CHEM 281 Chapter Notes - Chapter 2: Conjugate Acid, Substituent, Electronegativity

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Chapter 2 notes part 7: acids and bases. 2. 7: how substituents affect the strength of an acid. The different pka values indicate that there must be another factor that affects acidity other than the atom to which the hydrogen is bonded. The halogen is more electronegative than the hydrogen it has replaced, so the halogen pulls the bonding electrons toward itself more than a hydrogen would. Pulling electrons through sigma (s) bonds is called inductive electron withdrawal. If we look at the conjugate base of a carboxylic acid, we see that inductive electron withdrawal decreases the electron density about the oxygen that bears the negative charge, thereby stabilizing it. And we know that stabilizing a base increases the acidity of its conjugate acid. The pka values of the four carboxylic acids shown above decrease (become more acidic) as the electron- withdrawing ability (electronegativity) of the halogen increases.

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