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Thread: Glycine and ammonia

  1. #1 Glycine and ammonia 
    Forum Freshman chicken_boy's Avatar
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    what are the products formed when glycine reacts with ammonia? I guessed that the products should be an amide and water but I need to know the exact products and the catalyst, if used.


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  3. #2  
    Him
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    The ammonia can act as nucleophile and perform an addition/elimination reaction in the carbonyl.

    the picture of wikipedia is the thing your looking for



    Nu-: ammonia

    The Leaving groep (L) is the hydroxyl OH.

    water is created when OH- take the H+ from the ammonia on the carbonyl (stronger base).



    The reaction will not start in acid conditions

    here's the wikipedia link
    http://en.wikipedia.org/wiki/Nucleop...l_substitution


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  4. #3  
    Forum Freshman chicken_boy's Avatar
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    thank you!
    thats cleared up alot of confusion for me
    I know not with what weapons World War III will be fought, but World War IV will be fought with sticks and stones.
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  5. #4  
    VM
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    Just thought I would chime in here and say that the Scheme presented by Him is that for basic conditions. The reaction can also proceed under acidic conditions. In this case, the carboxyl oxygen will become protonated prior to the attack on the electrophilic carbon (carbonyl carbon). THe protonation of the oxygen makes the carbon a stronger electrophile allowing the nocleophile to attach. Consequently, you will end up with a carbon with two hydroxyls and an amine. One of the hydroxyls will be further protonated to form water, concomitant with its leaving upon reformation of the carboxyl.

    I think the normal reaction though is more effecient under basic conditions, which to no suprise are the conditions found in the body (blood is basic, i belive). Wich makes sense because this is basically the reaction used to condense two amino acids together (imagine the amonia was another glycine -- or any other amino acid).

    Some cool stuff.
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