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Synthesis of Hippuric Acid
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Topic: Synthesis of Hippuric Acid (Read 15975 times)
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flumen22
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Synthesis of Hippuric Acid
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on:
April 20, 2010, 11:39:01 AM »
When making Hippuric acid from glycine, NaOH, and Benzoyl Chloride; why do the glycine and the NaOH base have to be mixed before adding the benzoyl choride? What purpose does the NaOH have in the overall reaction?
Thanks for any *delete me*
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sjb
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Re: Synthesis of Hippuric Acid
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Reply #1 on:
April 20, 2010, 03:33:53 PM »
What is the structure of glycine?
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flumen22
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Re: Synthesis of Hippuric Acid
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Reply #2 on:
April 20, 2010, 06:14:02 PM »
http://www.chm.bris.ac.uk/webprojects2006/Lovelock/800px-Glycine-skeletal.png
It's basically this, except the NH2 is actually NH3
+
and the OH is actually a H
-
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Doc Oc
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Re: Synthesis of Hippuric Acid
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Reply #3 on:
April 22, 2010, 08:25:56 AM »
You answered your own question (sort of). In a neutral environment the amine of glycine will be protonated because the pKa is above the pH of water. That means the lone pair is tied up with a proton, so you add the NaOH to make the environment basic enough to free that lone pair so it can attack the benzoyl chloride.
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