Monday, October 4, 2010

Ammonia alkylation

During the direct alkylation of ammonia, why do we need to add a base to get rid of the Br from CH3NH3Br?  Doesn't the Br come off by itself since N cannot be attached to 5 things?
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Here we need a base because we actually have an ionic salt of CH3NH3+ and Br-.  The base here deprotonates our NH3 group in the compound, thus making a neutral CH3NH2.  The Br- is no longer attracted, and thus comes off the molecule too.  The base is needed, though, to cause that deprotonation in the first place.

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