It is to be determined in which of the four molecules A-D the pKa value of the OH proton is expected to be most similar to that of cyclohexanol. Concept introduction: The acidity of a proton depends primarily on the functional group to which it belongs. Nearby structural features can modify the acidity. A highly electronegative atom such as fluorine or oxygen on an adjacent carbon can significantly change the pKa. Another feature than can modify the acidity of a proton is a double bond on the carbon to which the proton is attached. Both features increase the acidity of the proton, reducing its pKa value.

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Answer 1

Question

Chapter 6, Problem 6.52P

Interpretation Introduction

Interpretation:

It is to be determined in which of the four molecules A-D the pKa value of the OH proton is expected to be most similar to that of cyclohexanol.

Concept introduction:

The acidity of a proton depends primarily on the functional group to which it belongs. Nearby structural features can modify the acidity. A highly electronegative atom such as fluorine or oxygen on an adjacent carbon can significantly change the pKa. Another feature than can modify the acidity of a proton is a double bond on the carbon to which the proton is attached. Both features increase the acidity of the proton, reducing its pKa value.

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Answer 2

Question

Chapter 6, Problem 6.52P

Interpretation Introduction

Interpretation:

It is to be determined in which of the four molecules A-D the pKa value of the OH proton is expected to be most similar to that of cyclohexanol.

Concept introduction:

The acidity of a proton depends primarily on the functional group to which it belongs. Nearby structural features can modify the acidity. A highly electronegative atom such as fluorine or oxygen on an adjacent carbon can significantly change the pKa. Another feature than can modify the acidity of a proton is a double bond on the carbon to which the proton is attached. Both features increase the acidity of the proton, reducing its pKa value.

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Answer 3

Question

Chapter 6, Problem 6.52P

Interpretation Introduction

Interpretation:

It is to be determined in which of the four molecules A-D the pKa value of the OH proton is expected to be most similar to that of cyclohexanol.

Concept introduction:

The acidity of a proton depends primarily on the functional group to which it belongs. Nearby structural features can modify the acidity. A highly electronegative atom such as fluorine or oxygen on an adjacent carbon can significantly change the pKa. Another feature than can modify the acidity of a proton is a double bond on the carbon to which the proton is attached. Both features increase the acidity of the proton, reducing its pKa value.

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Answer 4

Question

Chapter 6, Problem 6.52P

Interpretation Introduction

Interpretation:

It is to be determined in which of the four molecules A-D the pKa value of the OH proton is expected to be most similar to that of cyclohexanol.

Concept introduction:

The acidity of a proton depends primarily on the functional group to which it belongs. Nearby structural features can modify the acidity. A highly electronegative atom such as fluorine or oxygen on an adjacent carbon can significantly change the pKa. Another feature than can modify the acidity of a proton is a double bond on the carbon to which the proton is attached. Both features increase the acidity of the proton, reducing its pKa value.

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Answer 5

Chapter 6, Problem 6.52P

Interpretation Introduction

Interpretation:

It is to be determined in which of the four molecules A-D the pKa value of the OH proton is expected to be most similar to that of cyclohexanol.

Concept introduction:

The acidity of a proton depends primarily on the functional group to which it belongs. Nearby structural features can modify the acidity. A highly electronegative atom such as fluorine or oxygen on an adjacent carbon can significantly change the pKa. Another feature than can modify the acidity of a proton is a double bond on the carbon to which the proton is attached. Both features increase the acidity of the proton, reducing its pKa value.

Answer 6

Chapter 6, Problem 6.52P

Interpretation Introduction

Interpretation:

It is to be determined in which of the four molecules A-D the pKa value of the OH proton is expected to be most similar to that of cyclohexanol.

Concept introduction:

The acidity of a proton depends primarily on the functional group to which it belongs. Nearby structural features can modify the acidity. A highly electronegative atom such as fluorine or oxygen on an adjacent carbon can significantly change the pKa. Another feature than can modify the acidity of a proton is a double bond on the carbon to which the proton is attached. Both features increase the acidity of the proton, reducing its pKa value.

Answer 7

Chapter 6, Problem 6.52P

Interpretation Introduction

Interpretation:

It is to be determined in which of the four molecules A-D the pKa value of the OH proton is expected to be most similar to that of cyclohexanol.

Concept introduction:

The acidity of a proton depends primarily on the functional group to which it belongs. Nearby structural features can modify the acidity. A highly electronegative atom such as fluorine or oxygen on an adjacent carbon can significantly change the pKa. Another feature than can modify the acidity of a proton is a double bond on the carbon to which the proton is attached. Both features increase the acidity of the proton, reducing its pKa value.

Answer 8

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Answer 9

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Answer 10

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Answer 11

Ch. 6 - Prob. 6.1P Ch. 6 - Prob. 6.2P Ch. 6 - Prob. 6.3P Ch. 6 - Prob. 6.4P Ch. 6 - Prob. 6.5P Ch. 6 - Prob. 6.6P Ch. 6 - Prob. 6.7P Ch. 6 - Prob. 6.8P Ch. 6 - Prob. 6.9P Ch. 6 - Prob. 6.10P

Solution Summary: The author explains that the acidity of a proton depends primarily on the functional group to which it belongs. Nearby structural features such as fluorine or oxygen can modify the pKa.

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Chapter 6 Solutions