2444-100311

2444-100311 - 1 Dicarboxylic Acids A dicarboxylic acid is...

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Dicarboxylic Acids 1 • A dicarboxylic acid is named as a dioic acid . The IUPAC nomenclature requires that the longest chain contain the carbonyl carbon of both carbonyl groups, the chain is numbered to give both carbonyl carbons the lowest possible number, and the ending is dioic acid. 45 is 1,2-ethanedioic acid (or just ethanedioic acid since that is the only possibility). Common name is oxalic acid 46 is 1,3-propanedioic acid (or just propanedioic acid) Common name is malonic acid 47 is 1,4-butanedioic acid Common name is succinic acid 48 is 1,5-pentanedioic acid. Common name is glutaric acid HO OH O O HO OH O O HO 2 C CO 2 H HO 2 C CO 2 H 45 46 47 48
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Dicarboxylic Acids 2 HO 2 C–CO 2 H HO 2 C–CH 2 –CO 2 H HO 2 C-(CH 2 ) 2 –CO 2 H HO 2 C-(CH 2 ) 3 –CO 2 H HO 2 C-(CH 2 ) 4 –CO 2 H HO 2 C-(CH 2 ) 5 –CO 2 H HO 2 C-(CH 2 ) 6 –CO 2 H HO 2 C-(CH 2 ) 7 –CO 2 H HO 2 C-(CH 2 ) 8 –CO 2 H oxalic acid malonic acid succinic acid glutaric acid adipic acid pimelic acid suberic acid azelaic acid sebacic acid 1,2-ethanedioic acid 1,3-propanedioic acid 1,4-butanedioic acid 1,5-pentanedioic acid 1,6-hexanedioic acid 1,7-heptanedioic acid 1,8-octanedioic acid 1,9-nonanedioic acid 1,10-decanedioic acid S t r u c t u r e C o m m o n N a m e I U P A C N a m e
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Dicarboxylic Acids 3 • 49 has an 11-carbon chain that contains both carboxyl units, so it is a 1,11-undecanedioic acid. • The substituents are given the lowest sequence of numbers, so the name of 48 is 2,3-diethyl-10-propyl-1,11-undecanedioic acid. CO 2 H CO 2 H 49
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Dicarboxylic Acids 4 • 50 is but-2 Z -en-1,4-dioic acid and 51 is but-2 E -en-1,4-dioic acid. • The common name of 50 is maleic acid and 51 is known as fumaric acid. • Compound 52 does not have a common name, but using the IUPAC system it is 2-ethyl-8-methylnon-3 E -en-1,9-dioic acid. CO 2 H HO 2 C HO 2 C CO 2 H CO 2 H CO 2 H 50 51 52
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Dicarboxylic Acids Have Two pK a Values 5 An interesting feature of dicarboxylic acids ( 53 ) is the presence of two acidic hydrogen atoms, which means there are two pK values , pK 1 and pK 2 .
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This note was uploaded on 02/25/2012 for the course CHEM 244 taught by Professor Jardin,j during the Fall '08 term at UConn.

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2444-100311 - 1 Dicarboxylic Acids A dicarboxylic acid is...

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