For the given molecule, "x", the preferred site for the attack of the electrophile is : [figure]
- Predominantly at "r"
- "r" and "u"
- "p" and "s"
- Predominantly at "u"
Answer
(4) Predominantly at "u"
Solution
x is benzanilide, C6H5CO-NH-C6H5.
Ring bearing p and r (benzoyl ring): attached to C=O, an electron-withdrawing group ⇒ this ring is deactivated (and C=O is meta directing), so p and r are not preferred.
Ring bearing s and u (anilide ring): attached to N, whose lone pair is donated into the ring by resonance ⇒ this ring is activated and ortho/para directing.
(The lone pair is also shared with C=O, so activation is moderate — just as in acetanilide.)
s is ortho and u is para to –NHCOPh. ∵ –NHCOPh is a bulky group, attack at the ortho position s is sterically hindered.
As per NCERT, acetanilide on bromination gives p-bromoacetanilide as the major product; in the same way here
∴ the electrophile attacks predominantly at the para position u.
Answer: (4)