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

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