"manishkumarphysics.

in"
1
CHEMISTRY
+iifufn+ n i n -4-s-a
sf4 : +ii l+=n =n t i- in i ln+ n = ~-ni ti - t l-t +ii l+=ln+ ~-n +t- t
O
R C O H
d kcksZfDl fy d v Ey
:-+i =ini- = zi C
n
H
2n
O
2
ti -i t .+ii l+=ln+ ~-n -- i ln+ ( = l+in+ =n t i- t l-t =n ~-ni i
-iii n~i- + ,ii +ii l+=ln+ ~-n n ll- - + =+- t n i ~-n -- t (-. (ni:. -i: i:n.
~-n tni: ~i (-ti: i:
O
R C X
v Ey gSYkkbM
O
R C O R'
, LVj
O
R C NH
2
, EkkbM
R C N
ukbVkby
(- ~i (ni: + l- n =ini- = i i- t = ~i:=i (lnn (l= +i + ni ~i n ni + - n n . n il-n
(l= . nil-n ~i t - =i ~- + ni n N, N-i:(lin-n i-in (ni:(DEET) (+ ~-z +i l-+ii + n
i-i i-i t ~i l-l=ln- G (+ (-iii l+ t i (+ li- zi-i: ~iil-+ <i: t
O
O C CH
3
xsj kfuy , fl VsV
xsj kfu; e d k r sy ( )
C
O
N(CH CH )
2 3 2
N, N - - MkbZ, fFky esVkVkWy q, ekbM
H C
3
O
O
PhCH C NH
2
N
S
COOH
CH
3
CH
3
i sfufl fy u G
"manishkumarphysics.in"
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CHEMISTRY
Table-1 : n i n -4-s-ai +i IUPACai+i
"manishkumarphysics.in"
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CHEMISTRY
fz+iifufn+ n
l< l--iii l,-i +ii l+=n =n t t. -i tn l,+ii l+=ln+ ~-n i-- ti - t =
ZvkWbd vEy izksisuMkb
Ey eSyksfud v
COOH HOOCCH
2
vEy Wbd wVsuMkbZvk C;
y lfDlfud vE
COOH CH HOOCCH
2 2
vkWbd vEy gSDlsuMkbZ
vEy fMfid ,
COOH CH CH CH HOOCCH
2 2 2 2
d vEy suMkbZvkWb zkseksisUV
Vsfjd vEy czkseksXyw
c
o
2
Br
|
CHCOOH CH HOOCCH
2 2
vkWbd vEy isUVsuMkbZ MkbZesfFky
Ey XywVsfjd v MkbZesfFky

| |
3 , 3
,
3
2 2
3
CH
|
COOH CCH HOOCCH
|
CH
vkWbd vEy isUVsuMkbZ s MkbZDyksjk
vEy sXywVsfjd MkbZDyksjk

o o
4 , 2
,
Cl Cl
| |
CHCOOH HOOCCHCH
2
"manishkumarphysics.in"
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CHEMISTRY
n i n-4-s-a + iifa+ ni :
(1) in -i- =<- nti- -in i in < t ~in + -i- =<- ii nti- ni ni in -ni < t --- =<-
(>7) ii nti- ni n + =ni- ai= t
(2) iai+ f-< :- +ii l+=ln+ ~-ni +i +i-i + (-+i t n. +ii -i i (l-ti:i = i<i ti -i t (i =ni- ~il+
ii in ti - t )
CH C OH
,
bp 118C
3
, fl fVd v Ey
O
CH OH
1-
bp 97C
3
i zksi sukWYk
CH CH
2 2
+ii l+=ln+ ~-ni +i --- +i-i + -iii l,n+ ti: i - -i- + liin- ti -i t
R C
C R
O ----- H O
O H ----- O
gkbMkst u cfU/kr vEy h; f} y d
+ii l+=n+ ~-n +i --+ = n- ~i ii in (-+i ti n +i - n-i n ~li+ ti -i t +i l+
(i) =n t +i -l-il- + +ii OH-i (-+i tin +i - n-i n +ii l+=n+ ~-n n ~li+ i i t
(ii) +ii l+=n+ ~-n <i H--i ,ii ~i= n t- t
(- ~i ~-n +ni i:i +i +i-i + l-< =ni- ~il+ ii i- in ~ziili- (-+ - + nnin =ni- ti -i t
-i: i:ni +i +i-i + =ni- ~il+ ii i- in (-i ~i ~-n +ni i:i = i<i ti -i t t ii =ni-i
=i-i =nti + n n l,i i =i- + liin- ti -i t
R C N :
+ +
+
+ : N C R
(-i:i:ni +i l,ii =i-)
t ~-n -- --- i i +ii l-n =n t i- t . n l+- +ii l-n =n t +i i i-i +i-i + l-< t - +n ii
in-i t
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CHEMISTRY
(3) nnai+ f-< : ~-n i 8 = i<i +i - i- t =ini-- +ai ti - t . :=+ ~l-l+- t l, i - i- ti n-i
ini n l, i +i -l-il- -ii: l+-n in+ = zn ii n iii --- +-i t l=+ liin- +i-i + l-<
+n ti -i t
O
CH (CH ) C OH
3 2 16
LVh; fj d v Ey , mp 70C
O
C = C
C = C
H
H H H
CH (CH )
3 2 4
CH
2
(CH ) C OH
2 7
ln-iln+ ~-n mp 5C
+iifufn+ n +i nnai+ : ~-ni + nn-i +i +i +i : l-ln- +n -ti t (10 +i - nii -+) l- ~-ni n
+i - nii =n = i n ti - t --+ nn-i + --- -ii lin = i n +i - nii i- in ~-ni + nn-i + l-<
l--- ti - t :=+i +ii t t l+ +ii l+=ln+ ~-n =n t ~i n lin =n t =n = i in ~-n n li- l<zii n
ti - t -ii +i- ini ln n (Zig-Zag) n ti -i t. l== l+-n in+ n ~-zi -t l+ (fit) ti i-
t . liin - nn-i + --- ti i- t :=+ li- ii -i t lin = i n +i - nii i- in +ii l+=ln+
~-ni n
(ni:i +i +i-i + ~i nn-i + =ni- ~il+ ii i- in ~- i ln+i +i - n-i n ~li+ ti -i t iiln+ ~i
l,-i+ (ni: n ti: i - i- n iin n - t
C
R
N
R'
R'
:O:
. .
C
R
N
R'
R'
:O:
+
. .

C = N
C = N
O
R
R
H
H
H
H
+
+

.
.
.
O
O
. . .
C
R
N H
+
H
ti:i- i-

R'
N
R'
C
R
O
+
+

+ O
C
R
N
R'
R'
+
~--~iil+ ~i+i i
iiln+ ~i l,-i+ (ni:= + n n ti:i- i- + liin - --- nn-i + l-< <lzi- +- t
O
H C N
CH
3
CH
3
MkbZesfFky QksekZekbM
(DMF) mp 61C
O
CH C N
3
H
CH
3
N-
m.p. 28C
esfFky , fl VkekbM
O
CH CN
3
CH
2
H
H
i zkssfi ; ksukekbM
mp 79C
(4) fn4ai +ii l+=ln+ ~-n n + =ii ti: i - -i -i- t ~i +n ~il+ ii (4 +i - nii = +n) in
+ii l+=ln+ ~-n n + =ii lnl- ti - t
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CHEMISTRY
~-n -- ((-, ~-n +-iii:. (-ti:i:. -i:i:n ~i (ni:) =ini- +il-+ lni+i n ln ti-
t = (-+i tn. : i. +ni i -i+ - (-+ - ~i ( i n l+ ti: i+i - ~-n +ni i: ~i (-ti: i: +i -ili+-- ti
lni+i (= H
2
O ~i (-+itn) n -in -ti l+i i =+-i t +il+ t :- lni+i + =ii ~lil+i
+ n- t
+iifufn+ ni +i aia +t ffri4i
1. fn-4i fi++ + +iifunt+i + zii +iifufn+ ni +i uznii
RMgX + O = C = O
bZFkj
d kq" '

OMgX C R
||
O

X ) OH ( Mg
O H / H
2

+
OH C R
||
O

MkbZ, fFky bZFkj
RCOMgX
||
O
: :
..
..
gSy kseSXuhf' k; e
d kcksZfDl y sV
RCOH
||
O
: :
..
..
d kcksZfDl fy d
v Ey
Vsu w DyksjksC; 2
Cl
|
CH CHCH CH
3 2 3
1. Mg / MkbZ, fFky bZFkj
2. CO
2
3. H O
3
+
%) 86 76 (
2
H CO
|
CH CHCH CH
2
3 2 3

y VsukWbd vE q esfFkyC;
Br
CH
3
9- -10- czkseks eSfFky fQuSFkzhu
1. Mg / MkbZ, fFky bZFkj
2. CO
2
3. H O
3
+
CO H
2
CH
3
10- -9-
(82%)
esfFky fQuSUFkzhu
d kcksZfDl fy d v Ey
a<i.
3
3
CH
|
MgBr CH CH
+

H / O H ) ii (
CO ) i (
2
2
) 2 (
CH
|
COOH CH CH
3
3
y isuksbd vE esfFkyizks VkbfjdvEy w vkblksC;

a<i. C
3
H
5
Cl (=---) (A)

dryether / Mg
(B)
+

H / O H ) ii (
CO ) i (
2
2
(C)

3
] O [
C
8
H
12
(D)
"manishkumarphysics.in"
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CHEMISTRY
Table -2 : +iifufn+ n + iifa+ ni
IUPAC -in =ini- -in = zi nn-i + +i-i + ln-i
l-< l-< (g/100 g H
2
O)
(C) (C)
ni-i :+ +iln+ HCOOH 8 101 (lnl-)
:i -i :+ (l=l+ CH
3
COOH 17 118
i -i :+ il-i :+ CH
3
CH
2
COOH 21 141
2-il-i :+ (+i:ln+ H
2
C=CHCOOH 14 141
-i :+ i:l+ CH
3
(CH
2
)
2
COOH 6 163
2-nlini-i:+ ~i:=ii:l+ (CH
3
)
2
CHCOOH 46 155 23
l-i-2-l-i:+ +i i l-+ CH
3
CH=CHCOOH 71 185 8.6
- -i :+ nl+ CH
3
(CH
2
)
3
COOH 34 186 3.7
3-nlin-i :+ ~i:=inl+ (CH
3
)
2
CHCH
2
COOH 29 177 5
2,2-i:nlini-i:+ i:ln+ (CH
3
)
2
CCOOH 35 164 2.5
t+=-i :+ +~i :+ CH
3
(CH
2
)
4
COOH 4 206 1.0
~i+-i:+ + ni:+ CH
3
(CH
2
)
6
COOH 16 240 0.7
+i-i :+ +l+ CH
3
(CH
2
)
8
COOH 31 269 0.2
Table -3 : n -4-s-ai + iifa+ ni
4ifn+ ai nnai+ (C) iai+ (C) n
f-< f-< fn4ai
CH
3
COCl :i-i n+nii:
(CH
3
CO)
2
O :i -i :+(-ti: i:
CH
3
COOH :i -i :+ 17 118
CH
3
CONH
2
:i -ini: 222
CH COCH CH
3 2 3
O
(lin(l= 83 77 10%
HCN(CH )
3 2
O
i:nlin+inini: (DMF) 61 153 lnl-
CH CN(CH )
3 3 2
O
i:nlin(l=ini: (DMA) 20 165 lnl-
CH
3
C N (l=i -i: i:n 45 82 lnl-
"manishkumarphysics.in"
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CHEMISTRY
Ans. (A) = ; (B) = ;
(C) = ; (D) =
2. airairni + nsiaa + zii +iifufn+ ni +i uznii
f+4iffri
RC N
ukbVkby
+
2H O
2
t y
+ H
+

heat
RCOH
||
O
d kcksZfDl fy d
v Ey
+ NH
4
+
v eksfu; e
v k; u
=i-i: +i ni ~i- (~-n -l-) :
Ex.
CH Cl
2
cSfUt y Dy ksj kbM
DMSO
NaCN
CH CN
2
cSfUt y l k; ukbM(92%)
H O,
H SO
2
2 4
xeZ
CH COH
2
Qsfuy , fl fVd vEy (77%)
||
O
Ex.
CH CCH CH CH
3 2 2 3
||
O
2-i sUVsukWu
CH CCH CH CH
3 2 2 3
|
OH
|
CN
H O, HCl
2
xeZ
CH CCH CH CH
3 2 2 3
|
OH
|
CO H
2
2- -2-
(2- 60%)
gkbMkWDl h esfFky i sUVsukWbd v Ey
i sUVsukWu l s
-<i.. (i-in = i-i:+ ~-n l--- +i -ii i-i t
CH
3
CH
2
OH

5
PCl
CH
3
CH
2
Cl

KCN
CH
3
CH
2
CN

+
H / O H
2 CH
3
CH
2
COOH
-<i.. C
3
H
6
Cl
2
(A)
KCN
(B)

+
OH / O H
2
(C)
2
CO
A

2-nlini-i:+ ~-n
Cl
|
CH C CH
|
Cl
3 3

KCN
CN
|
CH C CH
|
CN
3 3

+
OH / O H
2
COOH
|
CH C CH
|
COOH
3 3
2
CO
A

2-nlini-i:+ ~-n
aia : 1. (l-+n =i-i: -i- + ln (l-+n tni:i +i l+i (-+itiln+ KCN i of NaCN = +i: i-i t
R Cl + KCN
. Alc
R C N + KCl
"manishkumarphysics.in"
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CHEMISTRY
2. := ~lil+i +i -i n ii n ~ii ti +- n l+i i-i t := +i (l-+n t ni:i n (+ +i - nii +i lz
ti i-i t (l-+n+ni i:i +i (-+i tin -ii PX
5
+i l+i = i-- l+i i-i t
ROH + PX
5
R X + POX
3
+ HX
3. (l-+n =i-i:i +i n ~i- ~lil+i (+ -i ni ~lil+i t l=n (l-+n t ni: ~i (-+i ti n n (+ +i -
+i lz +i i-i t
3. yf+nta + iut+i + ziiyifa+ n a-s-a ria r+
|
CH
3
VkWy wbu
O H / H ) ii (
OH / KMnO
2
4
+

|
COOH
cSUt ksbd v Ey
O H / H ) ii (
OH / KMnO ) i (
2
4
+

|
CH CH
2 3
, fFky cSUt hu
Ex.
||
CH
3
CH + 6[O]
3
P-t kbfy u
4 2
7 2 2
SO H
O Cr K

iui4fa+ fif+4i
1. nt4 ui4 :
+iifun+ n +t nt4ai:-
R C OH
O
-
R C O
O
(I)
+

H
(i)
-
R C O
O
(I) <i ~--i<i =--i (A) ~i (B) n ~l-- i-i t
t ~i- ~--i< -iii ~i ~--i<i =+ =--i (C) t
-
R C
O
O
I(A)
-
R C
O
O
I(B)
R C
O
O
I(C)
(ii)
-
R C O
O
~i- ~- -i< + +ii ~li+ -iii t :=ln( +ii l+=n+ ~-n ~-ni + l- +i ti -i t
(iii) :n + i- ~i+ ii =n t (I ii) (-i- +i -iil +- t ~i :=ln( ~-ni +l- n l, ti -i t
C
O
O
X
Ex. F CH
2
COOH > Cl CH
2
COOH > Br CH
2
COOH > I CH
2
COOH
Ex. Cl C COOH
Cl
Cl
> Cl CH COOH
Cl
> Cl CH
2
COOH > CH
3
COOH
"manishkumarphysics.in"
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CHEMISTRY
(iv) :n +i- l-+ii =n t (+I ii) (-i- + -iil n +ni +-i t :=ln( ~-ni =in n +ni ti-i t
C
O
O
X
Ex. HCOOH > CH
3
COOH > CH
3
CH
2
COOH
Ex.
COOH
COOH
>
COOH
COOH
CH
2 >
CH
2
COOH
CH
2
COOH
Ex. -n-in+ ~-ni =i-i:-
RCOOH > HOH > ROH > HC

CH > NH
3
> RH
-i ~-n +i ~-ni-i =ln- -ii + -iil + ~iii -n-i +i i-i t
2. fif+4i fa OHur u siaia +i fa+iua riai r
(i) atn fnau + uii fif+4i : =ii +ii l+=ln+ ~-n -in lnn= +i nin n ll- - + < - t
(ii) riia + uii fif+4i :
2 CH
3
COOH + 2Na + H
2
2CH
3
COOH + Zn + H
2
(iii) yf+nt + uii fif+4i :
CH
3
COOH + NaOH CH
3
COONa + H
2
O
(iv) +iiaa i ir+iiaa + uii fif+4i :
2CH
3
COOH + Na
2
CO
3
2CH
3
COONa + CO
2
+ H
2
O
CH
3
COOH + NaHCO
3
CH
3
COONa + CO
2
+ H
2
O
+ii l+=ln+ ~-n +i =i ln +ii - ln- + =ii ~lil+i : =i < <it -i< +-i t l+ +i-in
t ~lil+i -ti <zii - t :=ln( := ~lil+i +i -i n +ii l+=ln+ ~-n ~i +i-in +i li l<- +- n l+i
i-i t
(v) fn-4i fi++ + uii fif+4i :
RCH
2
MgBr + R'COOH RCH
3
+ R'COOMgBr
Note: (+ n ~-n < n ~-n + -=+ ni = l-iil- + <-i t
Ex. CH
3
COOH(Stronger acid) + CH
3
ONa CH
3
COONa + CH
3
OH(Weaker Acid)
Ex. CH
3
COOH (stronger acid) + NaHCO
3
CH
3
COONa + H
2
CO
3
(Weaker acid) H
2
O+ CO
2
|
(+ii l+=ln+ ~-n +i i nziini i-ii)
3. OHur +i sfaiista +a int fif+4i
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CHEMISTRY
(i) n niir +i faii :
Ex. + SOCl
2
+ SO
2
+ HCl
Ex. + PCl
5
+ POCl
3
+ HCl
(ii) f+zi yat+i
+ii l+=n+ ~-n (-+i tin + =ii = i-- ~lil+i + ,ii (- <- t t ~lil+i (-i+i +tni-i t
uii-4 fif+4i :
+ R' OH + H
2
O
ffzia a<iri :
+ CH
3
CH
2
OH
+ CH
3
OH
f+4iffri : (n a-sfa yat+i)
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CHEMISTRY
l< := ~lil+i +i ~n ~lil+i +i -ii +- t . -i t ~-n +i ~-n - l- (-i+i +i l+illi t l+
z- ~lil+i +i -ii +- t . -i t (- +i ~-n - l- n ~i- +i l+illi t ~-n - l- (-i n
~i-
liin tnii --i n: l-il- l-i +-i t l< tn ~-n +i (-i+i +-i -it- t. -i tn (-+itin +i
~ili+ n - t ~i n + -- =n -= tii i-i t l< tn (- +i ~i- +i-i -it- t -i. tn n
+i ~ili+ nn -il+ tn -- ni HCl i -- ni H
2
SO
4
+ =ii (- +i l+n+= (refulx) + =+
(iii) yir +i faii :
i-- n +ii l+=n+ ~-n ~i (ni- = (ni: +i = zn ii -ti l+i i =+-i -+ l+ ~ni l-n ni +i n
= nn - l+i i( (ni: + = zn ii + ln( t ~-zi lli -ti t
(iv) n yaririr +i faii :
4. f+iiunt+i fif+4i :
(i) uiinir f+iiunt+i :
uii-4 fif+4i :
:= ~lil+i n +i(-i- n-i --i t
~lil+i +i < +i (-i- + -iil l-i +-i t
RCOOH :n + i- ~i+ii =n t l+ii +=ini+i < +i -i- t
Ex.
=iini:n l+ii+=ni+i +i < I > II > III > IV > V
"manishkumarphysics.in"
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CHEMISTRY
Ex.
l+ii+=ni+i +i < I > II > III > IV
(ii) (a) |-+tai +iifufn+ n +i f+iifunt+i :
~-n l-n +iil-n =nt -l-i- ti-i t +iil+=ln+ ~-n =nt = (+ +i- l-+n i-i t.
|-+ii ~-n +tni-i t. --+i 100150Cnn l+i i-i t . -i -<i = l+ii l+=ni+ - ti i- t
l+ii l+=ni+i <i l-il- n ti -i t
~-n - l+ii l+=ln+ - ti -i t t 6 =<-i -+i = +ni ~-ii + ,ii ti -i t
t ~lil+i =ii ti :-in -i-i t. (-il-+ n-i -ti --i t t :-in n lin +ii- n -nii+- ti i-i
t
+ii l+=n (-i- l+iil+=ni+- ti-i t t ~- -i<i -iii+- :-in (-i- -i-i t
(ni+l+ i l+ =+n-i+ l+iil+=ni+i <zii- t. o i | l-il- llzi l+in+ =nt i l,-i i
lzi-i i- t
"manishkumarphysics.in"
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CHEMISTRY
(iii) +i ua siaa
2RCOOK + 2HOH
is Electrolys
R R + 2CO
2
+ H
2
+ 2KOH
f+4iffri
R CO
2
K R CO
2

+ K
+
yai s : - R CO
2

R
-
2
CO + e

(~i +=i+i)
(I)
R
-
2
CO

-
R + CO
2
(II)
-
R +
-
R
R R
+ii l+=ln+ ~-n + ni n l< +i- nii +i = i n t . -i i-- (-+ - n 2(n1) +i- nii ti - t
Ex. 2CH
3
COOK + 2H
2
O
is Electrolys
CH
3
CH
3
+ 2CO
2
+ H
2
+ 2KOH.
(iv) r-ut+ fif+4i (iif+iifun+i) :
RCOOAg + Br
2
RBr + CO
2
+ AgBr
f+4iffri :
Step 1 : R.COOAg + X
2
+AgX
Step 2 :
Step 3 :
Step 4 :
i ni- ~li+ -i n t ni - t n l+- +ni i- ~i ~ii i- ii -i n n ln i- t ~ii i- ~li+n + +
n ti-i t. ~li+n + + i- ~- i- n ti -i t -i< + l-ii i n
A ~ii i- ni +i ~- i- 1 : 1 t . -i (l-+n t ni: i-- ti -i t . Al< ni +i ~- i- 2 : 1 t . -i (- RCOOR
i-- ti -i t := =ini-i ~lil+i +t- t := +ii l+=n+ (- + = znii n -i n l+i i-i t
5. HVZReaction(Halogenationof aliphatic acids andSubstitutedacids)
HVZfif+4i (yfn+fa+ n i sfaiifsa ni +i riiat+i)
+i -+i = +i t - +n nizii +i -l-il- n . ( ln+ l+ +ii l+=ln+ ~-n +ni i- i i ni- + =ii ~i=i-i = ~lil+i
+ i ln+ +i nli i-- ti-i t l=n -l-i- o-ti: i - t -ii - ,ii l-iil- ti-i t t t n i -ti ln -+i
~lil+i t :=+i --in+ + l- + +i l=n + n ~-+i t ni -i+i ti -i t . -ii t --i l=n t l+i
ti -i t. t ~lil+i ~-- = zn iiin+ -in +i t
CH
3
COOH

P , Cl
2
ClCH
2
COOH
P , Cl
2
Cl
2
CHCOOH

P , Cl
2
Cl
3
CCOOH
:- t ni -i+ - ~-ni + t ni - -ili+-- ti l--ii- ~i lni - ~lil+i n := +i i- t = l+ =n (l-+n
t ni: = n ti -i t t ni -i+i. +ii l+=ln+ ~-n = ~- ~iz+ l--iil- +ii l+=ln+ ~-ni n l- - +-
+i in < ti -i t
acid
enated log ha An
Br
|
RCHCOOH
o
+ large excess of NH
3

acid o min a An
NH
|
RCHCOOH
2
o
Br
|
NaOH RCHCOOH +
OH
|
RCHCOONa

+
H
acid hydroxy An
OH
|
RCHCOOH
o
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CHEMISTRY
Br
|
) alc ( KOH CHCOOH RCH
2
+
RCH = CHCOO

+
H
acid d unsaturate , An
CHCOOH RCH
| o
=
Ex. CH
3
CH
2
COOH

P / ) eqV 1 ( Br
2 (A)

KCN
(B)

A
+
/ H / O H
2 (C)
(A)
Br
|
COOH CH CH
3
; (B)
CN
|
COOH CH CH
3
; (C) CH
3
CH
2
COOH
Summary of reactions of carboxylic acids :
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CHEMISTRY
+iifufn+ n -4-sa (Carboxylic Acid Derivatives)
+ii l+=ln+ ~-n = l-+-n =-l-i- ~i ~i (+ < = + =il-+ =n +iifufn+ + f+4i-+ -4-s-a
+tni- t : ~-n +nii:. (-ti:i:. (ni: ~i (- t iln+ t -- t l-n +ii+=ln+ =nt +i
OH =nt, CI,OOCR, NH
2
, i OR` ,ii l--iil- t-i t
~-n +ni i: (-ti: i: (ni: (-
=ii (l=n =nt i- t
~-n + =ni- l== =-l-i- t . ~-n -- (ln+ l+ i (i n l+. l--iii i ~ l--iii ti =+- t -it zi i
zi i ~-n +i = --i + z ii ti l+in+ =n t + n i =ni- ti - -ilt(
n -4-s-a +t ni+ifi+ if+4i (aifi+art yfun sfaiisa) : :
-ili+--ti (l=n l--ii- inin+ lni- l+illi ,ii ti -i t ~i- ini -ili+-- ti +i +ii l-n i n ti -
= --+n+i +i- + =ii i l--iii n-i --i t

t -- +n+i n-i -iii -ti ti -i t ~i := i++- -ti l+i i =+-i t
~i +=i- + ~i-ii :n + i - n p -i -i- t . ~i ~i :=+ -ii :n + i- + =ii lni l- ti - t < n
-ii tn l-+il=- ti -i t . +i l+ < n -ii (+ ~-zi l-+il=- =n t ti -i t
l< ~i- ini -ili+-- ti n-ii t -i +ii l+=ln+ =n t -- -ili+-- ti (l=n l--ii- ~lil+i < - t l<
~i- ini -ili+-- ti ~i l+i+i+ n (l=n =n t = t ( =n t +i -ii+-i =ni- t -i --+n+i n-i =
+i : ii =n t =ni- < = l-+n =+-i t ~i liin + n l+i++ ~i l--iil- -i< +i lni i-- ti -i
t
(i)
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CHEMISTRY
(ii)
(iii)
(iv)
(v)
yfun aifi+art sfaiisa fif+4i + fny zia :
(i) L +i - n-i n ~-zi l-+il=- =n t ti -i -ilt(. ~ii - Nu +i -ii+-i +i -n-i n ~li+ ti -i -ilt(
(ii) RCOL ~i+ni + ln( i-- n -ili+-- ti ti -i -ilt(
(iii) + =ii ~lil+i +- + ln( +ii l-n +i- i-- :n +i---ti ti -i -ilt(
(A) n rnir
yfun rnir aia + ffri
(i) RCOOH + PCl
5

RCOCl + POCl
3
+ HCl
(ii) 3RCOOH+ PCl
3
3RCOCl + H
3
PO
3
(iii) RCOOH + SOCl
2

Pyridine
RCOCl + SO
2
+ HCl
Ex. 3CH
3
COONa + PCl
3
Distil
DyksjkbM flVhy ,
3 3 3
PO Na COCl CH 3 +
Ex.
V csUtks, e lksfM;
3 5 6
POCl COONa H C 2 +

Distil
DyksjkbM csUtkby
3 5 6
NaPO NaCl COCl H C 2 + +
iui4fa+ fif+4i
(1) +iifun+ n + uii fif+4i
+ii l+=n+ ~-n ~i (l=n +ni i: +i ~lil+i = ~-n (-ti: i: i-- ti -i t t ~lil+i l-ni i + -< < z
= +i i-i t . - < n +i l-+ -ii = lli- +i lnnii i-i t lli- := ~lil+i + ln( - + -ii ti: i -
+ni i: +i -<i=i- +- + ln( -ii +i -t +i +-i t
+ +
+
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(2) y+irin + uii fif+4i
(l=n +ni i: (-+i tin + =ii ~lil+i ++ (- -i-i t t ~lil+i lli- +i -l-il- n +i i-i t
+ +
+
(3) ifa4i i yta + uii fif+4i
+ + + +
(4) n siaa
(l=n +ni i: n + =ii ~lil+i ++ +ii l+=ln+ ~-n < - t -ii n . ~-n :=+ +ii l+=n ni n ll- -
ti i-i t := ~lil+i +i = zn ii n t - +n i n<i- t +i l+ (l=n +ni i: +ii l+=ln+ ~-n ,ii = zn li-
ti -i t ~-iii :=+i ll-
+ +
+ +
(5) n rnir +t +iriif-+ + uii fif+4i
(a) ln -i ~li+n + + =ii
(b) lnni- ~li+n + + =ii
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CHEMISTRY
(6) n rnir +i s4a
(a) LiAIH
4
+ ,ii ~--
(b) H
2
/Pd / BaSO
4
+ =ii ~-- (i-n ~--)
Summary of reactions of acid halide
(B) n yir
n yir aia + ffri
1. ya +t ifa4i i yfa + uii fif+4i
Ex. + +
~nil-i n +i -n-i n ~li+ -ili+-- ti t t ~lil+i ni ~ni l-i +i -i n ++ = i t
Ex. + +
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CHEMISTRY
(ln-. i l+ ~ni l-i +i l--iii --. =ni- n l+i +- t :
Ex. + +
Ex. + +
Ex. + +
Ex. + +
2. ~-n t ni: =
RCOCl + 2NH
3
RCONH
2
+ NH
4
Cl
3. (-ti:i: =
(RCO)
2
O+ 2NH
3
RCONH
2
+ RCOONH
4
4. (- =
RCOOR' + NH
3
RCONH
2
+ R'OH
5. +ii l+=ln+ ~-n + ~ni l-n ni =
RCOONH
4
A
RCONH
2
+ H
2
O
acetate . Amm
4 3
COONH CH
A
Acetamide
2 3
CONH CH
6. =i-i: =
R C N + H
2
O
NaOH O H or
HCl . Conc
2 2

R CONH
2
O H N C CH
2 3
+
4 2
SO H . Conc
2 3
CONH CH
7. +
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CHEMISTRY
iui4fa+ fif+4i
1. ri+ia saf-4iu
ti+ni- - l-i= n ~ l--iii (ni: =i ln ti: i+=i: ~i i ni- + =ii ~lil+i ++ iiln+ (ni- < -i t
l=n (ni: +i - n-i n (+ +i- +n ti-i t
uii-4 fif+4i
+ NaOH + Br
2
R N = C = O R NH
2
~i:=i=i-
f+4iffri :

O
OH
CO
2
|+R
O
NH
R NH
2
(2) yir +i n siaa
+ +
~-n n. l+ (ni- ii-i+- t. ~nil-n ~i- R
2
' <-i t
+ +
-ii n . +ii l+=ln+ ~-n l i i -i+ - t . +ii l+=n ~i- < -i t
+ +
~-n-ii ~lil+i i l+ (ni: -i + - + i< ti -i t . i n~i- ~lil+i +i ~--+nii -i < -i t
<i-i l-il- n ~-n n (ni- -i< ii -i+- ti -i t. +ii l+=n+ ~-n -ii n lii -i+- ti -i t
Ex.
A

4 2 2
SO H / O H
+
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CHEMISTRY
Ex. +
Ex. (A) C
3
H
7
NO+i = --i <il( l=+i ~-ni n ~i- +- ~-n (B) ~i (ni- (C) i-- ti -i t ~-n (B)
(+)ve - <i i-ii <-i t
Ans. A = or
Summary of reaction of amide:
Ex.
Ans.
O
||
NH C CH CH
2 2 3

(C) ya
aia +t ffri
(i)
lhfVd vEy ,
OH H C COOH CH
5 2 3
+

+
H
O H H COOC CH
2 5 2 3
+
OH CH COOH H C
3 5 6
+

+
H
benzoate Methyl
O H COOCH H C
2 3 5 6
+
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CHEMISTRY
(ii) CH
3
COCl + C
2
H
5
OH
Pyridine
CH
3
COOC
2
H
5
+ HCl
(-+i ti n (l=n +ni i: + =ii -ili+-- ti (l=n l--ii- + ,ii (- < -i t t ~lil+i < n -ii = lli-
+i -l-il- n ti-i t
+ + +
Ex. +
Ex. C
6
H
5
COCl + CH
3
CH
2
OH
NaOH
C
6
H
5
COOCH
2
CH
3
+ HCl
iui4fa+ fif+4i
1. ya +i n a-sfa n siaa (A
Ac
2):
H
2
O-ii ROHnnin =ni- -ii+-i i- t ~- -- + +n+i n-i -I + =ii ++i + (- +i l-ni i +-i
t -ii -- ++i n-i -II + ++ + =ii +ii l+=ln+ ~-n -i-i t -=i =n ~lil+i =i- t --i t
-i (- ~i +ii l+=ln+ ~-n <i -i i-- ti - t
CH
3
COOH + ROH
n +i ~ili+ n - =i- <i i -+ lzi+ ti i-i t
CH
3
COOH + ROH
f+4iffri :
2. ya +i +iia-sfa nsiaa {uiat+i) (B
Ac
2):
(- +i -i + n ~-ni n ~i- ti -i t . -ii - l- n ~i- < -i t -ii - l- n ~i- =i -i+i
+tni-i t . =i n l- zi< t (- +i ni NaOH + =ii nn +- (Reflux +- ) ~-n +i =i ln ni
-ii (-+i tin i-- ti -i t :
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CHEMISTRY
+ii l+=n ~i- -ili+-- ti l--ii- + l- ~l+iziin ti -i t +i l+ t +ii lzi- ti -i t (- + -ii l-
n~i- (+ ~iz+ ~--+nii ~lil+i t (- + -ii l- n~i- +i l+illi n (l=n +i-
-ili+-- ti inin+ lni - iin n -i t
f+4iffri :
=n-iil-+ ~ l+- (- + ~- = := l+illi +i nii i-- ti -i t (lin i -i ( +i (- + : i +i
+ ~i+=i- +i
18
O+ =ii ~ l+- l+i i-i t . +i ni NaOH+ =ii n ~il- +i- --- (i -in n
=ii
18
O <lzi - ti - t
l< ti: i +=i: ~i- (l=n +i - + -ii- (l-+n +i - ~i+ni +-i t . (-+i ti n ~ l+- -ti ti -i t (l-+n
+i - ~i+ni nnin l-i- -ti ti -i t
l +ii l+=ln+ ~-n + (- + =ii -ili+-- ti ~i+ni -l-i- (l-+n +i - ti -i t t =-+i l-+ ~-n
(i=i:n ~i ln=i:n ) + (- + =ii ~i+ni +i iiln+ -i+i t
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CHEMISTRY
Summary of reaction of esters :
(D) n yaririr
n yaririr aia +t ffri
1. +iifufn+ n u
Ex.
vEy flfVd ,
3 3
HOOCCH COOH CH +
A ,
5 2
O P
kbM ugkbM , lhfVd ,
O H CH . CO . O . CO CH
2 3 3
+
Ex.
A ,
5 2
O P
Ex.
A ,
5 2
O P
Ex.
A ,
5 2
O P
+
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CHEMISTRY
Ex.
A ,
5 2
O P
i- z =<- -+i (-ti:i: -ii: ti - t
2. n i n rnir u
Ex. CH
3
COOH+ CH
3
COCl
Pyridine
CH
3
CO.O.COCH
3
+ HCl
Ex. CH
3
COCl + CH
3
COONa
A
CH
3
CO.O.COCH
3
+ NaCl
iui4fa+ fif+4i
(1) yifa+ 4ifn+ + uii fif+4i (vtn+isa yfunt+i )
Ex. + ArH +
Ex. + +
Ex. A , B , C , D ~i E +i t-i-i
~-n (A)
A
B
3
AlCl / Mesitylene
Sol. (A) = CH
3
COOH; (B) =
O O
|| ||
CH C O C CH
3 3 ;
(C) = (D) =
(2) y+irin + uii fif+4i
~-n (-ti: i: (-+i tin + =ii ~lil+i ++ (- -i- t t ~lil+i lli- +i -l-il- n i ~-n ,ii
-l- ti-i t l< n -<iti n (l=l+ (-ti:i: +i +n (+ (l=n =nt (- -i- n =-nln- ti-i t
l+ <=i =nt (l=l+ ~-n +i (l=n =nt - i-i t
Ex. + +
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CHEMISTRY
Ex. + + CH
3
COOH
(3) ifa4i i yta + uii fif+4i
~-n (-ti: i: ~ni l-i ~i (ni- + =ii ~lil+i ++ (ni: -i- t (ni- + <i ni n - -i + +i ~iz+-i
ti -i t l< n -<iti n (l=l+ (-ti: i: +i + n (+ (l=n =n t (ni: -i- n =-nln- ti -i t . l+ < =i
(l=n =nt (l=l+ ~-n +i (ni- ni -i-i t
+ +
+ + CH
3
COOH
(4) nsiaa
~-n (-ti: i: n + =ii ~lil+i ++ <i +ii l+=ln+ ~-n < - t -+i (-ti: i: l,+ii l+=ln+ ~-n < - t
+ +
+
7. ais +i s ii :
(a) iai+iifufn+ n s ais +i sii
2R COOH
(b) fz+iifufn+ n s ais +i sii
CH
3
COOH
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CHEMISTRY
(c) ririut n s ais +i sii
(1) o ti : i +=i ~-n
(2) ririut n
(3) | ririut n
4 i 8=<-in ~-iii ti -i t :=ln( |-ti: i +=i ~-n +i nn +- o, | ~= - -- +ii l+=ni+ ~-n i-- ti -i
t
(4) o ririut n
(e) ya s ais +i sii
R` COOH to R` CH = CH
2
Mech : R` CH = CH
2
+ R COOH
~lil+i l=- lni - ti-i t ~i ti+ni- -i< -i-i t
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MISCELLANEOUS SOLVED PROBLEMS (MSPS)
1. Select the correct statement about the following compounds I, II, III.
iln+ I, II, III = = li- =ti +i- +i -- +il
(A*) (I) decarboxylates faster than (II) on heating.
(B) Only *CO
2
is eliminated on heating of compound (I).
(C) Compound (I) eliminates a mixture of CO
2
and *CO
2
on heating.
(D) The rate of decarboxylation of (II) is faster than (III).
(A*) nn +- i ln+ (I) i ln+ (II) +i ~ -ii -i -i = l+ii l+=ni+ - ti -i t
(B) iln+ (I) +i nn +- + n *CO
2
l-+ili- ti -i t
(C) i ln+ (I) nn +- CO
2
~i *CO
2
+i lni l-+il=- ti -i t
(D) i ln+ (II) + l+ii l+=ni+i +i < i ln+ (III) = -i ti -i t
Sol.
No decarboxylation CO
2
CO
2
rate of decarboxylation : III > I > II.
CO
2
l+ii+=ni+i +i < : III >I >II.
2. final product is
~l-n -i< t
(A) (B*) (C) (D)
Sol.
3. final product is
~l-n -i< t
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CHEMISTRY
(A) (B*) (C) (D)
Sol.
4. Identify (A), (B), (C) and (D).
C
3
H
5
Cl (A)

dryether / Mg
(B)
+

H / O H ) ii (
CO ) i (
2
2
(C)

] O [
C
8
H
12
(D)
Saturated
Ans. (A) = ; (B) = ;
(C) = ; (D) =
5. Preparation of propanoic acid from ethyl alcohol follows :
Sol. CH
3
CH
2
OH

5
PCl
CH
3
CH
2
Cl

KCN
CH
3
CH
2
CN

+
H / O H
2 CH
3
CH
2
COOH
6. Identify (A), (B) and (C).
C
3
H
6
Cl
2
(A)
KCN
(B)

+
OH / O H
2
(C)
2
CO
A

2-Methylpropanoic acid
Sol.
Cl
|
CH C CH
|
Cl
3 3

KCN
CN
|
CH C CH
|
CN
3 3

+
OH / O H
2
COOH
|
CH C CH
|
COOH
3 3
2
CO
A

2-Methylpropanoic acid
7. Find the rate of soda-lime decarboxylation.
Rate of soda-lime decarboxylation. I > II > III > IV > V
8. Identify (A), (B) and (C).
CH
3
CH
2
COOH

P / ) eqV 1 ( Br
2 (A)

KCN
(B)

A
+
/ H / O H
2 (C)
(A)
Br
|
COOH CH CH
3
; (B)
CN
|
COOH CH CH
3
; (C) CH
3
CH
2
COOH
9. Write the structures of (A) C
3
H
7
NO which on acid hydrolysis gives acid (B) and amine (C). Acid (B) gives
(+)ve silvermirror test.
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CHEMISTRY
Ans. A = or
10. Predict A , B , C , D and E.
Acid (A)
A
B
3
AlCl / Mesitylene
Sol. (A) = CH
3
COOH; (B) =
O O
|| ||
CH C O C CH
3 3 ;
(C) = (D) =
11. Which of these represents correct reaction ?
l--- n = +i -=i ~lil+i =ti t `
(A*)

NaOD . conc
DCOO

+ DCH
2
OD
(B*) +

NaOH
C(CH
2
OH)
4
+ HCOO

(excess) (~ili+)
(C*)
+
2
Br P
(D*) +
O H
SO H . conc
2
4 2

Ans.

NaOD . conc
DCOO

+ DCH
2
OD (Cannizzaro reaction)
(B*) +

NaOH
C(CH
2
OH)
4
+ HCOO

(Aldol + Cannizzaro reaction)

(excess) (~ili+)
(C*)
+
2
Br P
(HVZreaction)
(D*) +
O H
SO H . conc
2
4 2

(Esterification reaction)
12. Which are correct against property metioned ?
l< n nii n +i-=i =ti t `
(A*) CH
3
COCl > (CH
3
CO)
2
O> CH
3
COOEt > CH
3
CONH
2
(Rate of hydrolysis) (n ~i- +i <)
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CHEMISTRY
(B*) CH
3
CH
2
COOH> > (Rate of esterification) ((-i+i +i <)
(C) > > (Rate of esterification) (((-i+i +i <)
(D) > > PhCH
2
COOH (Rate of decarboxylation)
(l+ii l+=ni+i +i <)
13. Match the product of column II with the reaction of column I.
Column I Column II
(A)

A
(p) ester with O
18
(B)

A
(q) A|-diketone with
18
OHgroup
(C)

A
(r) Acyclic anhydride with
18
OH group
(D)

A
O
/ OH
(s) A cyclic ester without O
18
Ans. (A) r ; (B) s ; (C) p ; (D) q.