step
G
Chapter 2 Solutions
OWLv2 with Student Solutions Manual eBook, 4 terms (24 months) Printed Access Card for McMurry's Organic Chemistry, 9th
Ch. 2.1 - Prob. 1PCh. 2.1 - Prob. 2PCh. 2.1 - Use the electronegativity values shown in Figure...Ch. 2.1 - Look at the following electrostatic potential map...Ch. 2.2 - Ethylene glycol, HOCH2CH2OH, may look nonpolar...Ch. 2.2 - Make three-dimensional drawings of the following...Ch. 2.3 - Calculate formal charges for the nonhydrogen atoms...Ch. 2.3 - Organic phosphate groups occur commonly in...Ch. 2.6 - Which of the following pairs of structures...Ch. 2.6 - Draw the indicated number of resonance forms for...
Ch. 2.7 - Nitric acid (HNO3) reacts with ammonia (NH3) to...Ch. 2.8 - Prob. 12PCh. 2.8 - Amide ion, H2N-, is a much stronger base than...Ch. 2.9 - Prob. 14PCh. 2.9 - Prob. 15PCh. 2.9 - Prob. 16PCh. 2.11 - Using curved arrows, show how the species in part...Ch. 2.11 - Prob. 18PCh. 2.12 - Of the two vitamins A and C, one is hydrophilic...Ch. 2.SE - Prob. 20VCCh. 2.SE - The following model is a representation of...Ch. 2.SE - cis-l, 2-Dichloroethylene and trans-1,...Ch. 2.SE - The following molecular models are representations...Ch. 2.SE - Predict the product(s) of the acid/base reactions...Ch. 2.SE - Use curved arrows to draw the protonated form of...Ch. 2.SE - Prob. 26MPCh. 2.SE - Double bonds can also act like Lewis bases,...Ch. 2.SE - Prob. 28APCh. 2.SE - Use the electronegativity table given in Figure...Ch. 2.SE - Which of the following molecules has a dipole...Ch. 2.SE - Prob. 31APCh. 2.SE - Phosgene, C12C=O, has a smaller dipole moment than...Ch. 2.SE - Prob. 33APCh. 2.SE - Methanethiol, CH3SH, has a substantial dipole...Ch. 2.SE - Calculate the formal charges on the atoms shown in...Ch. 2.SE - Assign formal charges to the atoms in each of the...Ch. 2.SE - Which of the following pairs of structures...Ch. 2.SE - Prob. 38APCh. 2.SE - 1, 3-Cyclobutadiene is a rectangular molecule with...Ch. 2.SE - Alcohols can act either as weak acids or as weak...Ch. 2.SE - The O-H hydrogen in acetic acid is more acidic...Ch. 2.SE - Draw electron-dot structures for the following...Ch. 2.SE - Write the products of the following acid-base...Ch. 2.SE - Rank the following substances in order of...Ch. 2.SE - Which, if any, of the substances in Problem 2-44...Ch. 2.SE - The ammonium ion (NH4+, pKa = 9.25) has a lower...Ch. 2.SE - Prob. 47APCh. 2.SE - Prob. 48APCh. 2.SE - Calculate Ka values from the following pka’s:...Ch. 2.SE - Calculate pKa values from the following Ka’s:...Ch. 2.SE - What is the pH of a 0.050 M solution of formic...Ch. 2.SE - Prob. 52APCh. 2.SE - Maleic acid has a dipole moment, but the closely...Ch. 2.SE - Assume that you have two unlabeled bottles, one of...Ch. 2.SE - Identify the acids and bases in the following...Ch. 2.SE - Which of the following pairs represent resonance...Ch. 2.SE - Draw as many resonance structures as you can for...Ch. 2.SE - Carbocations, which contain a trivalent,...Ch. 2.SE - We’ll see in the next chapter that organic...Ch. 2.SE - The azide functional group, which occurs in...Ch. 2.SE - Phenol, C6H5OH, is a stronger acid than methanol,...Ch. 2.SE - Thiamin diphosphate (TPP), a derivative of vitamin...Ch. 2.SE - Determine if each compound or ion below has a...Ch. 2.SE - Prob. 64APCh. 2.SE - Prob. 65APCh. 2.SE - Draw the conjugate base for each compound below...Ch. 2.SE - 1, 1, 1-Trichloroethanol is an acid more than 1000...
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
- The following equations represent the formation of compound MX. What is the AH for the electron affinity of X (g)? X₂ (g) → 2X (g) M (s) → M (g) M (g) M (g) + e- AH = 60 kJ/mol AH = 22 kJ/mol X (g) + e-X (g) M* (g) +X (g) → MX (s) AH = 118 kJ/mol AH = ? AH = -190 kJ/mol AH = -100 kJ/mol a) -80 kJ b) -30 kJ c) -20 kJ d) 20 kJ e) 156 kJarrow_forwardA covalent bond is the result of the a) b) c) d) e) overlap of two half-filled s orbitals overlap of a half-filled s orbital and a half-filled p orbital overlap of two half-filled p orbitals along their axes parallel overlap of two half-filled parallel p orbitals all of the abovearrow_forwardCan the target compound at right be efficiently synthesized in good yield from the unsubstituted benzene at left? starting material target If so, draw a synthesis below. If no synthesis using reagents ALEKS recognizes is possible, check the box under the drawing area. Be sure you follow the standard ALEKS rules for submitting syntheses. + More... Note for advanced students: you may assume that you are using a large excess of benzene as your starting material. C T Add/Remove step X ноarrow_forward
- Which one of the following atoms should have the largest electron affinity? a) b) c) d) 으으 e) 1s² 2s² 2p6 3s¹ 1s² 2s² 2p5 1s² 2s² 2p 3s² 3p² 1s² 2s 2p 3s² 3p6 4s2 3ds 1s² 2s² 2p6arrow_forwardAll of the following are allowed energy levels except _. a) 3f b) 1s c) 3d d) 5p e) 6sarrow_forwardA student wants to make the following product in good yield from a single transformation step, starting from benzene. Add any organic reagents the student is missing on the left-hand side of the arrow, and any addition reagents that are necessary above or below the arrow. If this product can't be made in good yield with a single transformation step, check the box below the drawing area. Note for advanced students: you may assume that an excess of benzene is used as part of the reaction conditions. : ☐ + I X This product can't be made in a single transformation step.arrow_forward
- Ppplllleeeaaasssseeee helllppp wiithhh thisss Organic chemistryyyyyy I talked like this because AI is very annoyingarrow_forwardName the family to which each organic compound belongs. The first answer has been filled in for you. compound CH₂ || CH3-C-NH2 0 ။ CH3-C-CH₂ CH=O–CH=CH, CH₂ HO CH2-CH2-CH-CH3 family amine Darrow_forward1b. Br LOHarrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
Chemistry & Chemical ReactivityChemistryISBN:9781133949640Author:John C. Kotz, Paul M. Treichel, John Townsend, David TreichelPublisher:Cengage Learning
Introduction to General, Organic and BiochemistryChemistryISBN:9781285869759Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar TorresPublisher:Cengage Learning
General, Organic, and Biological ChemistryChemistryISBN:9781285853918Author:H. Stephen StokerPublisher:Cengage Learning
Introductory Chemistry: A FoundationChemistryISBN:9781337399425Author:Steven S. Zumdahl, Donald J. DeCostePublisher:Cengage Learning
Chemistry & Chemical ReactivityChemistryISBN:9781337399074Author:John C. Kotz, Paul M. Treichel, John Townsend, David TreichelPublisher:Cengage Learning
Chemistry & Chemical Reactivity
Chemistry
ISBN:9781133949640
Author:John C. Kotz, Paul M. Treichel, John Townsend, David Treichel
Publisher:Cengage Learning
Introduction to General, Organic and Biochemistry
Chemistry
ISBN:9781285869759
Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres
Publisher:Cengage Learning
General, Organic, and Biological Chemistry
Chemistry
ISBN:9781285853918
Author:H. Stephen Stoker
Publisher:Cengage Learning
Introductory Chemistry: A Foundation
Chemistry
ISBN:9781337399425
Author:Steven S. Zumdahl, Donald J. DeCoste
Publisher:Cengage Learning
Chemistry & Chemical Reactivity
Chemistry
ISBN:9781337399074
Author:John C. Kotz, Paul M. Treichel, John Townsend, David Treichel
Publisher:Cengage Learning