Organic Chemistry-Package(Custom)
Organic Chemistry-Package(Custom)
4th Edition
ISBN: 9781259141089
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-Package(Custom)

Ch. 19 - Prob. 19.11PCh. 19 - Draw the products of each acid-base reaction.Ch. 19 - Problem 19.14 Given the values in Appendix A,...Ch. 19 - Problem 19.15 Rank the labeled protons in...Ch. 19 - Problem 19.16 Match each of the following values ...Ch. 19 - Rank the compounds in each group in order of...Ch. 19 - Rank the compounds in each group in order of...Ch. 19 - Prob. 19.18PCh. 19 - Which of the following pairs of compounds can be...Ch. 19 - Problem 19.21 Two other commonly used sulfonic...Ch. 19 - Problem 19.22 Draw both enantiomers of each amino...Ch. 19 - Problem 19.23 Explain why amino acids, unlike most...Ch. 19 - Problem 19.24 Draw the positively charged,...Ch. 19 - Prob. 19.24PCh. 19 - Problem 19.26 Explain why the of the group of...Ch. 19 - Answer each question for A and B depicted in the...Ch. 19 - Prob. 19.27PCh. 19 - Give the IUPAC name for each compound. a....Ch. 19 - Prob. 19.29PCh. 19 - Draw the structures and give the IUPAC names for...Ch. 19 - Prob. 19.31PCh. 19 - Rank the compounds in each group in order of...Ch. 19 - 19.33 Draw the organic products formed in each...Ch. 19 - 19.34 Identify the lettered compounds in each...Ch. 19 - 19.35 Using the table in Appendix A, determine...Ch. 19 - Draw the products of each acid-base reaction, and...Ch. 19 - Which compound in each pair has the lower pKa?...Ch. 19 - 19.38 Rank the compounds in each group in order of...Ch. 19 - Rank the compounds in each group in order of...Ch. 19 - 19.40 Match the values to the appropriate...Ch. 19 - Prob. 19.41PCh. 19 - 19.42 Which carboxylic acid has the lower ,...Ch. 19 - Prob. 19.43PCh. 19 - 19.44 Explain the following statement. Although...Ch. 19 - Prob. 19.45PCh. 19 - 19.46 Explain why the of compound A is lower than...Ch. 19 - 19.47 Rank the following compounds in order of...Ch. 19 - Explain the following result. Acetic acid...Ch. 19 - 19.50 Draw all resonance structures of the...Ch. 19 - As we will see in Chapter 23, CH bonds are...Ch. 19 - Prob. 19.51PCh. 19 - The pKa of acetamide (CH3CONH2) is 16. Draw the...Ch. 19 - 19.54 Write out the steps needed to separate...Ch. 19 - Prob. 19.54PCh. 19 - Can octane and octan -1- ol be separated using an...Ch. 19 - 19.57 Identify each compound from its spectral...Ch. 19 - 19.58 Use the NMR and IR spectra given below to...Ch. 19 - 19.59 An unknown compound (molecular formula )...Ch. 19 - 19.60 Propose a structure for (molecular formula...Ch. 19 - Prob. 19.60PCh. 19 - 19.61 Match the data to the appropriate...Ch. 19 - Prob. 19.62PCh. 19 - Prob. 19.63PCh. 19 - Prob. 19.64PCh. 19 - 19.65 For each amino acid ,draw its neutral,...Ch. 19 - Calculate the isoelectric point for each amino...Ch. 19 - 19.67 Lysine and tryptophan are two amino acids...Ch. 19 - Prob. 19.68PCh. 19 - Prob. 19.69PCh. 19 - Prob. 19.70PCh. 19 - Prob. 19.71PCh. 19 - 19.71 Hydroxy butanedioic acid occurs naturally in...Ch. 19 - 19.72 Although it was initially sold as a rat...
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