ORGANIC CHEMISTRY
ORGANIC CHEMISTRY
5th Edition
ISBN: 9781259977596
Author: SMITH
Publisher: MCG
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Chapter 19, Problem 19.35P

Using the p K a table in Appendix A, determine whether each of the following bases is strong enough to deprotonate the three compounds listed below. Bases: [1] OH ; [2] CH 3 CH 2 ; [3] NH 2 ; [4] NH 3 ; [5] HC C .

a. Chapter 19, Problem 19.35P, 19.35 Using the  table in Appendix A, determine whether each of the following bases is strong enough , example  1 b. Chapter 19, Problem 19.35P, 19.35 Using the  table in Appendix A, determine whether each of the following bases is strong enough , example  2 c. Chapter 19, Problem 19.35P, 19.35 Using the  table in Appendix A, determine whether each of the following bases is strong enough , example  3

Expert Solution
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Interpretation Introduction

(a)

Interpretation: The correct pKa value for the given carboxylic acid is to be identified.

Concept introduction: Carboxylic acids are the carbon compounds that contain carboxyl group as a major functional group. They are polar due to electronegativity difference between the atoms in a compound. They sometimes exist as a dimer. Dimers are the compounds that consist of two monomer units connected by bonds or forces. Carboxylic acids are synthesized from alkynes, alkene, benzene derivatives, alcohol and allylic halides by using different reagents.

Answer to Problem 19.35P

The bases that are strong enough to deprotonate the given compounds are CH3CH2, NH2, OH, NH3 and HCC.

Explanation of Solution

The given carboxylic acid is 4-methyl benzoic acid. Its pKa value is 4.3. It is less acidic because methyl group has positive inductive effect. It donates electrons, due to which the removal of H+ ions become difficult. A base that has a higher pKa value than the pKa value of the given compound is needed to deprotonate the given compound.

The pKa value of OH, CH3CH2, NH2, NH3 and HCC is 15.74, 36, 34, 9.3 and 25 respectively.

Therefore, the bases that are strong enough to deprotonate the given compounds are CH3CH2, NH2, OH, NH3 and HCC.

Conclusion

The bases that are strong enough to deprotonate the given compounds are CH3CH2, NH2, OH, NH3 and HCC.

Expert Solution
Check Mark
Interpretation Introduction

(b)

Interpretation: The correct pKa value for the given carboxylic acid is to be identified.

Concept introduction: Carboxylic acids are the carbon compounds that contain carboxyl group as a major functional group. They are polar due to electronegativity difference between the atoms in a compound. They sometimes exist as a dimer. Dimers are the compounds that consist of two monomer units connected by bonds or forces. Carboxylic acids are synthesized from alkynes, alkene, benzene derivatives, alcohol and allylic halides by using different reagents.

Answer to Problem 19.35P

The bases that are strong enough to deprotonate the given compounds are CH3CH2, NH2, OH and HCC.

Explanation of Solution

The given compound is 4-chlorophenol. Its pKa value is 9.4. A base which has higher pKa value than 9.4 is needed to deprotonate the given compound.

The pKa value of OH, CH3CH2, NH2, NH3 and HCC is 15.74, 36, 34, 9.3 and 25 respectively.

Therefore, the bases that are strong enough to deprotonate the given compounds are CH3CH2, NH2, OH and HCC.

Conclusion

The bases that are strong enough to deprotonate the given compounds are CH3CH2, NH2, OH and HCC.

Expert Solution
Check Mark
Interpretation Introduction

(c)

Interpretation: The correct pKa value for the given carboxylic acid is to be identified.

Concept introduction: Carboxylic acids are the carbon compounds that contain carboxyl group as a major functional group. They are polar due to electronegativity difference between the atoms in a compound. They sometimes exist as a dimer. Dimers are the compounds that consist of two monomer units connected by bonds or forces. Carboxylic acids are synthesized from alkynes, alkene, benzene derivatives, alcohol and allylic halides by using different reagents.

Answer to Problem 19.35P

The bases that are strong enough to deprotonate the given compounds are CH3CH2, NH2 and HCC.

Explanation of Solution

The given carboxylic acid is 2-methyl-propan-2-ol. Its pKa value is 18. A base that has a higher pKa value than the pKa value of the given compound is needed to deprotonate the given compound.

The pKa value of OH, CH3CH2, NH2, NH3 and HCC is 15.74, 36, 34, 9.3 and 25 respectively.

Therefore, the bases that are strong enough to deprotonate the given compounds are CH3CH2, NH2 and HCC.

Conclusion

The bases that are strong enough to deprotonate the given compounds are CH3CH2, NH2 and HCC.

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Chapter 19 Solutions

ORGANIC CHEMISTRY

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