In each of the following reactions, one of the reagents contains two reactive groups (either acidic or basic). You have to decide which group will be affected under mentioned conditions. To answer this problem correctly I suggest that you use the following strategy: (i) Write the products of the reaction: conjugate acid and conjugate base. Use curved arrows to track the flow of electrons; (ii) Using Table 3.1 of the textbook estimate and write pKa values for all acidic groups you have in the reaction equation including conjugate acid; (iii) If you wrote the correct reaction the estimated pKa values should confirm that the reaction transformation changes stronger acid to weaker acid and stronger base to weaker. CH3COOHNH₂OH(1equivalent)conjugate base + conjugate acid TABLE 3.1 Relative Strength of Selected Acids and Their Conjugate BasesStrongest acidIncreasing acid strengthWeakest acidAcidHSbF6HIH₂SO4HBrHCIC6H5SO3H(CH3)2OH(CH3)2C=OHCH3OH₂H3O+HNO3CF3CO₂HHFCH3CO₂HH₂CO3CH3COCH₂COCH 3NH4+C6H5OHHCO3CH3NH3*H₂OCH3CH₂OH(CH3)3COHCH3COCH 3HC=CHH₂NH3CH₂=CH₂CH3CH3Approximate pK₂<-12-10-9-9-7-6.5-3.8-2.9-2.5-1.74-1.40.183.24.756.359.09.29.910.210.615.7161819.22535384450ConjugateBaseSbF6I™HSO4BrCIC6H5SO3(CH3)2O(CH3)2C=OCH3OHH₂ONO3CF3CO2F™CH3CO₂HCO3CH3COCHCOCH 3NH3C6H₂O™CO3²-CH3NH2OHCH3CH₂O™(CH3)3COCH₂COCH 3HC=CH-NH₂™CH₂=CH-CH3CH₂Weakest baseIncreasing base strengthStrongest base

Basic about acidity and basicity

Answered: In each of the following reactions, one…

Chemistry

10th Edition

ISBN:9781305957404

Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Chapter1: Chemical Foundations

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Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...

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In each of the following reactions, one of the reagents contains two reactive groups (either acidic or basic). You have to decide which group will be affected under mentioned conditions. To answer this problem correctly I suggest that you use the following strategy: (i) Write the products of the reaction: conjugate acid and conjugate base. Use curved arrows to track the flow of electrons; (ii) Using Table 3.1 of the textbook estimate and write pKa values for all acidic groups you have in the reaction equation including conjugate acid; (iii) If you wrote the correct reaction the estimated pKa values should confirm that the reaction transformation changes stronger acid to weaker acid and stronger base to weaker.

CH3COOH
NH₂
OH
(1equivalent)
conjugate base + conjugate acid

TABLE 3.1 Relative Strength of Selected Acids and Their Conjugate Bases
Strongest acid
Increasing acid strength
Weakest acid
Acid
HSbF6
HI
H₂SO4
HBr
HCI
C6H5SO3H
(CH3)2OH
(CH3)2C=OH
CH3OH₂
H3O+
HNO3
CF3CO₂H
HF
CH3CO₂H
H₂CO3
CH3COCH₂COCH 3
NH4+
C6H5OH
HCO3
CH3NH3*
H₂O
CH3CH₂OH
(CH3)3COH
CH3COCH 3
HC=CH
H₂
NH3
CH₂=CH₂
CH3CH3
Approximate pK₂
<-12
-10
-9
-9
-7
-6.5
-3.8
-2.9
-2.5
-1.74
-1.4
0.18
3.2
4.75
6.35
9.0
9.2
9.9
10.2
10.6
15.7
16
18
19.2
25
35
38
44
50
Conjugate
Base
SbF6
I™
HSO4
Br
CI
C6H5SO3
(CH3)2O
(CH3)2C=O
CH3OH
H₂O
NO3
CF3CO2
F™
CH3CO₂
HCO3
CH3COCHCOCH 3
NH3
C6H₂O™
CO3²-
CH3NH2
OH
CH3CH₂O™
(CH3)3CO
CH₂COCH 3
HC=C
H-
NH₂™
CH₂=CH-
CH3CH₂
Weakest base
Increasing base strength
Strongest base

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