Quick deprotonation question

  • Thread starter bomba923
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Main Question or Discussion Point

Why is it that when methylamine ([tex] CH_3 NH_2 [/tex]) loses a proton,

you get [tex] CH_3 NH [/tex] (with a negative charge on nitrogen) rather than [tex] CH_2 = NH_2 [/tex] (with a positive charge on nitrogen) ?
 

Answers and Replies

GCT
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So you're basically saying that an intramolecular proton transfer will occur, either that or you're basically asking on why the carbon hydrogen in less acidic then the one on the amine. If it is in reference to the latter...read you text. The intramolecular reaction does not occur appreciably (to my knowledge) because the conjugate anion is a stronger base than even the amine hydrogen.
 
movies
Science Advisor
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Think in terms of electronegativity. Which atom is more likely to bear a negative charge?
 

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