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How does sodium react with phenylamine ? Help !!!!

In a june 2013 paper (f214), there was this question and I expected the answer to be the compound that you can see in the top right of the picture attached, but instead that was an incorrect answer. In the correct answer, the NH2 group did not react with the H+ Ion which was produced from the OH/Na reaction. Why is this??
Reply 1
This is what the markscheme says for this question.
Hmmm I don't think phenylamine is very basic because the lone pair on nitrogen is delocalised into the conjugated ring. This makes the lone pair less available and less basic, so it wont be protonated.
Try writing out a balanced equation for the reaction, remembering that charge is conserved. :yep:
(edited 10 years ago)
Reply 4
Original post by EierVonSatan
Try writing out a balanced equation for the reaction, remembering that charge is conserved. :yep:



OOHHHHH

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