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Unformatted text preview: localized on a larger atom. The negative charge is “spread out” over a larger volume, which stabilizes the anion. For this reason, the thiol is more acidic than the alcohol. The thiol that also contains a chlorine substituent is more acidic than the thiol that lacks a chlorine substituent, due to the inductive effect caused by the electronegative chlorine atom. (c) E x p l a n a t i o n : H As(CH 3 ) 2 H As(CH 3 ) 2 H H N(CH 3 ) 2 2 3 1 Considering the same element, positively charged molecules are more acidic than neutral molecules (the conjugate base is a neutral molecule which is more stable than an anion). As stated above, when moving down a column, acidity increases, because localization of the negative charge on a larger atom stabilizes the conjugate base anion....
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This note was uploaded on 07/16/2008 for the course CH 310M taught by Professor Iverson during the Spring '05 term at University of Texas at Austin.
- Spring '05