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Chemistry Pre-Medical
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C 03 Reaction Mechanism - I
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01. Concepts to Understand reaction mechanism 43
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02. Type of bond cleavage 43
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03. Type of attacking reagent 43

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04. Reaction Intermediate 44

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05. Electronic effect 45

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06. Inductive effect 45

07. Resonance effect 49

08. Hyperconjugation effect 60

09. Electromeric effect 62

10. Tautomerism 62

NEET SYLLABUS

Electronic displacements in a covalent bond : inductive effect, electromeric effect, resonance and hyper conjugation. Homolytic
and heterolytic fission of a covalent bond : free radicals, carbocations, carbanions; electrophiles and nucleophiles.
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OBJECTIVES

After studying this unit, we will be able to :

• understand the concept of organic reaction mechanism;

• explain the influence of electronic displacements on structure and reactivity of
organic compounds;
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R-$++$30! ?<$#/%($(0! $++$30@A! E0! '2! %,2*! 3%,,$-! %2! 8*! .*(-! #$2*(%(3$! ?)'>$(! .C! 8%04$(! %(-! "%&$#@A
q $'(;&%&'(,)'>)+/">>"$%)-
<8 E+!04$#$!'2!KOR!s .*(-!%(-!<*2'0'>$!34%#)$!%#$!'(!3*(j;)%0'*(
K%#.*(! 14'34! '2! %00%34$-! 0*! <*2'0'>$,C! 34%#)$-! 3%#.*(! '2! 3%,,$-! %2! a! OK !%(- !R !14'34 !'2 !%00%34$- !0*
a OK!'2!3%,,$-!%2!a O!RA!D*!'+!(;/.$#!*+!a O!R!%#$!/*#$=!04$(!04$#$!1',,!.$!/*#$!(;/.$#!*+!4C<$#3*(j;)%0'()
20#;30;#$2=! 2*! /*#$! 20%.,$! 1',,!.$! 04$! 3%#.*3%0'*(A

Å
R R R R
a Å
R !K KRG ¬¾® R !K KRG ¬¾® R !K KRG ¬¾® R !K Å
KRG
Å
R R R R

%,,!%#$! 3%,,$-! %2! 4C<$#3*(j;)%0'()! 20#;30;#$2! *#! 3%(*('3%,!20#;30;#$2A

28 E+! 04$#$! '2! KOR! s .*(-!%(-!+#$$!$O! %#$!'(! 3*(j;)%0'*(! 04$(!04$#$!1',,!.$!R-$++$30A
K%#.*(=!14'34!'2!%00%34$-!0*!K!4%>'()! ;(<%'#$-! $O=! '2!3%,,$-!%2!aOK!%(-!R!14'34!%#$!%00%34$-!0*!a-K!%#$!3%,,$-
%2!a-RA
8
R R R R
a 8 8
R !K KRG ¬ ¾ ® R !K KRG ¬ ¾ ® R !K KRG ¬ ¾ ® R !K KRG
8
R R R R
21
78 E+!04$#$! '2!KOR! s! .*(-! %(-! p! .*(-!%#$! '(! 3*(j;)%0'*(! 04$(! 04$#$! 1',,!.$! R-$++$30A
0-

2<H!3%#.*(!14'34!'2!%00%34$-!0*!-*;.,$!.*(-$-!K!'2!3%,,$-!%2!aOK!%(-!R!%00%34$-!0*!aOK!'2!3%,,$-!%2!aORA
02

Å
R R R
:2

R
a 1 1 Å 1
R !K KR KRG ¬ ¾ ® R !K KR KRG ¬ ¾ ® R !K KR KRG ¬¾ ® R !K KR KRG
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R R Å R
R
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(530)-! E+!04$#$! '2!K—R! s! .*(-!%(-! ($)%0'>$!34%#)$! '(! 3*(j;)%0'*(! 04$(! 04$#$!1',,! .$!(*! R-$++$30A
Se

R
1
R !K KRG ?8*!R!-!$++$30@
R
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(*!24'+0'()!*+!K—R!s!.*(-=!.$3%;2$!%('*(!'2!4%>'()!3*/<,$0$!*30$0A!?8$O@
q #..@&$#%&'()'>)+/">>"$%
q ,31b4F43G)5f)21Eb5213456)/)>E00)!1d421F)/#Fk060

u D0%.','0C!µ!8*A!*+!3%(*('3%,!20#;30;#$2!µ!8*A!*+!a!RA

"x1mpF0)-)G'>$!20%.','0C!*#-$#!+*#!T-
KRH
?'@ KRH !K* > *
KRH !KR > *
KRH !KR > * ! C*)=) +/× D
!KR
G H

KRH KRH
9!a-R 6!a-R H!a-R Q$#*!a-R
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 ®
ALLEN Pre-Medical : Chemistry 61

* KRH * *
KR
?''@ !! > !! > G
C*)=)+/× D

7! a-R ! ! ! ! ! I !a-R ! ! ! ! ! ! ! ! F !a-R

M%x'/;/! 20%.,$
?'''@ KRH—KR KRG > KRG KRG

H!a-R Q$#*!a-R

! ! /*#$! 20%.,$

?'>@ D0%.','0C! *#-$#! *+! %,&$($2! 1',,! .$

KRH KRH KRH KRH KRH R KRH R

K! K! K! K! K! K! K! K!
KRH KRH KRH R KRH R R KRH

KRH KRH KRH R R R

K! K! K! K! K! K!
R R R R R R

21
q +013)5f)hGdE5g0613456)-
0-

B—KR KRG!U!RG!¾¾® B—KRG—KRH!U!DR!?R$%0!*+!4C-#*)$(%0'*(@

02

R$%0!$>*,>$-!14$(!%(C!;(2%0;#%0$-!4C-#*3%#.*(!'2!4C-#*)$(%0$-!'2!3%,,$-!4$%0!*+!4C-#*)$(%0'*(!?DR@
:2

?E+! %,&$($!'2! /*#$!#$%30'>$!0*1%#-2!4C-#*)$(! 04$(! '0!1',,!$>*,>$!/*#$! DR@

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<8 W4'34!*+!04$!+*,,*1'()!%,&$($!'2!/*20!20%.,$!?B!=!KRH@A

?F@!BGK KBG ?G@!B—KR KBG ?H@!B—KR KR—B ?I@!B—KR KRG

28 W4'34!*+!04$!+*,,*1'()!4%2!/'('/;/!4$%0!*+!4C-#*)$(%0'*(A
?F@!$04$($ ?G@!P#*<$($ ?H@!3'2-G-.;0$($ ?I@!0#%(2-G-.;0$($
78 W4'34!*+!04$!+*,,*1'()!'2!/*20!20%.,$A
?F@!K*(j;)%0$-!%,&%-'$($!?KRG KR—KR KRG@ ?G@!E2*,%0$-!%,&%-'$($!?KRG KR—KRG—KR KRG@
?H@!K;/;,%0$-!%,&%-'$($!?KRG K KRG@ ?I@! 7,,! %#$! $:;%,A
48 7/*()!04$!+*,,*1'()!04$!20#*()$20!%3'-!'2!T-
?F@!KRHK99R ?G@!K6R5K99R ?H@!/OKRH9K6RIK99R ?I@!<OKRH9K6RIK99R
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 ®
62 Pre-Medical : Chemistry ALLEN
!"#"#$ %&%'TROM%RI'$%FF%'T$:$(%$%ffect)

!"#$%&'&(')*+,-&)("-(*(,.*)&/($*0)("-((p1&%&c')"+,(-)"#("+&(*'"#('"(*+"'.&)(*'"#(0+($)&,&+c&("-(*''*ck0+g
)&*g&+',(0,(k+"w+(*,('E'(&--&c'.

(0) Positive$%elctromeric$%ffect$(+$%$effect)$:(I+('.0,(&--&c'('.&((p(1&%&c')"+,("-('.&(#u%'0$%&(b"+/(*)&
')*+,-&))&/('"('.*'(*'"#('"(w.0c.('.&()&*g&+'(g&',(*''*c.&/.(F")(&x*#$%&(:

Å
((((((((((((((((((((((((((((((((((((((((((((((((((((((((((((!(=(!(
((((((((((((((((((((((((((((((((((((((((((((((((((((((((((((!(–(!(
+ H+
(*''*ck0+g( H
)&*g&+')

(00) Negative$%lectromeric$%ffect$(-%$effect)$:(I+('.0,(&--&c'('.&((p1(&%&c')"+,("-('.&(#u%'0$%&(b"+/(*)&
')*+,-&))&/('"('.*'(*'"#,('"(w.0c.('.&(*''*ck0+g()&*g&+'(/"&,(+"'(g&'(*''*c.&/.(F")(&x*#$%&.

((((((((((((((((((((((((((((((((((((((((((((((((((((((((((((!(=(O(
((((((((((((((((((((((((((((((((((((((((((((((((((((((((((((!(–(O(
+ CN
(*''*ck0+g( !N
)&*g&+')

Shifting of p electrons :

Å 1
(i) !H2 )&*g&+'(
!H2 ¾¾¾® !H2 !H2
21
)&*g&+' Å 1
!H3 !H !H2 !H3 !H !H2
0-

(ii)
+I
02
:2

(*)
Å 1 1 Å
(iii) !H3 ! )&*g&+' or !H3 ! ! !H3
! !H 3 !H3 ! ! !H3
n

(*) (b)
io

(b)
ss
Se

)&*g&+'( 1 Å
(iv) !!%3 !H !H2 ¾¾¾® !!%3 !H !H2
–I

!"5 TAUTOM%RISM$OR$D%SMOTROPISM
Z:\NODE02\B0B0-BA\TARGET\CHEM\ENG\MODULE-3\03 GOC-I\01-THEORY.P65

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-)"#("+&($"%yv*%&+'(*'"#('"(*+"'.&)($"%yv*%&+'(*'"#.(T.0,($+&+"#&+*(0,(k+"w+(*,('*u'"#&)0,#.
l D&,#"')"$0,#(#&*+,(b"+/('u)+0+g.([D&,#",(=(B"+/(;(T)"$",(=(Tu)+]

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 ®
ALLEN Pre-Medical : Chemistry 63

"x8 ˆ†ˆ
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! ! &$0* $($!U! *,!=! $(*,

(530)- C<D)M%;0*/$#2!$x'20!'(!-C(%/'3!$:;','.#';/A
C2D!"C!24'+0'()!*+!RO%0*/=!p .*(-!%,2*!34%()$2!'02!<*2'0'*(A

C&D $56d43456)f5E)%1u35m0E4sm)-
C1D >5E)21Eb56GF)25mp5u6ds)-/)K%#.*(C,!3*/<*;(-2!4%>'()!%0!,$%20!*($!%30'>$-R ?aOR@!24*1!0%;0*/$#'2/

?'@ H!a R= 24*12!0%;0*/$#'2/A

?''@ 6! a R= 24*12!0%;0*/$#'2/

?'''@ F! a R= 24*12!0%;0*/$#'2/

?'>@ 8*!a R= 8*!0%;0*/$#'2/

?>@ 8*!a R= 8*!M%;0*/$#'2/

21
0-
02

?>'@ !?73$0*<4$(*($@ H! a R= 24*12!0%;0*/$#'2/!?73$0*<4$(*($@

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?>'''@ G!a R= 24*12!0%;0*/$#'2/

Z:\NODE02\B0B0-BA\TARGET\CHEM\ENG\MODULE-3\03 GOC-I\01-THEORY.P65

?'x@ I!a R= 24*12!0%;0*/$#'2/

?x@ a-R=!%00%34$-!2<G!3%#.*(!-*$2!(*0!'('0'%0$!'(!0%;0*/$#'2/

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 ®
64 Pre-Medical : Chemistry ALLEN
CbD >5E)643E5)25mp5u6ds)-)8'0#*!3*/<*;(-2!4%>'()!%0!,$%20!*($!%30'>$-R!?a O!R@!24*1!0%;0*/$#'2/

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8'0#*!+*#/ 73'('0#*!+*#/

?%3'-'3!+*#/!2*! 2*,;.,$!'(!.%2$@

C2D R—K 8!%(-!R—8! K!%#$!0%;0*/$#2![%,2*!F;(30'*(%,!'2*/$#2]!14',$!B—K 8!%(-!B—8 K!%#$

*(,C!F;(30'*(%,!'2*/$#2A

R—K 8 K 8—R

730'>$! R

9
CdD R 8 ! ! ! %(- R—9—8 9!%#$!0%;0*/$#2A
9

(530)-)8'0#*!3*/<*;(-2!1'04!%0!,$%20!*($!aOR!%#$!2*,;.,$!'(!8%9RA

C&&D "65F)$563063)-

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l M*#$!%30'>$!04$!R=! /*#$!1',,!.$!'02!<%#0'3'<%0'*(!'(! 0%;0*/$#'2/A

D0%.','0C!*+!$(*,!+*#/!-$<$(-2!*(! ?'@!B$2*(%(3$!%(-!?''@!R!O!"*(-!!?'''@!7#*/%0'3'0CA
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<8 W4'34!*+!04$!+*,,*1'()!-*$2!(*0!24*1!&$0*!$(*,!0%;0*/$#'2/A
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9 9

2A M%;0*/$#'2/!'2!-;$!0*!T-
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 ®
ALLEN Pre-Medical : Chemistry 65
78 W4'34!*+!04$!+*,,*1'()!4%2!4')4$20!$(*,!3*(0$(0A

?F@! ?G@!

?H@! 9KGR5 ?I@!

48 E(! 14'34! *+! 04$! +*,,*1'()!#$%30'*(! /*20! 20%.,$! $(*,!'2!<#$2$(0A

9 9 OH
R R
?F@! ! ! ?G@! ! !
R

9
9
?H@! ! ! ?I@! ! !
9

21
0-
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Qu08 F G
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#6s8 4 4 7
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 Chemistry Pre-Medical
©

C 03 Reaction Mechanism - I
h apter
ontents 11. Exercise-I (Conceptual Questions) 66
21
0-

12. Exercise-II (Previous Year Questions) 72

02
:2

13. Exercise-III (Analytical Questions) 77

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NEET SYLLABUS

Electronic displacements in a covalent bond : inductive effect, electromeric effect, resonance and hyper conjugation. Homolytic
and heterolytic fission of a covalent bond : free radicals, carbocations, carbanions; electrophiles and nucleophiles.
 ®
66 Pre-Medical : Chemistry ALLEN
EXERCISE-I (Conceptual Questions) Build Up Your Understanding

ATTACKING REAGENT I-EFFECT

1. !"#$"%&'%(")%'&**&+#,-%./)$#).%#.%0,%)*)$(1&/"#*) 1
7. CH 3 % % #.% *)..% .(0b*)%("0,% :-
234% 5NH2 224% SO3
Q
234%NO3 244%5OH 1 1
234%CH3— CH2 224%CH3— CH —CH3
GC0001
1 1
2. !"#$"%&'%(")%'&**&+#,-%0$(.%0.%0%,u$*)&/"#*)? 234% CH2 —NO2 244%CH3— CH —C2H5
Å
234% N O2 224% :CC*2 GC0005

8. D)$1)0.#,-%&1d)1%&'%–I%)'')$(%&'%(")%(1#0d%[–NO2,
Θ
234% N H2 244% · CH3 Å
– N H3 ,% –CN]% #.% :-
GC0002
Å
REACTION INTERMEDIATES 234% – N H3 % > %–NO2% > %–CN

3. !"#$"%&'%(")%'&**&+#,-%$&,(0#,.%&,*y%("1))%/0#1%&' Å
224% – N H3 % > %–CN %> %NO2
)*)$(1&,.%:
234%C01b0,#&, 224%C01b&$0(#&, Å
234% –CN% >% –NO2% > %– N H3
234%C01b&,%'1))%10d#$0* 244%N&,)
GC0003 Å
244% –NO2% > %–CN %> %– N H3
21
4. C01b0,#&,%#.%0%:-
GC0006
0-

234% B0.)
02

224%Nu$*)&/"#*) 9. M&.(%.(0b*)%$01b0,#&,%#.%:-
234%B&("%(")%0b&v)
:2

1 1
244%N&,) 234% HC C 224% H2C CH
n

GC0004
io

5. I,% +"#$"% .(1u$(u1)% $01b&,% d&).% ,&(% 0$(% 0.% 0 CH3

1 1
ss

)*)$(1&/"#*). 234% CH3–C CH2 244% CH3–C CH

Se

CH3 CH3
234%CH3–CH2–C*
224%CH3–CO–CH3 GC0007

10. T")%$&11)$(%&1d)1%&'%.(0b#*#(y%&'%-#v),%$01b0,#&,.%+#**
234% b)%:-
Z:\NODE02\B0B0-BA\TARGET\CHEM\ENG\MODULE-3\03 GOC-I\02-EXE.P65

244%CH3–CN
CH3–CH 2 CH 2=CH HC º C
GC0160
(I) (II) (III)
6. !1&,-%.(0()m),(%1)-01d#,-%m)("y*%$01b&,#um%#&,
Å 234%I%>%II%>%III 224%III%>%II%>%I
2C H3 4 .
234%I%>%III%>%II 244%II%>%I%>%III
234%I(%#.%./2%"yb1#d#.)d GC0008
224%V0$0,(%&1b#(0*%#.%./ "yb1#d#.)d
2%
11. !"#$"%#.%m&.(%b0.#$%0m&,-%(")%'&**&+#,-%:-
234% V0$0,(% &1b#(0*% #.% /)1/),d#$u*01% (&% m&*)$u*01
234%CH3NH2 224%CH3CH2NH2
/*0,01%0,d%#,%/u1)%/-&1b#(0*
234%NH3 244%2CH342CHNH2
244%I(%#.%)*)$(1&/"#*)%+#("%.)x()(%&'%)*)$(1&,
GC0009
GC0161

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 ®
ALLEN Pre-Medical : Chemistry 67
12. !"#$"%&'%(")%'&**&+#,-%"./%0.1#020%34.%5- 20. Arr.,-)% (")% '&**&+#,-% #,% (")% .$#d#$% /(r),-("
(1)%CH2FCOOH (2)%CH2C*COOH &rd)r%5
(3)%CH3COOH (4)%HCOOH (.)%NO2CH2COOH (b)%NC–CH2COOH
($)%CC*3COOH (d)%CHC*2COOH
GC0010
(1)%.%>%b%>%$%>%d (2)%$%>%d%>%.%>%b
13. !"#$"%&'%(")%'&**&+#,-%#/%0&/(%.$#d#$%? (3)%b%>%.%>%d%>%$ (4)%$%>%.%>%b%>%d
(1)%M)("&1y%.$)(#$%.$#d (2)%A$)(#$%.$#d GC0163
(3)%C"*&r&%.$)(#$%.$#d (4)%Tr#'*2&r&.$)(#$%.$#d R- OR M-EFFECT
GC0011
21. M&/(%/(.b*)%$.rb&$.(#&,%#/%5-
14. !"#$"%&'%(")%'&**&+#,-%/"&+%+%I-)'')$(%5-
(1)%–%OH (2)%–%OCH3 (3)%–%CH3 (4)%–%C* Å Å Å Å
GC0012 CH2 CH2 CH2 CH2

15. A0&,-%(")%'&**&+#,-%(")%0&/(%"#-"*y%#&,#/)d%#,%+.()r%#/5 (1)% (2)% (3)% (4)%

(1)%CH3CH2CHC*COOH
(2)%CH3CH2CC*2COOH C* NO2 OCH3
(3)%CH3CHC*CH2COOH
(4)%CH2C*CH2CH2COOH GC0017
GC0013
22. M&/(%.$#d#$%$&03&2,d%#/%5-
16. T")%/(r&,-)/(%.$#d%.0&,-/(%(")%'&**&+#,-%$&03&2,d/
#/%? (1)% OH
21
(1)%CH3CH2CH(C*)CO2H
(2)%C*CH2CH2CH2COOH
0-

(2)% CO2H
02

(3)%CH3COOH
(4)%HCOOH
:2

GC0014 (3)% H3C CO2H

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17. !"#$"%&'%(")%'&**&+#,-%.$#d/%#/%/(r&,-)r%(".,%.$)(#$
(4)%O2N CO2H
ss

.$#d%5-
Se

(1)%Pr&3.,&#$%.$#d (2)%F&r0#$%.$#d GC0018

(3)%B2(yr#$% .$#d (4)%I/&% b2(yr#$%.$#d
23. !"#$"%r)/&,.(#,-%/(r2$(2r)%&'%v#,y*%$"*&r#d)%#/%*)./(
GC0015
/(.b*)% 5-
18. !"#$"%&'%(")%'&**&+#,-%.$#d/%".v)%(")%*&+)/(%34. . ..
v.*2)% 5-
(1)%CH2 . ..
CH— C*
Z:\NODE02\B0B0-BA\TARGET\CHEM\ENG\MODULE-3\03 GOC-I\02-EXE.P65

C*
(2)% —CH
(1)% CH3 CH COOH
(2)% C* CH2 CH2 COOH (3)% — —C*
(3)% CC*3COOH
(4)% A**% ".v)% )q2.*% /(.b#*#(y
(4)%CHC*2COOH
GC0019
GC0016
19. I,%+"#$"%s%b&,d,%(")%#,d2$(#v)%)'')$(%#/%0#,#020%? 24. T")%/(.b#*#z.(#&,%d2)%(&%r)/&,.,$)%#/%0.1#020%#,
C—C—C—C—C*
(d) ($) (b) (.)
(1)% (2)% (3)% (4)%
(1)%. (2)%b (3)%$ (4)%d
GC0162
GC0020
E
 ®
68 Pre-Medical : Chemistry ALLEN
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 ®
ALLEN Pre-Medical : Chemistry 69
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70 Pre-Medical : Chemistry ALLEN
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ALLEN Pre-Medical : Chemistry 71

.HYPER$ONJU#ATION .TAUTOMERISM

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EXERCISE-I (Conceptual Questions) ANSWER KEY

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 ®
72 Pre-Medical : Chemistry ALLEN

EXERCISE-II (Previous Year Questions) AIPMT/NEET

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ALLEN Pre-Medical : Chemistry 73
AIPMT Mains-2011 AIPMT 2015

9. !"#$"%&'%(")%'&**&+#,-%$&./&0,12%#2%.&2(%342#$%? 13. I,%+"#$"%&'%(")%'&**&+#,-%$&./&0,12,%C–C*%3&,1

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 ®
74 Pre-Medical : Chemistry ALLEN
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