Low-molecular-weight dicarboxylic acids normally exhibit two different pK, values. Ionization of the first carboxyl group is easier than the second. This effect diminishes with molecular size, and for adipic acid and longer chain dicarboxylic acids, the two acid ionization constants differ by about one pK unit. Dicarboxylic Acid Structural Formula pK,2 a1 Охalic НООССООН 1.23 4.19 Malonic НООСCH,COOH 2.83 5.69 Succinic HOOC(CH,),COOH 4.16 5.61 Glutaric HOOC(CH,),COOH 4.31 5.41 Adipic HOOC(CH,),COOH 4.43 5.41 Why do the two pK, values differ more for the shorter chain dicarboxylic acids than for the longer chain dicarboxylic acids?

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Low-molecular-weight dicarboxylic acids normally exhibit two different pK, values.
Ionization of the first carboxyl group is easier than the second. This effect diminishes
with molecular size, and for adipic acid and longer chain dicarboxylic acids, the two acid
ionization constants differ by about one pK unit.
Dicarboxylic Acid
Structural Formula
pK,2
a1
Охalic
НООССООН
1.23
4.19
Malonic
НООСCH,COOH
2.83
5.69
Succinic
HOOC(CH,),COOH
4.16
5.61
Glutaric
HOOC(CH,),COOH
4.31
5.41
Adipic
HOOC(CH,),COOH
4.43
5.41
Why do the two pK, values differ more for the shorter chain dicarboxylic acids than for
the longer chain dicarboxylic acids?
Transcribed Image Text:Low-molecular-weight dicarboxylic acids normally exhibit two different pK, values. Ionization of the first carboxyl group is easier than the second. This effect diminishes with molecular size, and for adipic acid and longer chain dicarboxylic acids, the two acid ionization constants differ by about one pK unit. Dicarboxylic Acid Structural Formula pK,2 a1 Охalic НООССООН 1.23 4.19 Malonic НООСCH,COOH 2.83 5.69 Succinic HOOC(CH,),COOH 4.16 5.61 Glutaric HOOC(CH,),COOH 4.31 5.41 Adipic HOOC(CH,),COOH 4.43 5.41 Why do the two pK, values differ more for the shorter chain dicarboxylic acids than for the longer chain dicarboxylic acids?
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