Question

Nitration of Methylbenzoate. Lab 1

6. Why is it important to maintain the reaction temperature low and the addition of nitric acid-sulfuric acid mixture carried out slowly?

8. Which ring of phenyl benzoate would you expect to undergo nitration more easily? Explain.

9. Which is nitrated faster, toluene or phenol? Explain.

phenol or nitrobenzene

methyl benzoate or phenol

nitrobenzene or methyl benzoate

benzene or toluene

10. Show all mono, di and trinitration products of toluene. Do you think the mononitration products of toluene would be easy to isolate and identify all of them if each was produced in some amount?

11. Draw the mechanism for nitration of toluene.

Answer 1

The reaction is maintained at low temperature with slow addition of the HNO_3/H_2SO_4 mixture to ensure that only one NO_2 group is substituted (Mono nitration) If the temperature is high & the nitronium ion concentration is also too high then that leads to unwanted di (or) tri nitrated products Nitration of phenol is faster than tolence because �OH is strong ring activating group due to + M. E effect (mesomeric effect) phenol nitration is faster than nitrobenzene phenol nitration is faster than methylbenzoate Toluene nitration is faster than benzene