Organic Chemistry
Organic Chemistry
5th Edition
ISBN: 9780078021558
Author: Janice Gorzynski Smith Dr.
Publisher: McGraw-Hill Education
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Chapter 19, Problem 19.40P

Match the p K a values to the appropriate compound. p K a values: 0.28 , 1.24 , 2.66 , 2.86 , and 3.12 . Compounds (a) FCH 2 COOH ; (b) CF 3 COOH ; (c) F 2 CHCOOH ; (d) ICH 2 COOH ; (e) BrCH 2 COOH

Expert Solution
Check Mark
Interpretation Introduction

(a)

Interpretation: The pKa value of the given compound is to be predicted.

Concept introduction: The pKa value is inversely related to the acidic strength of the compound. The major factors that contribute to the acidic strength are s character, inductive effect and polarity. The high percentage of s character increases the acidity. There are two types of inductive effects named as positive and negative inductive effect. Positive inductive effect lowers the acidic strength of the compounds, whereas negative inductive effect increases the acidic strength of the compounds.

Answer to Problem 19.40P

The pKa value of FCH2COOH is 2.66.

Explanation of Solution

The given compound is FCH2COOH. Fluorine is electron withdrawing group due to which its acidic strength is high and pKa value is low. Only one fluorine atom is present in the compound. Therefore, the pKa value of FCH2COOH is 2.66.

Conclusion

The pKa value of FCH2COOH is 2.66.

Expert Solution
Check Mark
Interpretation Introduction

(b)

Interpretation: The pKa value of the given compound is to be predicted.

Concept introduction: The pKa value is inversely related to the acidic strength of the compound. The major factors that contribute to the acidic strength are s character, inductive effect and polarity. The high percentage of s character increases the acidity. There are two types of inductive effects named as positive and negative inductive effect. Positive inductive effect lowers the acidic strength of the compounds, whereas negative inductive effect increases the acidic strength of the compounds.

Answer to Problem 19.40P

The pKa value of CF3COOH is 0.28.

Explanation of Solution

The given compound is CF3COOH. Fluorine is highly electronegative due to which its acidic strength is high and pKa value is low.

The order of electronegativity among halogens is shown below.

I<Br<Cl<F

Three fluorine atoms are present in the compound. Therefore, the pKa value of CF3COOH is 0.28.

Conclusion

The pKa value of CF3COOH is 0.28.

Expert Solution
Check Mark
Interpretation Introduction

(c)

Interpretation: The pKa value of the given compound is to be predicted.

Concept introduction: The pKa value is inversely related to the acidic strength of the compound. The major factors that contribute to the acidic strength are s character, inductive effect and polarity. The high percentage of s character increases the acidity. There are two types of inductive effects named as positive and negative inductive effect. Positive inductive effect lowers the acidic strength of the compounds, whereas negative inductive effect increases the acidic strength of the compounds.

Answer to Problem 19.40P

The pKa value of F2CHCOOH is 1.24.

Explanation of Solution

The given compound is F2CHCOOH. Fluorine is electron withdrawing group due to which its acidic strength is high and pKa value is low.

The order of electronegativity among halogens is shown below.

I<Br<Cl<F

Two fluorine atoms are present in the compound. Therefore, the pKa value of F2CHCOOH is 1.24.

Conclusion

The pKa value of F2CHCOOH is 1.24.

Expert Solution
Check Mark
Interpretation Introduction

(d)

Interpretation: The pKa value of the given compound is to be predicted.

Concept introduction: The pKa value is inversely related to the acidic strength of the compound. The major factors that contribute to the acidic strength are s character, inductive effect and polarity. The high percentage of s character increases the acidity. There are two types of inductive effects named as positive and negative inductive effect. Positive inductive effect lowers the acidic strength of the compounds, whereas negative inductive effect increases the acidic strength of the compounds.

Answer to Problem 19.40P

The pKa value of ICH2COOH is 3.12.

Explanation of Solution

The given compound is ICH2COOH. Iodine is electron withdrawing group due to which its acidic strength is high and pKa value is low. Iodine is less electronegative as compared to fluorine.

The order of electronegativity among halogens is shown below.

I<Br<Cl<F

Only one iodine atom is present in the compound. Therefore, the pKa value of ICH2COOH is 3.12.

Conclusion

The pKa value of ICH2COOH is 3.12.

Expert Solution
Check Mark
Interpretation Introduction

(e)

Interpretation: The pKa value of the given compound is to be predicted.

Concept introduction: The pKa value is inversely related to the acidic strength of the compound. The major factors that contribute to the acidic strength are s character, inductive effect and polarity. The high percentage of s character increases the acidity. There are two types of inductive effects named as positive and negative inductive effect. Positive inductive effect lowers the acidic strength of the compounds, whereas negative inductive effect increases the acidic strength of the compounds.

Answer to Problem 19.40P

The pKa value of BrCH2COOH is 2.86.

Explanation of Solution

The given compound is BrCH2COOH. The order of electronegativity among halogens is shown below.

I<Br<Cl<F

Bromine is more electronegative as compared to iodine. Therefore, the pKa value of BrCH2COOH is 2.86.

Conclusion

The pKa value of BrCH2COOH is 2.86.

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Chapter 19 Solutions

Organic Chemistry

Ch. 19 - Problem 19.11 Identify A-D in the following...Ch. 19 - Problem 9.12 Draw the cation that results when a...Ch. 19 - Problem 19.13 Draw the products of each acid-base...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 - Problem 19.17 Rank the compounds in each group in...Ch. 19 - Problem 19.18 Rank the compounds in each group in...Ch. 19 - Prob. 19.19PCh. 19 - Problem 19.20 Which of the following pairs of...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. 19.25PCh. 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. 19.28PCh. 19 - 19.29 Give the IUPAC name for each compound. a....Ch. 19 - 19.30 Draw the structure corresponding to each...Ch. 19 - Prob. 19.31PCh. 19 - 19.32 Rank the following compounds 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 - 19.36 Draw the products of each acid-base...Ch. 19 - 19.37 Which compound in each pair has the lower ?...Ch. 19 - 19.38 Rank the compounds in each group in order of...Ch. 19 - 19.39 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 - Prob. 19.48PCh. 19 - Prob. 19.49PCh. 19 - 19.50 Draw all resonance structures of the...Ch. 19 - As we will see in Chapter 23, CH bonds are...Ch. 19 - Prob. 19.52PCh. 19 - The pKa of acetamide (CH3CONH2) is 16. Draw the...Ch. 19 - 19.54 Write out the steps needed to separate...Ch. 19 - Prob. 19.55PCh. 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 - 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 - 19.71 Hydroxy butanedioic acid occurs naturally in...Ch. 19 - 19.72 Although it was initially sold as a rat...
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