kaplan ochem subject test 3

[Questions]

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how would you separate these: aniline, para-nitroaniline, nitromethane?

The answer is to first extract with a weak acid, then extract with stron acid, then distill.

My answer was: first extract with strong base, then extract with weak acid, then distill. How come this is wrong
?

 

[polola55]

how would you separate these: aniline, para-nitroaniline, nitromethane?

The answer is to first extract with a weak acid, then extract with stron acid, then distill.

My answer was: first extract with strong base, then extract with weak acid, then distill. How come this is wrong
?

aniline is very basic due to the strong activating/donating group. To get rid of aniline, you need to react w/ a strong base; Finally you can extract w/ a strong acid to react w/ p-nitroaniline to separate from nitromethane. They will have different bps (p-nitroaniline will have a higher bp than nitromethane) and can be distill