Organic Chemistry
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Dr. Brian
Pagenkopf |
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The following table lists the pka of compounds we commonly use in class. If you memorize this table, it will make understanding more of organic chemistry easier.
Alkanes |
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51 |
Amines |
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33-35 |
Esters |
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23-25 |
Ketones and aldehydes |
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18-20 |
Alcohols |
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15-19 |
Water |
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15.7 |
b-Ketoesters |
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11 |
b-Diketones |
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10 |
Carboxylic acids |
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3-5 |
Why are the b-Ketoesters and b-Diketones so much more acidic than their ketone and ester counterparts? Resonance stabilization.
Note how the negative charge is spread evenly over both carbonyls:
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