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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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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