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8 August, 09:28

4-dimethylaminopyridine (DMAP; below) is an extremely useful molecule in organic chemistry. One professor here at OSU often comments to graduate students when theirreaction isn't working just to sprinkle a little DMAP into their reaction. Which nitrogen atom of DMAP is most nucleophilic? Use drawingsanda minimumamount of wordsto support your answer.

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  1. 8 August, 09:30
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    Nitrogen A would be more nucleophilicity (figure 1.)

    Explanation:

    In the DMAP molecule we will have 2 nitrogens label as "nitrogen A" and "nitrogen B". For nitrogen B we will have more steric hindrance due to the 2 methyls groups and the benzene ring. What will hinder the attack from this nitrogen (nitrogen B) to an electrophile. On the contrary, the attack of nitrogen A could easily occur.
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