Question

Comment on the orientation, hybridization (pure P) and degree of conjugation of the N-atom lone pair in p-toluidine influences the 1HNMR chemical shifts of the 1H atoms ortho and meta to the amino group relative to benzene. Include resonance structure in your answer

piesén nts tne electronic structure of the imine N-atom. (3 pts) re.. no hybrid H2 p-toluidine CS model imine C1

Answer 1

NH2 is +M , +R and +I group it donates electron density to the ring and increase the electron density at ortho and para position of the ring while meta position is less affected. chemical shift normally for aromatic ring hydrogen is = 7.37 ppm in 1H nmr but in presence of NH2 group the electron density increased at ortho and hence ortho and para hydrogen shifted to slightly upfield to 6.7 ppm , while meta shifted to slight lesser than ortho and para to 7.2 ppm .

please find attached file for detailed information

For Resonana CH NH2 H2 CH C H3 3 During Resonane, heu i NH2 4 Hydogen - 가31 at ortho Pasa to-NH2 valul chenges @f nohe. Fwm m37 h..r1.2 fph 12PP