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Chemistry / Organic Chemistry 2 / Chapter 22 / Problem 22.58

Organic Chemistry | 2nd Edition | ISBN: 9781118454312 | Authors: David R. Klein

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One of the compounds from the previous problem has pKa<10.

Chapter 22, Problem 22.58

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QUESTION:

One of the compounds from the previous problem has pKa<10. Identify that compound and explain why it is so much more acidic than all of the other compounds.

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QUESTION:

One of the compounds from the previous problem has pKa<10. Identify that compound and explain why it is so much more acidic than all of the other compounds.

ANSWER:

Step 1 of 3

The structure of the compound as follows:

We are told that one of these compounds has a pKa < 10. We are asked to identify that compound and to explain why it’s so much more acidic than the other compounds.

Recall that pKa is a measurement of acidity. If the pKa value is low, then the compound more acidic. Water has pKa of about 16. It’s a logarithmic scale, so each integer change represents a ten-fold change in acidity.

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