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Topic: Synthesis of Hippuric Acid  (Read 15975 times)

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Offline flumen22

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Synthesis of Hippuric Acid
« 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?

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Offline sjb

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Re: Synthesis of Hippuric Acid
« Reply #1 on: April 20, 2010, 03:33:53 PM »
What is the structure of glycine?

Offline flumen22

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Re: Synthesis of Hippuric Acid
« 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-

Offline Doc Oc

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Re: Synthesis of Hippuric Acid
« 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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