of
aniline is more than that of methylamine.
(ii) Although amino group is o-and p-directing in aromatic electrophonic
substitution reactions, aniline on nitration gives a substantial amount of m-nitro
aniline. [2]
Answer:
(i)
Smaller the value of 
,
larger the value of
.
Basic character of 
is due
to lone pair of N-atom. In aniline (A) electron-density at N-atom is decreased as
this lone pair is used in delocalisation of Ti-electrons in benzene nucleus.
Thus, 
is less
basic than
group
is electron donating group. This increases electron density at N-atoms. Thus, 
is more basic
than 
, Hence
Thus,
[1]
(ii) Nitration is done using HN03 (after protecting 
group
by acetylation) group
increases electron-density at o- and p-sites as shown
Due to presence of 
group
is acidified
and thus
group is
now, electron-withdrawing making benzene nucleus electron-deficient at o- and p-sites
and only m-sites available but with decreased reactivity.
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