19- 13 Cl �-oo � :OCH3 I _0_0 __ .. N 19- 14 (a) � / -0 0 � _jlC:NH� N Br cj;�-o�H�5Hl N _N N GOOD stabilized by induction from nitrogen �NH2 (jib:, NH: N -�GOOD -Cl� �' N This is a benzyne-type mechanism. (For simplicity above, two steps of benzyne generation are shown as one step: first, a proton is abstracted by amide anion, followed by loss of bromide.) Amide ion is a strong enough base to remove a proton from 3-bromopyridine as it does from a halobenzene. Once a benzyne is
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