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3 Handout (Estimating acidity)

3 Handout (Estimating acidity) - How to identify the most...

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How to identify the most acidic proton Introduction: Most molecules contain different types of protons (attached hydrogens). However, when acting as acids, only the most acidic proton will participate in the acid-base reaction. Therefore, it is important to be able to identify the most acidic proton in a molecule. How to: There are three basic methods of trying to estimate the acidity of a proton: 1) Use the table of common acids that we learned in class and is in your book (Table 3.1, inside front cover of the book), and try to either find the same acidic proton or similar one in the table. 2) Identify which functional group the proton is a part of like: alkane, alcohol, carboxylic acid, protonated amine, etc... Make sure that the proton in question is actually part of the functional group and is not simply attached to atoms that are attached to the functional group. Here is a short list of acidities of common functional groups in organic chemistry (Note: that the pKa's are an approximate value for that functional group.) Functional group
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