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in"
1
CHEMISTRY
yifa+ 4ifn+(Aromatic Compounds)
sf4
(1) ( = ~- + i ln+i +i ai- l+i i - +i t . i i+ l-+ -zii -i = i-- ti - t = l-. in=n. ( i n l+ - n :il<.
-ii l-t - -zi = (+ lzi i +i + i ln+i + =n t l-t (i n l+ i ln+ +t- t . (n i+. (i ni. = nl-i- i zi ) n
ni+ - l+i i =+-i t
(2) (ln+ l+ ti: i +i - i ln+i +i ~ -ii (i n l+ i ln+i n +i - +i l-zi- nizii ~ili+ ti -i t == =iiii
(inl+ i ln+i n ii +n = +n z +i - nii -l-i- t- t
t ii ni t l+ (i n l+ i ln+i +i llii ,ii ~li+ - (treatment) l+i i-i t -i -i- ( -=+ --
-i< + n i-- ti- t
(3) -i- n +- (i n l+ i ln+ -i-i : i ln+ (benzenoid compounds) +tni- t i ln+ -l+ ti - t .
l+-- :-+ n i (ln=i:l+n+ i ln+i = i -t li-- ti- t
(4) =in ii ni ,ii (1870) nin--- -ni (=ilni- +i ilt- + -i- +i =zn ii l+i ni
3C
2
H
2
C
6
H
6
+ ~- -i<
(5) =ini-- n = -i- +i (i n l+ ~-ni + l+ii +=ini+i ,ii i-- l+i i-i t -<iti + ln l---
i=il-+ ~lil+i ,ii <lzi - t . l+ -i :+ ~-n ( iln+ ~-n +i + l-zin ~i+=i:=i ini:n +i -l-il-
n nn +- -i- i-- ti-i t
COOH

) CaO ( NaOH

) CaO ( NaOH
1. yifa+ n+ii [r+n 4n + 2 fa4]
t+n + ~- =i l---lnli- -i- l-n l+=i ii llzi i ln+ +i (in l+ i -i-(in l+ <lzi - +- n =ti+
ti- t
1. (inl+ iln+ -l+ ( =n-ni ti- t
2. (inl+ n n + nii sp
2
=+l- ti-i t
3. -l+ t ~iil+ +-i+i n (4n + 2) t :n+ i- ti - -ilt ~ii- 2, 6, 10, 14 ........ t :n+i- ti - -ilt
ti n = (+ i+- =i 0, 1, 2, 3,..............
yifa+ai +i iif+ ++i+ fu&i-a
~iil+ +-i+ l=zi-- (MOT) + ~- =i -i- (+ l-ln- =n-ni i +n+i = --i t l=n + +i - nii
lzi+n+i = +i ~-ii n t-i t ~- -i- n z C Hl=nni i z C Cl=nni. i. ( z 2p
z
:n + i - ( +
+i - nii (+ :n + i -) ti - t . i n + =ni-- ( n-- -n n l-i- ti - t :n + i- l--- l-zii- =i
(b) ( (c) + ~- <i +i = (+ < = = ln- ti =+- t + 2p
z
:n + i- ~- l-+-n <i -i ~i + =<-i
= =ni- = ~l-il- ti -i t l=+ +n- =ii z 2p
z
:n + i- (+ ~iil+ +-i+ (M.O.) +i -t <lzi -
l+ i =+- t
(a) (b) (c) (d)
~i ~-ii (ground state) n -i- l-ii-i+- (delocalised) i: :n+i- ni +i +n -i. -i- -ii-i+-
(localised) i: :n+i- ni (b) i (c) +i ~ -ii +n ti-i t ~- +ti i =+-i t l+ -i- ~i l-ii-i+i
(~- -i<) ,ii -iil i-- +-i t
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2. yifa+ 4ifn+i +t y+ta 4ifn+i + uii anai
-i- ,ii. (-+i-i + =ni- i l+ =ini- +n + -ini- i ni- + =ii ziii -i = ~lil+i + i nin+ -i<
-i-i t . l+iziin-i <lzi - -ti +i i-i -<iti + ln =i:+ni t +=i- +i ini- + =ii ~lil+i + +n-
l-i-1, 2-i:ini=i:+nit+=- -i< + n i-- ti-i t t ~lil+i -ni -ii (exothermic) ti-i t. -ii
~lil+i + ln AH +i ni- nnin 29 kcal/mol (121 kJ/mol.) ti -i t
+ Br
2
AH = 29 kcal ( 121 kJ)
:=+ li- -i +- =ni- ll-il-i n -i- +i i ni- + =ii ~lil+i -nizii ii (endothermic) ~lil+i ti -i
t +i l+ :=+i ~iz+-i (i n l+ n + (i n l+ -iil +i +n +- + ln ti -i t =ini- ll-i-i n -i-
+ =ii i ni- +i ~lil+i i nin+ ~lil+i - ti + l-ii- ~lil+i ti -i t l=n -i- n n = (+ ti: i -
nii +i i ni- nii ,ii l--ii- ti -i t -ii (i n l+ -i< i-- ti -i t t l--ii- ~lil+i -ni-i i ti -i
t n l+- ~lil+i n (+ n : = ~-n - + +i ~iz+-i ti -i t . i i ni- +i (+ -i :n + i--- ti n ll- -
+ =+
+ Br
2
AH = + 2 kcal (+ 8kJ)
+ Br
2

3
FeBr
+ HBr AH = 10.8 kcal ( 45 kJ)
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yifa+ 4ifn+i + a<iri : (aifn+i )
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3. -ta n4 rnaia art sfaiisa fif+4iy
(-+i- + =ni-. -i- n ii l=ni i - zi + - ( -i- i: :n + i- ~i l-i- ti -i t l -i- n -l-i-
i: :n + i- (i n l+ - zi n -iii ti- t . l+ ii (+ -i :n + i- -- ti ti +- + ln -ni t- t
-ii +i i-i- -i- t . t ~- -i< -iii+ - +i i-i- l=ni = + n +tni-i t +i l+ :n + i - -- ti +i -i- n
= n- (+ - l=ni i ,ii ti -i t l=ni = + n i l+ (ll-n ~i- ii +tni-i t . (i n l+ -ti ti -i +i l+
:=n sp
3
= +l- +i - nii p +-i+i +i n + n l- <i +- t l-ln - l=ni = + n n ( i n l+-i +i ri=
= + n ~lil+i + in < + --- -nizii ii l-i +i <lzi - +-i t -ii := l=ni = + n ,ii (i n l+-i +i i
-i in < +i li- +n n <i ti+ (~li+i+i +i < +) i l+ -- +n+i +i - nii = i i- + l-+i=-
,ii l--iil- -i< -i+ = l-i- ii i-i t ~- liiln+ = (in l+ n n = (+ i i - +i :n+ i-
-- ti ~li+n+ ,ii l--ii- ti-i. :n+i---ti (inl+ l--ii- ~lil+i +tni-i t
s< 1 : -i- n (+ :n +i- -- ti ~li+n + + ti ,ii (+ l=ni =+n i-- ti -i t
H E
H E
~--i<i =+
[ o =+n]
(il-n ~i-]
s< 2 : l=ni =+n n = ii- + l-+i=- + +n- l--iil- -i< i-- ti-i t
H E

O
: Nu
E
+ Nu H
4. uf+4+ ur 4i rnaia sfa+it ur (ERG)
=ii =n t l- (+ i <i (+i+i :n + i - n -l-i- ti - t . =l++ =n t +tni- t . +i l+ :- =n ti + -ili+
n --- :n + i- i- ti-i t ~- :-+ ,ii :n + i-i +i <i- +- + +n- - zi +i -i n lz ti -i t -ii
-- =l+i -i + +ii ~lil+i +i < n lz ti-i t -<iti + ln
> > > > > OR > > Ar > R
~- =ii =nt i :n+i-i +i <i- +- in ti- t ( ~il<) ~iii ( i
l-l<+ii ti- t ( -i- n n :n+i- --ti l--ii- ~lil+i =--- +i- t
a<i.1 l---lnli- ~iii ( i l-l< +ii =nti + =l+i iii +i -n-i + i-- +n +i - +il
(a) OH
..
..
,
O:
..
..
-
,
OC CH
3
..
..
||
O
(b)
2
. .
H N and
O
||
CH C H N
3
. .

a-i. (a) -i+- =nti +i =l+-i +i +n tini O
-
> OH > OCOCH
3
- l+ O
-
=n t i +iin+ ~i zi -l-i- t. ~- t =n-i = e
-
+i <i- ++ (+ ~li+ -iii -ii
l-i lzi- n-i -i-i t
E
H
O
(b)
Ar N = C CH
3
| |
H :O:
..
-
(ni: n +i== n- (cross-conjugation) + +ii -i +- =n ti +i =l+-i +i l--- +n
ti -i t
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2
. .
H N >
O
||
CH C H N
3
. .

6. uf+4 ur 4i rnaia i+it ur(EWG)
=nt i -i- + -ili+ = t :n+i-i +i ~-i ~i ~i+li - + :n+i- i- +i +n +- t -ii l=+
+n- -i- n n :n+i--- ti l--ii- +i < +n ti i-i t. ~=l++ i EWG=nt +tni- t
:n + i- ~i+ii =n ti +i -l-il- + liin- -i- n +i ~iii ( i l-il- :n + i- - - l+ n i l-il-
~li+ :n + i- i- +- ti -i t . ~- :n + i--- ti l--ii- ~lil+i -i- n +i ~iii ( i l-il-i -
ti+ n i l-il- =--- ti-i t
eg.
6. rniat+i
(a) -ta +i iiat+i :
i ni-i+i ~lil+i (+ =ini- :n + i--- ti (i n l+ l--ii- l+illi ,ii =--- ti -i t i ni-i+i ~lil+i
+ <i i- + n i ni-. -i- = ~lil+i t - (+ :n + i--- ti ~li+n + + n i -- -ti ti -i ~- (+ -i n : =
~-n = l+ FeBr
3
+i ~lil+i n - + + n -i n l+i i-i t
s< 1 : n :n+i---ti +i l-nii
Br :
:
: Br + FeBr
3
:
:: Br :
:
: Br
:
:
+
o
FeBr
3
:

o
s< 2 : -i- :n+i---ti ,ii ti + +n- (+ l=ni =+n +i l-nii ti-i t
Br :
:
: Br FeBr
3
:
::
+ H
H
H
H
H
H

+ FeBr
4

s< 3 : - -i < n l=ni = +n n = (+ i i- (H


+
) +i l-+i=- ti- + +n- l--iil- -i< i-- ti -i t
~lil+i + ~-- n- l=ni = + n +i l-ni i :=+i n l-ii + < ti -i t -ii -i +- -i l-zi n := ----n -i
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CHEMISTRY
l-< +- = +ni ~-ii ,ii <lzi- l+i i =+-i t < l-ii + < ~ili+ -nizii ii < ti -i t . +i l+ :=
< + ~--n- (+ -i-(inl+ +ii-i- --i t --i < -ni-ii ti-i t. +il+ := < + ~--n- -
(i n l+-i +i i-- l+i i-i t -ii HBr +i (+ ~i ii l-+il=- ti -i t liiln+ = i ni-i+i -ni-i i
~lil+i ti -i t . -ii ~lil+i + ln AH
0
+i ni- 10.8 kcal/mol (45 kJ/mol.) ti -i t
(b) -ta +i nitat+i
-i- +i +ni i-i+i ~lil+i i ni-i+i ~lil+i + =ni- ti ti -i t + n +ni i-i+i ~lil+i t - n
= ~li+i zi- n:= ~-n (AlCl
3
) +i - + + n -in l+i i-i t
+ Cl
2
3
AlCl
+ HCl
(c) -ta +i i4itat+i
-i- +i ~ii i-i+i ~lil+i t - ~-ni ~i+=i+i+ ~li+n + = l+ -i:l + ~-n +i ~iz+-i ti-i t
~lil+i + ~-- n- -i:l + ~-n +i =ini-- -i n + lni i-i t ~- +ti i =+-i t l+ -i:l + ~-n (+
- + + -ii- (+ ~li+n + ((+ ~i+=i+i+) +i -t -i n l+i i-i t
+
2
1
I
2
+ HNO
3
+ NO
2
+ H
2
O
=ini-- ~ii i-i+i +i ~lil+i ~ii i l-n

) (I + nin = :n + i--- ti (i n l+ l--ii- +i l+illi ,ii
=--- ti -i t ~ii i l-n ~i- -i:l + ~-n ,ii ~ii i- +i ~i +=i+i ~lil+i + +n- i-- ti -i t l=
l--- ~lil+i ,ii <lzi - l+i i =+-i t

H + HNO
3
+
2
1
I
2

u vk;
kfu;e s M vk;ks

I + NO
2
+ H
2
O
7. airat+i
-i: i+i ~lil+i + ln =i-< HNO
3
i -i: i+ii lni (=i-< HNO
3
+ =i-< H
2
SO
4
) +i -in l+i i-i t
~+ni =i-< HNO
3
<n -i:i+i+ ~li+n+ t l+ =i-< HNO
3
( =i-< H
2
SO
4
+i lni n -i:i+ii
~li+n + + n +i +-i t lni +i -i n +- (=i-< HNO
3
( =i-< H
2
SO
4
) = in -i: i l-n ~i-
(NO
2
+
) i-- ti -i t l= l--- ~lil+i ,ii <zii i i =+-i t

O H
3
+
HNO
3
+ 2H
2
SO
4
~nn < n -i: i l-n ~i- ,ii -i- + -ili+ ti ti -i t -ii (+ n-i i-i- i-- ti -i t ~l--n <
n := n-i i-i- n = (+ ii- +i l-+i=- ti- + +n- -i:i -- -i< + n i-- ti- t
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H
+
+
8. u+iat+i
-i- +i =-+i-i+i ~lil+i + ln =i-< =-+l+ ~-n +i ~li+n+ + n +- l+i i-i t =i-<
=-+ l+ ~-n ,ii i-- :n + i--- ti (SO
3
) ,ii -i- n ti l+i i-i t l=+ +n- (+ n-i
+i i-i- --i t . -z-i- := n-i +i i-i- n = i i - +i l-+i=- ti - + +n- -i- =-+i l-+ ~-n
-i< + n i-- ti -i t ~lil+i +i l+illi +i l---i-=i <lzi - l+i i =+-i t
2H
2
SO
4
SO
3
+ +
H
+
LFkkukUr j . k
~ii i-i+i ~lil+i +i -t =-+i -i+i +i ~lil+i ii -+nii ti -i t
+ SO
3
+

H
r hoz
9. fvn+isa fif+4i
(a) yf+nt+i
-i- n + ti: i - nii +i (l-+n =n t ,ii l--ii- ti -i (l-+ni+i +tni-i t -i- +i ~lil+i
(l-+n tni:i + =ii l-n AlCl
3
+i -l-il- n ti-i t. -i t l+n+i+ ~lil+i +tni-i t (l-+ni+i
~lil+i + ln +- (l-+n tni:
+
o o
X R
,n +i- nii (+ :n+ i- -- ti +i -t ti <lzi- +-i t
l+n +i+ ~lil+i l--- l+illi ,ii =--- ti -i t
(i)
(ii)
(iii) + AlCl
4

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nru n +t a-s+t4 s+fa
n: = ~-ni +i iil-i +i i-i t ~i +n l---i- =i <lzi - l+i i =+-i t
AlCl
3
> FeCl
3
> BF
3
> TiCl
3
> ZnCl
2
> SnCl
4
a<i.2 l---lnli- (l-+n t ni:i +i -i n +- t -i- +i l+n+i+ (l-+ni+i ~lil+i + +n- i-- n
-i<i +i <lzi- +il
(a) CH
3
CH
2
Cl (b) CH
3
CH
2
CH
2
Cl (c) CH
3
CH
2
CH(Cl)CH
3
(d) (CH
3
)
3
CCH
2
Cl (e) (CH
3
)
2
CHCH
2
Cl (f) CH
2
=CHCH
2
Cl
a-i. (a) (lin-i- (b) ~i:=iiln-i- (c) l,l-+ln-i-
(d) --i+l-n-i- (e) --i+ln-i- (f) 3+l-nii-
(b) yutfn+i
-i- +i l+i ~-n +ni i:i i (-ti: i:i + =ii l- n AlCl
3
+i -l-il- n +ii i-i t . -i -i< +
n (l=n -i- i-- ti -i t
f+4iffri
s< 1 : in < n (=ilnn ~i- (acylium ion) i-- ti-i t
R C Cl:
||
O
: :
..
..
+ AlCl
3
, fl y Dy ksj kbM
R C Cl AlCl
3
||
O : :
+
- ..
..
l ad qy
-
AlCl
4
+ [R C = O
..
..
+
R C O:]
+
, fl fy ; e v k; u
s< 2 : l,l- < n (=ilnn ~i- (acyliumion) ,ii -i- n ti l+i i-i t -ii (+ l=ni = + n --i
t
O
||
C
|
R
+
+
O
||
C
R
H
H
fl Xek l ad qy
s< 3 : ~l--n < + ~-- n- l=ni = + n n = (+ i i- +i l-+i=- ti - + +n- -i< + n (l=n -i-
i-- ti -i t
+
-
O
||
C
R
H
H
fl Xekl ad qy
:Cl AlCl
3
..
..
O
||
C
R
, fl y cSUt hu
.
.
.
.
e.g. +
(1) AlCl
3
(2) H O
2
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aia : l+n+i+ (=iln+i ~lil+i =ini-- -l-i=i ( tl--ii- = n+- ti-i t -ii n ~=l+
-i- n n (=iln+i ~lil+i =--- -ti ti-i
e.g.
+ CH COCl
3
AlCl
3
COCH
3
+ HCl
, l hVksfQukWu
10. -ta +t uai
-i- + ~iil+ ii ( ~- lzn iii ,ii t <lzi - t ~i l+ -i- +i ~iil+ = zi C
6
H
6
t ~- := ~iii
t ni-i ni t l+ -i- ,ii ~=--- ~lil+i( <lzi- +i i-i t l= l--- +i + -i ,ii - l+i i
=+-i t
(i) -i- n t ni - nii +i i n l+i i-i t -i -i- nii = - in ~li+-n t ni - nii ~i +i
= i z ti -i t
(ii) -i- +i -+i ti:i-i+i ~lil+i + +n- -i< + n =i:+ni t+= - i-- ti-i t
(iii) -i- +i ~i i - = ~lil+i + +n- i:~i i -i: --i t
(iv) =< ~-ii (in cold) n -i- -iiin - ,ii l+=i +i +i +i : l-l+i -ti ti -i. l+ ~ili+ nn
-i- +i CO
2
( n n li- ti i-i t
(v) = + +izi +i ~- l-il- n . -i- +i t ni - + =ii ~lil+i. l--ii- ~lil+i ti -i t
(vi) tni - ~-ni +i -i- in -ti ti-i t
~- -i +- =ii -i + ~iii tn t l-+i l-+in =+- t l+
(1) -i- n -i- lzii -l-i- t
(2) -i- n -l-i- =ii z ti: i - nii (+ =ni- +l- + ti - t ~- := +ii -i- +i + n (+ ni -i
l--iii -- -i< -ii -i- l,l--iii -- -i< =i t
11. ytai +i aia +t ffri4i
(A) -ta
(1) yutfafna + rnt+i zii
3HC CH

uyh ykSg ~ rIr yky
(2) -ir+ n + f+iifunt+i zii

NaOH
) CaO (
NaOH

+ Na
2
CO
3
(3) n-rua + a-s+t4 fririat+i zii
CH
3
(CH
2
)
4
CH
3
2
K 873 , Pt
H

2
K 873 , Pt
H 3

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(4) -tairyifa4 niir + s4a zii
+ H
3
PO
2
+ H
2
O + N
2
(B) ainra :
(1) fvn +isa fif+4i zii
+ CH
3
Cl
3
AlCl
+ HCl
i n :-
(2) a f+fan fif+4i zii
+ 2Na + CH
3
Br
bZFkj d kq" '
+ 2NaBr
ini-i- in:-
(3) fn-4i fi++ zii
+ CH
3
Br + MgBr
2
(4) n-raa + a-s+t4 fririat+i zii
) H (
Pt , K 873
2


) H 3 (
Pt , K 873
2


nlin=i:+ni t+=- in:-
(C) irnta

3 3
AlCl , X CH
+
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12. -ta +t iui4fa+ fif+4iy
a<i.3 l---lnli- ~lil+i +i i +il
A

4
KMnO
X
a-i.
COOH
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CHEMISTRY
a<i.4 l---lnli- ~lil+i~i n i-- ti- in -i<i + =--i =zi lnli
(a)
Cl
+
3
AlCl
X (b) CH
3
Cl + Y
(c)
3
3 3
3
CH Cl
| |
CH C HC C H
|
CH
+
H C CH CH
3 3

3
AlCl
Z
a-i. X = +l-n=i:+nit+=-
Y =
OCH
3
CH
3
OCH
3
CH
3
~iiinlin inlin(-i=i n
(-i=in
Z =
CH
H CCCH
3 3
H CCH
3
CH
3
CH
3
H C
3
(1 - ~i:=iiln 4 (1, 1, 2 i:nliniln) -i-)
a<i.5 l---lnli- ~lil+i~i n i-- ti- in -i<i +i <lzi- +il
(a) ~ili+ +
3
3 3 3
CH
|
AlCl CH C C H
|
Cl
+
X
~i:=iln+nii:
(b) +
wVsukWy C;
+
1
BF OH CH CH CH C H
3 2 2 2 3

Y
(c)
NO
2
+
Cl
|
AlCl CH CH C H
3 3 3
+
Z
-i:i -i- (~ili+)
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CHEMISTRY
(d) +
3
2 3
3
CH
|
HF CH HC C C H
|
CH
+ =

P
a-i. X = Y = or
Z = +i: ~lil+i -ti P =
CCHCH
3
CH
3
CH
3
CH
3
(1, 1, 2-i:nliniln) -i-
a<i.6 -i- = i:+ l-n (biphenyl) + =znii +i i=il-+ ~lil+i <il
a-i.

3 2
FeBr / Br
Br
A

Cu
13. yfn rnir (ARYLHALIDES) :
(A) yfn rnir +i aia +t ffri4i (Preparationof Aryl Halides) :
1. rniat+i (Halogenation) :
+ X
2

acid Lewis
+ HX
X
2
= Cl
2
, Br
2
n:= ~-n = FeCl
3
, AlCl
3
, ZnCl
2
, Zn :il<
2. l+ii l+=ln+i (Decarboxylation) :

CaO / NaOH
+ CO
2
3. l+-in ,ii (FromPhenol) :
A

5
PCl
+ POCl
3
+ HCl
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CHEMISTRY
(B) l,~il+ -ili+-- ti l--ii- (ArS
N
2) ~lil+i +i l+illi
+ Nu
O
RDS
I Step


II Step
) fast ( X


O
~--i< ,ii n-i -iii ti- t
- =n t i i- n = :n + i - ~-i ~i ~i+li - +- t +ii zi +i +n +- t -ii - ~li+ +iin+
ti i- t t ~izi +i l-i +i+ii- +i -iil <i- +-i t
G :n+i- ~i+ii : +i+ii- -iii. =l+
( (CH
3
)
3
, NO
2
, CN, SO
3
H, COOH, CHO, COR, X)
- =n t i i- n n :n + i- < - t +i +ii- +i ~-iii -i- t ~- ~lil+i +i nl- +n ti i-i t
G :n+i- l-+ii : +i+ii- ~-iii. ~=l+
(NH
2
, OH, OR, R)
aifi+art yifa+ sfaiisa f-4iu
si fifa s
ai fifa s
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CHEMISTRY
iii fifa s
aia l< :n+i- ~i+ii =nt ~iii -ii i l-il- -l-i- t -i t lzii = (inl+ -ili+--ti l--ii-
~lil+i +i =l+ +- t
14. f+ain(ArOH) :
(A) ArOH aia +t ffri4i
(1)
(2)
(3)
(4)
(5)
(6)
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CHEMISTRY
(7)
(B) f+ain + ni
l+-i n nti- l+-ni ai = <ii t . l-+ nn-i + +i ni- 43C, -ii +i-i + +i ni- 182Cti -i t i ( +izi
+i -l-il- n t nnii n n ll- - ti- nn- t t zii-n n n nn = ln l+ =i-< =-+ l+
~-n (nini- ~lil+i) n ziii -i = ln ti - t . l+-i n +i =i-< =-+ l+ ~-n n ln + :=n ni =i ln
-i:i: +i +z < lnnii i-i t -ii lni +i ~i ~li+ -- l+i i-i t -i nin n i-- ti-i t -ii
:=i lni +i ni =iln ti: i +=i: +i i n +i+ -iii l+i i-i t -i nin n -in n n ll- - ti
i-i t
-i +- =ii ni -i ti:l + l+-in i ln+i + ni-ili+ ni t
(C) f+ain +i aia +t ffri4i y iui4fa+ fif+4ii +i uf+iat+i
(1)
(2)
(3) (Major is oxidative cleavage of ring)
(4)

(p-nitroso phenol)
(5)
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CHEMISTRY
(6)
(7)
(8)
(9) (Fries Rearrangement)
(10)
(11) (polymer)
(12)
(13) (14)
(15) (16)
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CHEMISTRY
15. airai-ta
(A) aia +t ffri4i
+
l kUnzH SO
2 4
390K
(B) airai-ta + uii-4 ni
(i) ini -n <ii
(ii) n +i ~ -ii ~li+ i- +- ~- n n ~ln l+ +i l-+ lni+i n ln ti -i t
(iii) +i-i+= 211C
(iv) iziin <ii
(C) airai-ta +t iui4fa+ fif+4iy
(1)
(2)
(3)
(4)
(5)
(6)
(7)
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CHEMISTRY
(8)
(9)
(10)
16. yfanta (ANILINE) :
(A) aia +t ffri4i
(1)
(2)
(3)
(B) yfanta +t iui4fa+ fif+4iy
(1)
(2)
(3)
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CHEMISTRY
(4)
(5)
(6) (Diazotisation)
(7)
(8)
(9)
(10)
(11)
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CHEMISTRY
(12) (oxidation)
(13) C
6
H
5
: C N

=
(14)
17. tairyifa4 niir
(1)
(2)
(3)
(4)
(5)
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CHEMISTRY
(6)
(7)
(8)
(9)
(10)
(11)
(12)
(13)
(14)
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CHEMISTRY
(15)
(16)
(17)
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CHEMISTRY
MISCELLANEOUS SOLVED PROBLEMS (MSPS)
l--- ~lil+i~i +i i +il(
1. (a) + HClO
4
(b) + 2 AgClO
4

Ans. (a) (b) + AgCl
Sol. (inl+ iln+ ti - t -
(i) -l+ (ii) =n-n
(iii) (4n + 2) t-:n+i- i- t l+ n = o , 1,2,3 .......
(iv) (4 n + 2) t-:n+i- + n -l+ ~--i< ti-i t
2. + CH
3
CH
2
CH
2
Cl

3
AlCl
Ans.
Sol. (inl+ i ln+ :n +i---ti l--ii- ~lil+i <- t ~i l< =-i ti . -i +i i-i- +i -l-i= ti-i t
3. (a) +


H
(b) +
(c)
Ans. (a) (b) (c)
Sol. +i l+ +i n +i+ (=in zi- ~lil+i (l-+ni+i +i ~ -ii ~li+ -i nl- = =--- ti -i t
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CHEMISTRY
4. + H
2
SO
4

Ans.
Sol. 2H
2
SO
4
+ +
5.
Sol. +
6.
Ans.
Sol. i:l+-i:n + +ii n (+ n :n+i- <i-i t ~i <=i :n+i-niti ti-i t
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CHEMISTRY
7.

Fe / Br
2
Sol.
8.

Fe / Br
2
Ans.
Sol. :n+i--- ti l--ii- n -iii +iil-n ~i- n-i --i t
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CHEMISTRY
9. (a)

O H / Br
2 2 (b)
Ans. (a) (b)
Sol. (a) n n :n +i- i- c- + +ii ~i- :n+ i---ti + l- l+iziin-i +i c-i t
10. (a)


H / KMnO
4 (b)


H / KMnO
4
Ans. (a) (b)
Sol. (a & b) (i n l+ ti: i +i -i n l< +n = +n (+ -iln+ ti: i - -l-i- ti - ~i+=i+i ti - -i :+
~-n --i t
11. (a)
KOH . aq . 2
CHCl . 1
3

(b)
KOH . aq . 2
CCl . 1
4

(c)
) excess (
O H / Br
2 2

Ans./Sol.
(a) (b) (c) + 3HBr
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CHEMISTRY
13.
4 2
7 2 2
SO H
O Cr Na

Ans.
Sol. +i ln+ (l= = l+-in + ~i+=i+i =ln- i:+ii - --i t i l+ -il+-i- + -in = i-i i-i t

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