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Topic: Reaction help with nitrogen  (Read 2710 times)

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Offline Juwar74

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Reaction help with nitrogen
« on: August 26, 2010, 04:16:39 AM »
What product is form when CH3(CH2)3NH2 reacts with
CH3CO2C2H5?  I thought the nitrogen will react with the carbon that
has the double bond oxygen and water would be eliminated, but this is wrong.  If someone could draw the product I would really appreciate it.  I've tried several answers but none of them were correct.
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Offline Cancer Boy

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Re: Reaction help with nitrogen
« Reply #1 on: August 26, 2010, 05:41:03 AM »
You're along the right lines in thinking that the amine attacks the carbonyl and an amide is formed, but water isn't eliminated.

Think about what is eliminated when an amine and a carboxylic acid (ROOH) react. Now think what would be eliminated when an amine and an ester (ROOR) react.
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Offline discodermolide

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Re: Reaction help with nitrogen
« Reply #2 on: August 26, 2010, 01:48:18 PM »
you get an acetamide
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Offline discodermolide

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Re: Reaction help with nitrogen
« Reply #3 on: August 28, 2010, 02:48:51 AM »
Quote from: Juwar74 on August 26, 2010, 04:16:39 AM
What product is form when CH3(CH2)3NH2 reacts with
CH3CO2C2H5?  I thought the nitrogen will react with the carbon that
has the double bond oxygen and water would be eliminated, but this is wrong.  If someone could draw the product I would really appreciate it.  I've tried several answers but none of them were correct.

the product is CH3CONH(CH2)3CH3 that is elimination of ethanol. This reaction usually requires heat and a catalyst, DMAP or NaCN are good catalysts for this process
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