When three isomeric chlorotounes are treated with KNH_(2) in liquid NH_(3), they yield different toluidines as shown below. Explain these observations. ltrgt a. o- Chlorotouene rarr (o : m)- Toluidine b. m- Chlorotouene rarr (o+ m + p)- Touidine c. p- Chlorotouene rarr (m +p)- Touidine

When three isomeric chlorotounes are treated with KNH_(2) in liquid NH

1.	When three isomeric chlorotounes are treated with KNH_(2) in liquid NH_(3), they yield different toluidines as shown below. Explain these observations. ltrgt a. o- Chlorotouene rarr (o : m)- Toluidine b. m- Chlorotouene rarr (o+ m + p)- Touidine c. p- Chlorotouene rarr (m +p)- Touidine
Answer» Solution :The REACTION involeves aryene intermidediates. In `o-` chlorotouene. Only one `o-` hydrogen is avaiable and so its elimination generates only one `o-` hydrogen is availableand so its elimination generates only one aryne, whereasthe availity of two `o-` hydrogents in `m-` chlorotoulnee generates two aryenes. ALTHOUGH two `o-` hydrogens are available in `p-` chlorotouene, THIER elimination generates only one aryene.