2444-110211

2444-110211 - 1 Dicarboxylic acids Structure !HOOC-COOH!...

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Dicarboxylic acids 1 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 HOOC-COOH HOOC-CH 2 -COOH HOOC-(CH 2 ) 2 -COOH HOOC-(CH 2 ) 3 -COOH HOOC-(CH 2 ) 4 -COOH HOOC-(CH 2 ) 5 -COOH HOOC-(CH 2 ) 6 -COOH HOOC-(CH 2 ) 7 -COOH HOOC-(CH 2 ) 8 -COOH 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 acid Derivatives 2 • Derivatives with only one chlorine (a half-acid chloride 145 ) or two chlorine atoms (a diacid dichloride; 146 , actually called an acid dichloride) are possible. • Similarly, a half-ester can be formed ( 147 ) or a diester ( 148 ). In reactions of simple dicarboxylic acids such as 1,3-propanedioic acid (malonic acid, 149 ) with thionyl chloride, it can be difFcult to generate only the half-acid chloride, 150 (malonyl chloride). • Normally, the acid dichloride ( 151 , malonyl dichloride) is formed by this reaction. OH OH O O 2 SOCl 2 OH Cl O O Cl Cl O O 149 150 151 major Cl (CH 2 ) n OH O O Cl (CH 2 ) n Cl O O OR (CH 2 ) n OH O O OR (CH 2 ) n OR O O 145 146 147 148
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Dicarboxylic acid Derivatives 3 OH OH O O OEt OEt O O OH OEt O O 152 153 154 excess EtOH major cat. H + Cl Cl O O MeHN NHMe O O excess MeNH 2 155 156
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Oxalyl Chloride 4 O OH Cl O O Cl NEt 3 O Cl + 157 158 45 • There is one acid dichloride (acid dichloride) that is extremely useful, oxalyl chloride ( 157 ). • When 157 reacts with a carboxylic acid such as pentanoic acid ( 45 ), in the presence of an amine base (such as triethylamine), the acid is converted to an acid chloride (in this case pentanoyl chloride, 158 ). Reaction with oxalyl chloride is a very efFcient and very mild method for converting acids to acid chlorides.
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5 OH OH O O O O O OEt OEt O O N O O H heat cat. H + , EtOH 152 159 153 160 NH 3 , heat N N O O Cl O O Br 161 162 • Imide 161 is known as N- chlorosuccinimide (NCS) and 162 is N- bromosuccinimide (NBS). • Imide 161 is used as a chlorinating reagent (converts a molecule to a chloride), and is particularly useful in radical substitution reactions. • Similarly,
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2444-110211 - 1 Dicarboxylic acids Structure !HOOC-COOH!...

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