Question

(a) How do you convert the following :
(i) Phenol to Anisole
(ii) Ethanol to Propan-2-ol
(b) Write mechanism of the following reaction :
$C_2{H}_{5}OH\stackrel{H_{2}S{O}_4/443K}{\to }C{H}_2=C{H}_2+H_{2}O$
(c) Why phenol undergoes electrophilic substitution more easily than benzene?

Answer 1

(a) i.

ii. Etahnol when reacted with PCC(Pyridinium chlorochromate) will get converted to acetaldehyde and when it is reacted with $Me-Mg-Br/hydrolysis$ will form propan-2-ol.
$C{H}_{3}C{H}_{2}OH+\stackrel{PCC}{\to }C{H}_{3}CHO$
$C{H}_{3}CHO+\stackrel{Me-Mg-Br/H_{2}O}{\to }C{H}_{3}CHOHC{H}_3$
(b)
(c) OH group in phenol will exert +R and -I effect so it will enhance the electron density on ortho and para position and will reduce electron density on meta position hence it will increase the activity of ortho and para position for electrophilic aromatic substitution.