Explain, giving reasons, why:
i) phenol has a smaller dipole moment than methanol;
ii) phenol undergoes electrophilic substitution reactions.
i) phenol has a smaller dipole moment than methanol;
ii) phenol undergoes electrophilic substitution reactions.
Solution
(i) In CHOH the full C–O and O–H polarities add up. In phenol the oxygen donates its lone pair into the ring (resonance), creating an opposing charge displacement, and the C(sp)–O bond is itself less polar — the vectors partly cancel, so phenol's dipole moment (≈1.54 D) is smaller than methanol's (≈1.71 D).
(ii) The +M donation makes the ring electron-rich, especially at the ortho and para positions — electrophiles (Br, NO) attack there readily; phenol is far more reactive than benzene in electrophilic substitution.
(ii) The +M donation makes the ring electron-rich, especially at the ortho and para positions — electrophiles (Br, NO) attack there readily; phenol is far more reactive than benzene in electrophilic substitution.
CBSE Class 12 Board · 2002 · Delhi · Subjective