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Chemistry Forums for Students => Undergraduate General Chemistry Forum => Topic started by: ironnica on December 01, 2009, 08:44:59 PM

Title: protection of primary amine
Post by: ironnica on December 01, 2009, 08:44:59 PM

Hello one and all. here's one thing that is wrecking my head. for every experiment we do in organic chemistry we have to draw out the mechanism, in quite a bit of detail. This is the first week that I have been unable to find anything that can give me even a slight insight into the mechanism. Here it is anyway:

Title: Synthesis of 2-hydroxyphenylphthalamide, protection of a primary amine.

added phthalic anhydride and 2-aminophenol (reactants) to reaction flask with glacial acetic acid. refluxed for 1hr at 125oC. cool and filter.

seemed like a simple experiment, got a very good yield, but....

please help

Title: Re: protection of primary amine
Post by: stewie griffin on December 01, 2009, 09:13:14 PM

What do you know about the reactivity of anhydrides? Are the electrophilic or nucleophilic?
What about nitrogens with their lones pairs. Are they going to be nucleophiles or electrophiles?