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Ways to separate 2-methylaniline and methylbenzene?

Ways to separate 2-methylaniline and methylbenzene?
what is the way to separate 2-methylaniline and methylbenzene ? option1 : nitrous acid option2: dilute hydrochloric acid...
the ans is option2: dilute hydrochloric acid...


why cant be option1 : nitrous acid??
Reply 1
Avatar for wilson dang
wilson dang
OP
7
Ways to separate 2-methylaniline and methylbenzene?

what is the way to separate 2-methylaniline and methylbenzene ? option1 : nitrous acid option2: dilute hydrochloric acid...
the ans is option2: dilute hydrochloric acid...


why cant be option1 : nitrous acid??
Original post by wilson dang
Ways to separate 2-methylaniline and methylbenzene?

what is the way to separate 2-methylaniline and methylbenzene ? option1 : nitrous acid option2: dilute hydrochloric acid...
the ans is option2: dilute hydrochloric acid...


why cant be option1 : nitrous acid??


... because nitrous acid will react with the amine group forming first the diazonium ion intermediate and then phenol ... (or in this case o-cresol)
(edited 9 years ago)
Reply 3
Avatar for GDN
GDN
1
methylbenzene wont react with either of those reagents whereas 2-methylaniline will react with both - the difference is that the reaction with nitrous acid makes a new substance (initially the diazonium ion) whereas the reaction with dil HCl merely protonates the amine making it water soluble so it will dissolve in the HCl - the methylbenzene being immiscible - the layers can then be separated and the aniline regenerated by adding NaOH(aq)

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