reaction is: 19 A pril.

2019 (Shift-1)1

6660
50. W h ich o r 1hc fo llowing co mpounds will form the
prccipilate with aq. AgNO 1 solution most readily?
14 S.p• 2020 (S bift-11)1
_,,,,....~ Br

,.,"°"'' '" ¢ OCH,

w hcrc.z -. C H1CH 1O -(A )or H 1 Ci--O-
IH,
CH,
(B)
A
(a) D < B < A < C
( c) D < A < C < B
B C
(b) A < B < C < D
(d) B < C < A < D

59. Increasing order of reactivity o f the following compounds

D

(c) o (Br k, and kc arc n-spcctivcly. thc ntlc CODSlllnts for substitution

and elimination reactions and µ =t. k

the correct op1ion

17Joo. 2021 (Sbift-11)1

for Si,, I subst itution is:

IA) } -c H,-CI
19 April, 2019 (S bi(1. IJ)I

(a) µA> µ 8 and kc (B) > kc (A)

,,/"-.._
51. In C 11rius meihod or estimation o f halogen. 0 .172 g o f an (8) H,C Cl
o rganic compound showed prcsmce o f0.08 g of bromine. (b) µ A > µ 8 and kc (A) > kc ( B)
Which of these is the conttt structure of the compound? ~ Cl
(C) µ 8 > µ A and kc (8) > kc (A)
12 Sq,1. 2120 (Sbift-1)1
(d) µ8 > µA and kc (A) > kc ( B) (C) H C O ~

,., ¢
1
NH.

'" "''9
54. The d ecreasing ord er or react iv ity of the following 56. Con s ider 1hc follo wing re ac tions. whic h o f t hes e ~ Cl
compounds towards nuclcophilic substitution (Ss2) is: rcaction(s) w ill noc produce Sayu:df product? ID ) v

1 1,c1 (a) (CH 1 ) 1CCH(O H)CH 1 ~ ( a ) ( B) < (C) < (D) < (A) (b) (A) < (Bi < (D) < (C)

(c) H1C- Br
Br
(d) H 1C-CH!- Br
Br
u( I)
(b) (CH,),C llCH(Br)ClJ,

(c) (CH 1):CHCH(Br)CH 1 ~

-=!e!!...+ (<) (8 ) < (Al < ( DI < (C) (d) (B ) < (C) < (A) < (D)

60. The: major product o bta ined in !he gi\'cn reaction is

Cll"O'O'- ,.....011....._c;-11 ,.....c111
52. The m ajor produc1 ob lai ncd from E, - c limin alio n o f (d) (Cl9 11-CH lCHO ~ 1
I Clll AICI
3-bromo -2-0 uoropcnlanc is 12 ~pL
2020 (S lllft-11)1
Oi l
~ Ci ~ Produc1
Br o, Which of thck rcac tio n( s) will not produce Saytteff

(a) rn, CH,-CII-CH - CH,

I I product'! 17 Jaa. 2120 (Shin-1)1
I 10 April, 2019 (Sbln-11)1
o. cu~o....._ ,.,,,,cu, ,.,,,,cu,
F
( II) . (a ) (bl and (d)
I<) (a ).(<) and (d)
(bl (c) only
(d) (d) only
( a) V CH, CH
I I
(b) CH,-CU • CII-CII- CH, 57. The decreasi ng o rder of rcac1ivi1y lowards dchydro-
CH,Cll,Cll • -F halogcnation (E1) reaction o f 1hc fol low ing compounds is:
(c )
1C H,
I
NO, 11 Joa. 2129 (Sbln-111

(d) CH, - C11,-C •

Br
I
CII-CH,
NO,
( Ill )
(A) CI~ (BI CJ~

I<)
cu,'OC2
I
o ,.,_
II CJ
(C) ' ( " ' - ID) ~
53. In lhc following rc11elion seq uence , slruclurc o f A lllld B
Cl Cl H,
rcspcclivd y will he I
NO (a) D > B > C > A ( b) B > A > D > C
0, ' C~H,
J'. .j ~ ~ (lntcnnolccular p roducl)B
. ( IV)

iJ S.p<. 2020 (Sbln-11)1

(c) B > D > C > A (d) 8 > D > A > C
51. T he incre asin g o rde r o f rcac t i\·ity of the followi ng
compounds lowards aromatic d ecuophilic substilution
(d) CH,
""1
,.,_
LQlCH,Br (a) ( II) > (Ill) > (I) > (JV )(b) ( Ill) > ( II) > (IV) > (I)

17 J■■, 2020 (S blft-11)1 le) (ll) > l lll) > (IV) > (l)(d) (J V) > (ll) > (lll) > (l )
25
24

61. Which one of1hc following is like ly to gi\·e • pm:-ipitate

wilh AgNOJ solulion'! (12 April 2019 (S hift-11)1
6'. The major prodoct of 1hc following reac1ion is
CH .CIIJ
66. Which of the follow ing polcnlial energy (PE) diagrams
~ presents 1hc S :. 1 reaction'! 19 ApriL 20 19 (Slllft- 11 )1
(a)g o(bion
IT
(a) C H: • CH - CI ' • N.oEt
t
(c)on go
(b) CIJCJ, 11c- cI- c1 -
1
,, Br Br
(c ) (C H 1) 1CCI (a) PE
(d) CCI, COOCl-l?Cl-11
(d)
Progress of reaction -
62. The major producl of the following rcacl ion is
CH,

A
y . ,c,,-. ai ttp.~
1a1
CH 1CH: C• CH:
I
CO:CH: CH 1 ,.,J~
HO HO
'9. Heat ing of 2-chk>ro- 1-phcnylbutanc with EtOK/EtOl-1
g ives X as the major p rod uct. Reacl ion of X wi th
Hg(OAc)/ Hp followed by NaBH~ gi\'c:s Y as 1hc major

, ,iI T
Cl Progress of reaction - product. Y is (12 Ap ril, 20 19 (Shlft-11)1
CO:CH:CH1
11 April2019 (S hift-II ii (b) I (a)l'h~

(a)¢ CH .O H CHCI. CH1C-CHCH1 0 11

(bl¢ .
r ,cu, (bi
?"
,.,--....,A
Ph
(cl 111c - c - oc:11?cH1 Progress of rcacttOn -
Cl
Cl
I (c) ~
?"

1,¢
CO ,H C HO CCXX:l-1:Cl·IJ Ph

(d) PE
t
, H,CH,
(,/) ¢
(d) HlCll :c - c- cO:Cll:Cllj Progress ofrcaclion-
Cl Cl
I
CH
67. The major product of the following reaction is
6J. The major producl ·r in the following rcac1ion is: 1
CH

Cl, 1 E10Na X ~y c1-1J-{-i1-1 c1-1) ~

I "' --ire..-
65. An · Assertion' and • · Reason· • ~ given below. Choose
I.he corrccl answer from the following options:
II Br 111April2119(Sblft-1)1
CH,
' " Apri• 2019 (S bift-11)1 Aswrdoa (A): Vinyl halides do not undergo nuclcophilic (b) CH1-{--e1-1-=CII:
substitution easily. ll
la ) }___ <;H, <;H,
B) - RnlOII (R): Even though 1hc in1enncdia1c ca rbocation
is s1abilizcd by k>oscly held it-electrons. the clea,•agc is
(c) CI-IJ-C.'-CH C H) 1dl cH,~i" en,
H OCH 1
difficull because or s1rong bonding.
68. The major product o f 1hc foUo wing reaction is :
(b) HO~ 112 Apri. 21 19 (Sbln-11)1
(a) Both (A) and (R) arc wrong stalcmcnts.
£'le, ( I) KO ll(,qurous)

(c ) r .._
Br-J_ (b) Both (A)and (R) arc com:c1statements and (R) is the
conttl explana1ion of (A).
B
~ ~ (2) CrOJn 1·
(3) H,SO/ A
(c) Both (A) and (R)arecorrcc1 s1a1~nts bu1 (R) isnot 110 Ap,ll. 2019 (ShlR-1)1
19 Jaa. 2119 (Sllift-1)1
the corrccl explanation of (A). (a) (A ) < (B) < (C) < JD) lb) ( B) < (A) < (C) < (D)
(d)Br+
(d) (A) is acorrcc1staecmmt bu1 (R) is a \loTOOg statcmcnl. le) (B) < (A) < (D ) < (C) (d) (A) < (B) < (D) < (C)

27
26
 reaction is: 19 A pril. 2019 (Shift-1)1

6660
50. W h ich o r 1hc fo llowing co mpounds will form the
prccipilate with aq. AgNO 1 solution most readily?
14 S.p• 2020 (S bift-11)1
_,,,,....~ Br

,.,"°"'' '" ¢ OCH,

w hcrc.z -. C H1CH 1O -(A )or H 1 Ci--O-
IH,
CH,
(B)
A
(a) D < B < A < C
( c) D < A < C < B
B C
(b) A < B < C < D
(d) B < C < A < D

59. Increasing order of reactivity o f the following compounds

D

(c) o (Br k, and kc arc n-spcctivcly. thc ntlc CODSlllnts for substitution

and elimination reactions and µ =t. k

the correct op1ion

17Joo. 2021 (Sbift-11)1

for Si,, I subst itution is:

IA) } -c H,-CI
19 April, 2019 (S bi(1. IJ)I

(a) µA> µ 8 and kc (B) > kc (A)

,,/"-.._
51. In C 11rius meihod or estimation o f halogen. 0 .172 g o f an (8) H,C Cl
o rganic compound showed prcsmce o f0.08 g of bromine. (b) µ A > µ 8 and kc (A) > kc ( B)
Which of these is the conttt structure of the compound? ~ Cl
(C) µ 8 > µ A and kc (8) > kc (A)
12 Sq,1. 2120 (Sbift-1)1
(d) µ8 > µA and kc (A) > kc ( B) (C) H C O ~

,., ¢
1
NH.

'" "''9
54. The d ecreasing ord er or react iv ity of the following 56. Con s ider 1hc follo wing re ac tions. whic h o f t hes e ~ Cl
compounds towards nuclcophilic substitution (Ss2) is: rcaction(s) w ill noc produce Sayu:df product? ID ) v

1 1,c1 (a) (CH 1 ) 1CCH(O H)CH 1 ~ ( a ) ( B) < (C) < (D) < (A) (b) (A) < (Bi < (D) < (C)

(c) H1C- Br
Br
(d) H 1C-CH!- Br
Br
u( I)
(b) (CH,),C llCH(Br)ClJ,

(c) (CH 1):CHCH(Br)CH 1 ~

-=!e!!...+ (<) (8 ) < (Al < ( DI < (C) (d) (B ) < (C) < (A) < (D)

60. The: major product o bta ined in !he gi\'cn reaction is

Cll"O'O'- ,.....011....._c;-11 ,.....c111
52. The m ajor produc1 ob lai ncd from E, - c limin alio n o f (d) (Cl9 11-CH lCHO ~ 1
I Clll AICI
3-bromo -2-0 uoropcnlanc is 12 ~pL
2020 (S lllft-11)1
Oi l
~ Ci ~ Produc1
Br o, Which of thck rcac tio n( s) will not produce Saytteff

(a) rn, CH,-CII-CH - CH,

I I product'! 17 Jaa. 2120 (Shin-1)1
I 10 April, 2019 (Sbln-11)1
o. cu~o....._ ,.,,,,cu, ,.,,,,cu,
F
( II) . (a ) (bl and (d)
I<) (a ).(<) and (d)
(bl (c) only
(d) (d) only
( a) V CH, CH
I I
(b) CH,-CU • CII-CII- CH, 57. The decreasi ng o rder of rcac1ivi1y lowards dchydro-
CH,Cll,Cll • -F halogcnation (E1) reaction o f 1hc fol low ing compounds is:
(c )
1C H,
I
NO, 11 Joa. 2129 (Sbln-111

(d) CH, - C11,-C •

Br
I
CII-CH,
NO,
( Ill )
(A) CI~ (BI CJ~

I<)
cu,'OC2
I
o ,.,_
II CJ
(C) ' ( " ' - ID) ~
53. In lhc following rc11elion seq uence , slruclurc o f A lllld B
Cl Cl H,
rcspcclivd y will he I
NO (a) D > B > C > A ( b) B > A > D > C
0, ' C~H,
J'. .j ~ ~ (lntcnnolccular p roducl)B
. ( IV)

iJ S.p<. 2020 (Sbln-11)1

(c) B > D > C > A (d) 8 > D > A > C
51. T he incre asin g o rde r o f rcac t i\·ity of the followi ng
compounds lowards aromatic d ecuophilic substilution
(d) CH,
""1
,.,_
LQlCH,Br (a) ( II) > (Ill) > (I) > (JV )(b) ( Ill) > ( II) > (IV) > (I)

17 J■■, 2020 (S blft-11)1 le) (ll) > l lll) > (IV) > (l)(d) (J V) > (ll) > (lll) > (l )
25
24

61. Which one of1hc following is like ly to gi\·e • pm:-ipitate

wilh AgNOJ solulion'! (12 April 2019 (S hift-11)1
6'. The major prodoct of 1hc following reac1ion is
CH .CIIJ
66. Which of the follow ing polcnlial energy (PE) diagrams
~ presents 1hc S :. 1 reaction'! 19 ApriL 20 19 (Slllft- 11 )1
(a)g o(bion
IT
(a) C H: • CH - CI ' • N.oEt
t
(c)on go
(b) CIJCJ, 11c- cI- c1 -
1
,, Br Br
(c ) (C H 1) 1CCI (a) PE
(d) CCI, COOCl-l?Cl-11
(d)
Progress of reaction -
62. The major producl of the following rcacl ion is
CH,

A
y . ,c,,-. ai ttp.~
1a1
CH 1CH: C• CH:
I
CO:CH: CH 1 ,.,J~
HO HO
'9. Heat ing of 2-chk>ro- 1-phcnylbutanc with EtOK/EtOl-1
g ives X as the major p rod uct. Reacl ion of X wi th
Hg(OAc)/ Hp followed by NaBH~ gi\'c:s Y as 1hc major

, ,iI T
Cl Progress of reaction - product. Y is (12 Ap ril, 20 19 (Shlft-11)1
CO:CH:CH1
11 April2019 (S hift-II ii (b) I (a)l'h~

(a)¢ CH .O H CHCI. CH1C-CHCH1 0 11

(bl¢ .
r ,cu, (bi
?"
,.,--....,A
Ph
(cl 111c - c - oc:11?cH1 Progress of rcacttOn -
Cl
Cl
I (c) ~
?"

1,¢
CO ,H C HO CCXX:l-1:Cl·IJ Ph

(d) PE
t
, H,CH,
(,/) ¢
(d) HlCll :c - c- cO:Cll:Cllj Progress ofrcaclion-
Cl Cl
I
CH
67. The major product of the following reaction is
6J. The major producl ·r in the following rcac1ion is: 1
CH

Cl, 1 E10Na X ~y c1-1J-{-i1-1 c1-1) ~

I "' --ire..-
65. An · Assertion' and • · Reason· • ~ given below. Choose
I.he corrccl answer from the following options:
II Br 111April2119(Sblft-1)1
CH,
' " Apri• 2019 (S bift-11)1 Aswrdoa (A): Vinyl halides do not undergo nuclcophilic (b) CH1-{--e1-1-=CII:
substitution easily. ll
la ) }___ <;H, <;H,
B) - RnlOII (R): Even though 1hc in1enncdia1c ca rbocation
is s1abilizcd by k>oscly held it-electrons. the clea,•agc is
(c) CI-IJ-C.'-CH C H) 1dl cH,~i" en,
H OCH 1
difficull because or s1rong bonding.
68. The major product o f 1hc foUo wing reaction is :
(b) HO~ 112 Apri. 21 19 (Sbln-11)1
(a) Both (A) and (R) arc wrong stalcmcnts.
£'le, ( I) KO ll(,qurous)

(c ) r .._
Br-J_ (b) Both (A)and (R) arc com:c1statements and (R) is the
conttl explana1ion of (A).
B
~ ~ (2) CrOJn 1·
(3) H,SO/ A
(c) Both (A) and (R)arecorrcc1 s1a1~nts bu1 (R) isnot 110 Ap,ll. 2019 (ShlR-1)1
19 Jaa. 2119 (Sllift-1)1
the corrccl explanation of (A). (a) (A ) < (B) < (C) < JD) lb) ( B) < (A) < (C) < (D)
(d)Br+
(d) (A) is acorrcc1staecmmt bu1 (R) is a \loTOOg statcmcnl. le) (B) < (A) < (D ) < (C) (d) (A) < (B) < (D) < (C)

27
26
 u1'
8 OCH,

J
~H, J5. Ma1ch Lisi-I with Lisi-II: J7. The conut ordcrof reacliviiy of the given chlorides with
(a) H1C-CHBr-C,H 5 and List-I List-II aceta1c in acctic acid is: Ill Aug, 2021 (SbiR-1)1
(<) 0
a
6- s
,
(A) (I) Wunz

1':C J:CH, tNH, u",a reaction

y
_!!fr.. Cl& C,H Cl CIO C H,

(b) (J H, and OCH, (B)

©["'a· ,.~
a
6-s,
(II) Sandrncycr
reaction
(a)

Y CH 1
,/,,
>

>
,/,,

CH,CI

Cf
,/,,

y
B,~IC H, (d)
(C) (Ill) Finig
H 2CHJCH~C I + 2Na ~
reaction

&
(<) H,C-CHBr-C, H, and NH, C!H,-C!H, + 2NaCI
CH, Cl Cl U C H,CI
(D) (I V) Gallennan
2c. H, CI + 2Na ~ (b) > >
c . H,-C.JIJ + 2NaCI rcaclion
Br ,/,, ,/,,
J2. In the gi\'cn reaction.

• 9rn~,,,~~'-""• lA Iii l Ma,. TIIF

◄ ii) Methyl
(ui l ll,0/H'
bnuoa~

°6-0
OH
Choose 1he COITCC:t answer from the op1ion given below:
(o) (A) - ( II~(Bl - ( I ). (C) - (IV). (D ) - ( Ill)
(h) (A)· (Ill). (Bl· (I V). (C) • (I). ( D) · (II)
(<) (A) - ( II). (8) - ( I V). (C) - ( 1). (D ) - ( Ill)
CHI

(d) (A)· (Ill). (B) · (I). (C) · (I V). ( D) · (II)

"A'canbc 125 Joa<. 2022 (SblR-1111
36. Whal is A in the following rc:action'!
I. q:111, :::;:',!' A
(a) Bcnzyl bromide 0

8,
tnhC)"klllc-...-.-
(1\1 11,,N,

The major product o f1hc above reaction is

M ajor Pmdui.1 (bl Bromob<nzrn<
(c) Cydohc:xyl bromide
(d) Methyl brom ide

Cl
~ C l l:Bt
o¢
~

--~e~o_ _•
e0
SK

124 J■-<. 2022 (SblR-1)1 V

,~T~~ l!!Q!4
11110tt 11 0 IMtjor l"Nducl)
1
OCH,
JJ. p
127 Joly. 2121 (Shlft-11 )1

·• Urn"'.&"·Cf"
ll:O f M-,orProdut·O

Consider the above rc-.aclion. the number of :t electrons ~ CH: NII:

(ti) present in the product · p· is _ _ . (o) ~)J
NII, 124 Jun<. 2022 (SblR-11 )1
.34. Given below arc t\.lo'O statements: Cl-11
Sla ftmr■t I: C:HP H and AgCN both can generate
(b) c l ' NII--Cll, - 0
nuclcophilc. > C I O CII,
SlattmHt II : KCN andAgCN both will gcncralc nilrile 0
nuc lcophilc with a ll reaction conditions.

' 'CC("
Choose the mosl appropriate option: JI. The product fonncd in 1hc: lirsl step of lhc reaction o f
111 Marth, 2021 (ShlR-11 )1 B,
(a) Both statement I and stalemmt U arc false. I
CH - C H! - CH - CH! - ~ 111 - CH1 1,1,•ith excess Mg/Et!O
(b) Slalrmcnl I is false but stalcmrnt II is true.
(E1 • C:H,) is: Br
(C') Both statcmcnl I and stalemmt U arc true. ( d ) a Cll,011
124 •·m. 2021 (ShlR-1)1
(d) Sta1cmcn1 I is 1ruc but stateme nt II is false.

21
20

44. The major product (A) formed in the n::aclion given below 46. The major producl in the following reaction is:
(a) 11,C - CH - TII - Cll, - r - c 11,
is 127 Aoi,. 202 1 (Sbift-11)1 I
H,C - CH - CHi - C H - C H: - CH ,
Cll,--CII©
. 11--Cll,-B, , ,~
. T~. , ~
lln1
_,,,0 1.
(b) CH, - CH'-i-H~ CH, + cu,8 at,OII A ll S.pl. 2020 (Shln-11)1
0 (Major Producl)
lo) ~ (b)K
(<) CH, _ CH, - TH _ CH, - T II _ CH,

CII, - CH, - CH - Cll, - CII - CH,

rgBr
(a) (iv) < (i) < (iii) < (ii)
(b) (i,•) < (iii) < (ii) < (i)
(c ) (i) < (ii) < (iii) < (iv )
(<),y 01-Bu

<~>-("
(d) CH,CH, - CH - CH, - T H - CH, (d) (i,·) < (i) < (ii) < (iii) 47. The decreasing order o f rcac1 ivi1y of!he fol lowing organic

'" '"·~@"·- "·

42. The cOll'ttl decreasing order of densities of 1hc following molecules to wards AgN01 solu1ion is
MgBr
compounds is: 14 S.pl. 2020 (SblR-111
J9. Presence of which reagent w ill affect 1hc rc,•crsibili1y

(A)L.
Cl
o f the following n::aclion. and change it to a irrcvcniblc
reaction:

C H , + I: ....::... C HJ I + HI 127 J• I)'. 2121 (Sllln-1)1

<•>O (b) v
f " ' Y CI a
(8 ) l__ O Mc
(o) IIOCI Cll,--Cll~.--C
oll--Cll,Br (C) CH,THCH, (D ) CH,THCH, NO,
(b) Liquid NH , Cl Cl

I~~
(c) dilute 1-INO: (<) (o) (8) > ( A) > (C) > (D) (b) (A) > (B) > (D) > (C)
(t/) C onccntraled Hl0 1 (<) (A) > (B) > (C) > (D) I~ (C) > (D) > (A) > (B )
(<) ~
40, What is the major product formed by HI on reaction with 41. The mechanism of S"' I reaction is gi,•cn as:
H,

,. '"·~@"'
11,c °"c _,,, n t.,.CH ., ~ Cl ~ Cl 0 0 0 0 0
R- X - R X - r f 11 X !. R- Y + X
125 Joly. 202 1 (Sbift-11)1 lon pa1r Sol\·tnl
H,C/ ~H, . ~ltdlDft
124 •·m . 2121 (Shin-I)I
"'"
r·
l o) (C) > (8) > (A) > (D) (b) (A) > (8) > (C) > (D)
(<) (D) > (C) > (8) > (AI (d) (C) > (Dl > (A) > (8) A student writes ~-aicral characteristics based on the given
mechanism as: fl Stpt. 2020 (Shlft, 1)1
(o) Cll, - T - TII - CH, 4.3. The major product of the fo llowing rcac1ion is
45. Consider 1hc reaction sequence gi\•en below : (A) The react ion is fa,·ourcd by weak nuckophilcs.

&
CH , I
(B) R would be easily formc:d if the subst ilucnts arc
CH,
7 or~ 11 0 - OH + er8 bulky.
I N.011 . : ra1c • k(1-Bu8r) ·· .(I)
I C 11110 11 MaJor Product (C) The reaction is accompanied by raccm i:r.ation.
Cll, - T - TII - CH,
(b )
I J'.:: + HOH + Br"
(0) The reaction is favoure d by non-polar solvents.

~ ll:C ~:~ • k(t-BuBr)IOHi8

I C H1 Ill Aus, 202 1 (Sbift-11)1 Which observalio ns arc corrccl'!
...(2)
(o) (B) and (D) (b) (A). (8 ) and (C)
(<) Cll, - T" - TII - Cll, - CH,
Which oflhe following slalcmcnts is lruc? (<) (A) and (C) (~ (A) and (B )
CH, I

O<
H, (a) Ch anging 1hc conccnlralion of base will have no 49. Among 1hc following compounds. which one has the
,11, (bl
H
effect on rcaclion (2) shoncs1 C - Cl bond? 14 S.p1. 2020 (Sbin-11)1
(b) Ch anging the concentration of base will have no H1C .,......c l
(d) Cll, - T - I H - CH,I effect on reaction ( I ) (o) H,C4-CI (b) lH
CH, H (c) Changing lhc base from OH
e1Tec1 on reac1ion (2)
to OR will have no t H, C H:

4 1. The correct order of the following eom poun& showing ,...-"y'CH,

increasing tendency towards nuclrophilic subs1itu1io n (d) L_J (ti) Doubli ng the concentration of base will double the (<) H,C - Cl (~ H0 I
reaction is: 124 t,· d,. 202 1 (Sllift-11)1
ralc of both the reactions 12 Stpc. 2121(Sllifll-U)I CH,

23
22
 OCH,

(a) H1C-CHBr--C,H 5 and uJ :' B~H,

(<) 0
J5. Ma1ch Lisi-I with Lisi-II:
List-I
a
List-II
J7. The conut ordcrof rcacliviiy oflhc given chlorides with
aceta1c in acetic acid is: Ill Aug, 2021 (Sbin-1)1

"' ((··~9'"'
(A) (I) Wunz

-NH, a•,a ..!!fr.. O•s, reaction

Cl& C,H Cl CI O C H,

OCH, (B)

©["'a· ,.~
a
6-s,
(II) Sandrncytt
reaction
(a)

Y CH 1
,✓,;
>

>
,✓,;

CH,CI

Cf
_✓,;

y
B,~ICH, (d)
(C) (Ill) Finig
H 2CHJCH~CI + 2Na ~
reaction

&
(<) H,C-CHB,-C,H, and NH, C!H,-CtH, + 2NaCI
CH, Cl Cl U C H,CI
(D) (I V) Gallerman
2c. H,CI + 2Na ~ (b) > >
B, c . H,-e. H, + 2NaCI rcaclion
,✓,; ,✓,;
J2. In the gi,•m reaction.
J26 •·<h. 2121 (Sh;ft.11)1

°6-0
OH
Choose 1he cOITCC:t answer from the option given below: Cl-l1
lA Iii l Ma,. TIIF (o) (A). (II~ (B) . ( I ). (C). (I V). (D ). ( Ill)
◄ ii) Methyl bnuoa~ (h) (A)· ( Ill), (B ) - (I V), (C) - (I), ( D) • (II)
(ui l ll,0/tf
(<) (A). ( II~ (B) . ( I V). (C) - (I). (D ). ( Ill)

,.Ya,
6''
(d) (A)· ( Ill), (B ) - (I), (C) • (I V), ( D) • (II)
"A' canbc 125 Joa•. 2022 (SblR-11 11
36. Whal is A in the following react ion'!
hlN.CN (o) Bcnzyl bromide 0
uuot r A
11,iK')"klllc-,._
(1\1 11, , N,

The major product o f1hc above reaction is

M ajor Pmduc1 (b) Bromob<nun<
(c) Cyclohcxyl bromide
(d) Methyl bromide

Cl
~ C l l:Bt
o¢
'S..

--~e~o__•
e0
SK

124 Ju•. 2022 (SblR-1)1 V

,~T~~ l!!Q!4
11110tt up t M11or l"NJucO

.. arn,d,&",y d
OCH,
JJ. p
ll:O f M-,orProdut·O
127 Joly. 2121 (Shlft-11 )1
Consider the above rc-.aclion. the number of :t electrons ~ CH: NII :
(ti) present in the product · p· is _ _ . (o) ~)l
NII, 124 J ua•. 2022 (SblR-11 )1
.34. Givm below arc two statements: C l-l1
Sla ftmt■t I: C:Hp l-1 and AgCN both can genera te lb) ~ Nlt-Cll, - 0
nuclcophilc. > C I O CH ,
OCII, SlattmHt II : KCN andAgC N both will gcncralc nilrilc
0

J
nuclcophilc with all reaction conditions.

'"°i"
Choose lhc mosl appropriate option: JI. The product fonncd in 1hc: ftrs1 step of lhe reaction o f
(b) Ill Marth. 2021 (ShlR-11)1 B,
(a) Both statcmrnl I and stalemmt U arc false. I
I NH, C H - CH! - C H - CH! - C ll1 - CH 1 1,1,•ith excess Mg/Et 1O
(b) Slalrmcnl I is false but Slalrmrnt II is true.
(Et • C:H,) is: ~r
(C') Both statcmcnl I and stalemmt U arc true. ( d ) a C ll,OII
124 •·<h. 2021 (ShlR-1)1
(d) Sta1rmcn1 I is 1ruc but statement II is false.

21
20

44. The major product (A) formed in the react ion given below 46. The major producl in the following reaction is:
la) ll,C - CH - TII - Cll, - r - c 11,
is 127 Aoi,. 202 1 (Sbift-11 )1 I
~
H,C - CH - Cl-Ii - C H - C H: - CH ,
Cll,-CI.I ©
11-Cll,-B, . T)._.. .
, ,)._. IIHI

_,,,e11.
(b) CH, - CH'-i:H~ CH, + C H,8 at,OII A ll S.pt. 2020 (ShlR-11)1
0 (Major Producl)
K
c•,-•@••~"
I• ) ~ (b)
(<) CH, - CH, - TH - CH, - T II - CH,
(a) (iv) < (i) < (iii) < (ii) Ot-Bu
CII, - CH, - CH - Cll, - CII - CH, <•>
(b) (iv) < (iii) < (ii) < (i)
(d)>-<:
rgB, (c ) (i) < (ii) < (iii) < (iv )
(<) ~

(d) C H1C H? - C H - CH: - ~ H - C H1 (d) (i\·) < (i) < (ii) < (iii) 47. The decreasing order of reac1 ivi1y of the fol lowing organic

Mg Br
39. Presence of which reagent w ill affect the rc,•crsibili1y
o f the following reaclion. and change it to a irTe,,enible
reactio n:
42. The corm:1 decreasing ordci- of densities of 1hc following

(a)o
compounds is:

f " ' Y CI
,., rn,-@••- "• molecules towards AgNO1 solu1ion is

(A)L. a
(8 )
14 S.pt 2020 (Sblh-1)1
Cl

l__
(b ) v
CH, + I: ....::.. CH1I + HI 127 J■I)'. 2821 (Sllln-1)1 OMc
(a ) IIOCI Cll,-Cll~,-C
o l l-Cll,B, (C) CH,THCH, (D ) CH,THCH,NO,
(b) Liquid NH , Cl Cl
(c) dilute HNO: (<) (o) (8) > (A) > (C) > (D) (b) (A) > (B ) > (D) > (C)
(ti) Concentraled Hl0 1 (<) (A) > (B) > (C) > (D) (d) (C) > (D) > (A) > (B )
(< ) ~ Id) ~
40, What is the majo r product formed by HI on reaction with 41. The m«hanism ofSs l reaction is gi,•cn as:
H,

,. rn,-@"•
11,c °"c _,,, n t._CH , ., ~ Cl ~ Cl 0 0 0 0 0
R- X - R X - r f 11 X !. R- Y + X
lonpa1r Sol\'C'nt
,.. ,
11,C / ~H, . 125 Joly. 202 1 (Sbift-11)1
12• •·<h, 2121 (Shin-I)I SC'paolttd IDft
lo) (C) > (B) > (A ) > (D) (b) (A) > (B) > (C) > (D)

t·
(o) Cll, - T - TII - CH,
(<) (D) > IC) > (B) > (A) (d) (C) > (D) > ( A) > (B)

4.3. The major prod1JCt of the following rcac1ion is

A student 'to'Titcs ~-a1cral characteristics based on the given
mechanism as: ll Stpt. 2020 (Shlft. J)I
45. Considcr !he reaction sequence gi\•en below: ( A) The react ion is f8\'ourc d by weak nuc lcophilcs.

&
CH1 I
(B) R would be easily formed if the substilucnts arc
CH
7 or~ - OH + er8 bulky.
I• I N.011 • ll:O ra1c • k(1-BuBr) .. ,( I)
C:H,OII Ml Jot Product (C) The react ion is accompanied by raccm i7.ation.
(b ) Cl-1, - T - TII - CH,
I J'.:: + IIOH + B," (0) The react ion is f8\'ourcd by non-polar solvcnt!l.

~ ~:~
I CH1 Ill Aua. 202 1 (Sbift-11)1 Which observatio ns arc cotTccl'!
ll:C • k(t-BuBr)IOHf' ...( 2 )
(o) (B) and (D) (b) (A). (B ) and (C)
I<) Cll, - r - ? - Cll, - CH,
Which oflhe following slalcmcnts is lruc? (<) (A) and (C) (d) IA) and (B)
CH 1 I

O<
H, (a) Ch anging 1he conccnlralion of base will have no 49. Among the following compounds. which one has the

r
(d) Cll, - T - ) 11 - CH,I
(b)
H
effect on n::aclion (2)
(b) Ch anging the concentration o f base will have no
effect on reaction ( I )
shorlcs1 C - Cl bond?

(o)
H1C
H,C4-cl
14 S.pt. 2020 (Sbin-11)1

(b)
,......ct
}H
CHJ H (c) Changing !he base from OH
effect on rcac1ion (2 )
10 OR will have no t H, CH:
4 1. The corn::c1 order of the following com poun& showing , / ' y CH,
increasing tendency 1owards nuclcophilic substitutio n (d) L_J (d) Doubling the concentra1ion of base will double the (<) H,C - CI (d) H0 I
ralc of both the reactions 12 Stpc. 2121(Slllifll-ll)I CH,
reaction is: 124 Fd». 202 1 (Sllift-ll)I

23
22
 (YH,
C H,Br

(<)
OCH,

0
J5. Male h List-I with List-II:
List-I Lnt-11
J7. The correct order of rcacti\'ity of the given chlorides with
acetate in acetic acid is: Ill Aug, 2021 (Shirt-1)1
(A) Cl ( I) Wunz

,Br 9 C H, tNH, a-•,a .!!fr.. (}s, n:aclion

Cl&CH
, Cl CI OCH,

(b) (
: ( I
H,
and OCH, (B)

©fs,a cu.-.
Cl

(}s,
( II) Sandmcycr
rcaclio n
(a)

Y CH1
o
>

>
o
CH,CI

y Yc,
Br~ICH, (d) a 0
(C) (Ill) Fiuig
H 2CH1 CH!CI + 2Na ~
rcaclion

&
(<) H,C-CHBr-C,H, and NH, C!H,-C1H, + 2NaCI
CH, Cl a CH,CI
(D) (IV) Ganerman
2C. H,Cl + 2Na ~ (b) > >
reaction
Br
J2. In the given re-action.
c .H,-C. H, + 2NaCI o o
126 F<b. 2021 (Sbift-11)1

y 06-0
ACH, OH
Choose the: correcl answer from the: oplion gi\'cn below: CH,
(d) and H,C-CHBr-C,H,
2A fi) !.\C1, ntF (a) ( A) - (11). (B ) • (I). (C) • (IV). (D ) • ( Ill)
(ii)Mnbyl~ (b) ( A) -(111). ( B) · (IV). (C) • (I). ( D)-(11)
(iii)ll,Oll-1
(<) (A)-(11). (B) -( IV). (C). (I). (D ) . ( Ill)
(d) (A)-(111). ( B) · (I). (C)-(I V). (D)-( 11)

1.6'' Y
c 1 a c11,ci
"A'canbc 125 Jun<. 2022 (Sblft-11)1 (t') >
J6. Whal is A in lhc: following reaction?
1,1N.£.'N
h1101r A
(a) lknzy) bromide ✓,; CH,
hu l C ) " ~ Major Product (b) Bromobcnzcnc
ll\l ll1.N1
(c) Cyclohcxyl bromide ,., ~f.0 CH, , c10
C(",•· ~
c 11,, & C1
~r (d) Methyl bromide
The major producl o f the above reaction is
Cl A
124 JuD<. 2122 (Sbift-1)1

. T~~
( MIJW P'Nduc11

, ,.,l__~
OCH,

,. a "'·",&",Y"
JJ. p
II:<) (Ma;ior Productl 127 Joly. 2021 (S.ift-11)1

( a)

NH,
Cons ider the ab<)\'c rcactK>n. the number o f
present in the product is _ _ . ·r·
1t electrons

124 Jun<. 2022 (Sblft-11)1

(a)
cr
~
Cll1 NII:

34. G iven bclo .,_,, arc 1wo stalrnxnts:

SlalHIHI I: Cll,OH and AgCN both can gcncralc
nuclcophilc.
(b) c!NIHll,-0 >CI O C I I,
Cl-11

OCH, Stat~mnt II : KCN and AgCN both will generate nilrilc 0

J
nuclcophilc with all reactio n conditions.

'"°i"
C1lOOSC the m ost approprialc o ption: JI. The product fonncd in the first step of the rcac1ion of
(b) 111 M1rrb. 2021 (Sblft•ll)I Br
(a) Both statcmmt I a nd statement II arc false. I
I NH, C~I - CH.: - ~ H - CH: - ) H1 - CH1 with excess Mg/Et:O
(b) Statement I is false but s ta tement II is true.
~ ClhOI I (Et • C:11,) 1s: Br
(c) Both statcmml I and ~'1atcmmt II arc true.
12' Frb, 2021 (Shin-1)1
(d) Stalcmcnl I is true but statement II is false. •d)v

21
20

44. The major producl (A) formed in the reaction gi,·cn below 46. The major product in the following rcaclion is:
11,C - CH - 11 - c 11, - H - CH,
(a)
1 1 127 Aua- 202 1 (Sbift-11)1 I
~
H,C - CH - CH: - CH - CH: - C H,
CH,-CII©
. 11-Cll,- Br , ,.,l
. T.,l. . 110,
_,,c 11,
lb) CH, - CH, I . + CHi~ a t,OH A IJ S.pl. 2020 (ShlR-11)1
CH - CH1
0 ( Major Prodoe1)
(a ) ~ (b) K
CH, - CH, -
(c )
111 - CH, - , II - CH, (a) (iv) < (i) < (iii) < (ii)
CH1 - CH: - CH - CH: - CH - CH 1

rgBr
(b) (i\') < (iii) < (ii) < (i)
(t') (i) < (ii) < (iii) < (iv)
(c))y- Ot-Bu

(d) x

(d) CH,CH, - CH - CH, - (d) (i\') < (i) < (ii) < (iii) 47. The decreasing order of rcacti\'ity orthe following o rganic
111 - CH,
MgBr
42. The corrttt decreasing order of densities of lhc following molecules 1owards AgN03 solulion is
compounds is: I' S<p1. 2020 (Shift-I)I
39. Presence of which rcagcn1 will affeel the rc,•cnibility
of the following n:action, and change it to a irrc\'crsiblc
reaction:

C H4 + I: ...:,.., CHJI + HI 127 J■ly, 202 1 (Slaift-1)1

(•) O (b ) v
r-7'YCI
(A) l..
Cl
(B)A Cl

OM c
(a) IIOCI CH,-CH
.-C
OH-CH,Br
~ (C) Cll,IHCH, (D) CH,THCH, NO,
(h) Liquid Nll 1
Cl Cl
(t') dilute HNO: (c) (a) ( B) > ( A) > (C) > (D) (b) (A )> (B) > (D ) > (C)
(d) Concentrated HI0 1 (c) ( A) > (B) > (C) > (D) (d) (C) > (D) > (A) > (B )
(c)~ (d)~
40. What is the majo r product formed by HI o n rcadion with 41. The mechanism of Ss I reaction is gi\'cn as:
H,
' c,,-Cll_.CH;I ~ Cl 0

"'rn,~"©'
~ Cl 0 0 0 0
H,C R- X - R x0 - R II x X.. R- Y + x
125 July. 2021 (Sbift-11)1 Ion pan Soh·ml
l·l , c / tH, . Sqw.ttdioo
12' t·<b. 202 1 (SblR-1)I
(a) (C) > (B) > (A) > (D) (b) (A) > (B) > (C) > (D)
"'"
CH, -
1'-" 11 - CH ,
(c) (D) > (C) > (B) > (A) (d) (C) > (D) > (A) > (B) A student wri1cs b-cncnl ch.arac1cristics based on 1hc given
mcchan;sm as: IJ s.p,. 2020 (ShlR-1)1
(a)
11 '3. The major producl of lhc following rcaclion is
45. Cons ider !he: reaction sequence gi,•cn below: (A) The reaction is rnoured by weak nuclcophilcs.

&
CH, I (8) R would be easily formed if 1hc substi1ucn1s arc

r
1-
I
N.otl
C :11,0 11 I
.
MaJOr Producl
7"Br~
ll:O
-- Oli + s,S
ralc - k(l•BuBr) ·· .( 1) bulky.
( C) The m1ctio n is accompanied by rBCemization.

~ ~ + 110 ll + Br"
(b) CH, - 11 - CH,

I
1
CH, IJI Aua. 2021 (Sblft-11 )1
(0) The reaction is ra,•ourcd by non-polar solvents.
Which obscn'tttions arc COITCCI?
C:l~OII H:C ra~ ~ • k(l•Bu8rl{Ol-l (3 ... (2 )
(a) (B) and (D) (b) (A ). (B) and (C)
(<) Cll, - I H - y H - CH, - CH,

.&PH a ()<:H
,
Which of the following statements is true? (c) ( A) and (C) (d) (A ) and (B)
CH1 I (a) Changing the concentration of base will have no 49. Among lhc following compounds. whic h o ne has the

(d) CH, -
r
1-1 11 - CH,I
(a) (b)
II
effect on m.ction (2)
(b ) Changing the concentration o f base will ha\'e no
effect on reaction ( I )
shoncs1 C - Cl bond?

H,Ct
(a ) H 1C Cl
I' S.p1. 2020 (ShlR-11)1

(b) TH
_,..Cl

CH 1 H (c ) Changing the base from OH 10 OR will ha,·c no H, CH,

CH1
effect on reaction (2)
H~
41. The corrccl order of the following compounds showing
increasing tendency towards nuclcophilic subslitution (c) (d) CH, (d) Doubling the concentration of base will double the (d) 1 -I
rate of both the reactions 12 SrpL lt20 (Slaift-11)1 CH,
n:aclion is: 124 t"tb, 202 1 (Slaift•ll>I

23
22
 IJ. Cons ider the following reaction that goes from A to B in 16. Identify the co rrect order for the given property for
7. Excess of isobulanc on reaction wi1h Br: in presence of hydrolysis increases. thccc steps as shown below, (6 April. 2023 (Sllift-11)1 following compounds 129 Jan, 2023 (Shift-I )I
lighl at I 25°C gives which one of 1hc following. as lhc Reaso■ (R): J- is a good nuclcophile as well as a good

-~ .
lca\'lng group. (A)Boiling Point: ............... Cl </"'-,./CJ< ~ Cl
major product? 126Aug. 2021 (Sllift-1)1
In the light of the abo\'c statements. choose the correct
IHJ an.l>"wer from the options gi\'cn below. (B) 0cns;iy, -------... B, < /°'v'CI <-------... I

(a) CH1 - ~ H - CH1Br (b) CH, - TH - B, (24 Joa. 2023 (S•m-1)1 Br Br

~~r
(a) (A) is false bul ( R) is true.
II Ill
CH: Br CH, (b) (A) is true but (R) is falsc. (C) BoilingPoint: ............... Br<Ae,<
e, (C') B01h (A) and (R) arc true and (R) is the co rrcel Reaction Coordinate
I explanatK>n of(A). (D )Density: / ' ( I < /"'-,./B r < /'( Cl
(c) CHJ -f H - CH:Br <di c11, - T- c11,- e, (d) Both (A) and (R) are true bu1 (R) is NOT the eoncc1
Choose the COrTect
Numbt:r or N■ mMror Rar. Br Br
explanatK>n of(A).
CH1 CH, intumNiatn AdintN drtumiai■g
(E) Boiling Point: ~ Cl > ~ Cl > ~C l
11. Dcc:reasing order 1owards S,.. I reaction for the following comp&u:n lltp
Physical and Chemical Properties of compounds is: (a) II Choose 1he correct answer from the option given belo w:
Haloalkanes and Haloarenes (b) II (a) ( B). (C) and (D) only (b) (A). (C) and (E) only
(c) (c) (A). (C) and ( D) only (d) (A ). ( B ) and (E) o nly
8. The graph which represents the following reaction is:
(d) Ill 17. Co mpound from 1hc following 1hat will nol produce

. ··c . -~
(c. H, )1 C-CI ,:_. (C, H1 ) 1 C-OH
prccipiuuc on ruction with AgNO1 is:
11 t·tb. 2023 (Shift-11)1 !4. ~ Cl ~ ~Nu (I)
(II April. 2023 (Shift-II )(

(a) (b ) I<) (d) M~ OMe~ r'JrB,

l•l v
IJO JH. 2023 (Shift-11)1
N Cl ~ , O " 'N• (II)
(a) (1) > I<) > (d) > (bl ib) (1) > (b) > (<) > id)
o,N o,N ~.,,,e,
(h) ~

,,·-~ . -lL
l<C,11,1,C-OI (Oll7 (c) (b) > (d) > (c) > (•) (d) (d) > (b) > (c) > (• )
Where Nu • Nudcophilc
12. Choose the halogen which is most rcacti\'e towards S~
Find oul the con-eel sta1cmcn1 from the op1ions gi\·cn
reac1ion in the gi\'en compounds(A. B. C & 0)
11 ApriL 2023 1s•m-11I
belo w for lhc abo\'C 2 reactio ns. (c) [:>-er
(II April. 2023 (Shin-1)1

(IC, H,J,C- 01 IPyridine(

9. The compound which will have the lowest nue 1owards
A
.cn:,., (a) Reaction (I) is of 2.,. o rder and reaction ( II) is of I '"
order
(b) Reaclion ( I) and (II) bolh a rc o f 2... Of'der
(d) @- CH• CH-Cl-1,- B,

18. The correct order of rcac1ivi1y of following haloarcncs

(c) Rcaclion (I) is o f I" o rder and reaction (II ) is of 2.,.
nuclcophilic a.romntic subslilutio n on trcalmml with OH o rder towards nuclcophilic substitulion w ith aqueous NaOl-1 is:
is (25 Jon. l02J (S.lft-1)1 (d) Reactions (I) and (II) bolh arc of I'" o rder (8April. 2023 (Shin-II )(
(b)l.,,, 15. 2-Mcthyl propyl bromide reacts with C :H,O and gi\•cs r;:::::;yc1 ~ Cl
(a) ~
9 NO,
•A' whereas on rcac1ion wi1h C:H,OH it gives ·e·. Thc
mechanism followed in 1hcsc reactions and the products
• A" and ' B' rcspccti,•cly arc, (IJ ApriL2023 (ShiR-1)1
(A) ~ (B) l U I

NO, N01 (a) s ,...2. A • iso-butyl c1hyl e ther: s,. I. B • tert-butyl Cl

17/30
c1hyl ether
le) .X.~ (d) f (b) S,.. I. A • 1cn-butyl ethyl e ther: Ss l. B • 2-butyl ethyl
(C) (D) ~
(QJ NO, (a) A-Br1, 1 : B-1(••: C-Br0 , 1 ; D-Br1. , elhcr
OMc O, N NO,
CQlNO, (b) A-Br10, ; B-1,., : C-Brn, 1 : D-Br,. , (c ) S,.. I. A • tcrt-butyl ethyl ether: S,..2. B • isobutyl ethyl Choose !he corrccl answer fro m the op1ions given below:
(C') A-Brl~I: B- 11., : c~e,l•I: D-Br••• elher
(a ) A > B > D > C (b) C > A > D > B
10. Assutlon (A): Hydrolysis of an alkyl chlo ride is a (d) S, 2. A • 2-butyl cthyl c<hcr. S, 2. B • lsobutyl cthyl
slow reaction but in the presence of Nat. 1hc rale of the (d) A-Br1• 1 : B-11• 1 : C-Br10 1 : D-Br1• 1 (c) O > C > B > A (d) O > B > A > C
ether

16
17

9. Match list-I w ith list-II 22. For the reaction: 2◄. Number of moles ofAgCI formed in the folk>wing reaclion 21. Which one: of the following compow,ds is inactive towarcb
is (24J10. 2023 (Shift-I)(
1- Bromopropane is reacted w ith reagents in List-I 10 give ROl: Br + I ~ ROt: l + Br Ss l reaction? (28 J•••• 2022 (Shlft-1)1
produc t in List-II The con-ecl Slalcment is :

List-I - RHgtat List-II • Prod■d

(6 Apri~ 2023 (Shift-I)(
(a) Tbc transition state formed in the above reaction is
(A) KOll(ak) (I) Nitrilc
less polar than the localised anion.
{B) KCN(ak) (11) Ester (b) ~ CI
(b) The reaction can occ ur in acetic acid also. ZS. Considering the below reactions. the compound · A' and
(C) AgNO, (Ill) Alkcnc compound 'B". rcspccti\'ely arc: 129 July. 2022 (S11.ift-1)1
( c) Tbc solvent used in the reaction solvatcs the io ns
(D) H,CCOOAg (IV) Nitroalkanc formed in rate dc:tennining step. ·A· ~ .,.............a ~ ·e·
I MaJOI' P'rodw:tf C:fl)Oll- 11:0 C:fl10 11-llp CM -,.. P'rod,otO
(IJ ApriL 20ZJ (Shift- II)( (d) Br can act as competing nucleophilc. (c) ~
(a ) /'-..~ • ~ - /'-..~ • ~
Cl
(a) (A) - ( IV), (B) - (Ill). (C) - (II). {D) - (I) 2J. Identify the COfTC'Ct order of reactivity for the following (b) /'--..c ■ N. /'-..c ■ N
pairs towards the rcspccti\'e mechanism
(b) (A) - ( Ill). (B) - (I). (C) - (IV). (D) - (II)
(10 Apri~ 2023 (Shin-1)1 (c) ~ ■ 8. /'-..c ■ N HJC' c- c1
(c) (A) - ( I). (B) - (II). (C) - ( Ill). (D) - (IV) <di /'-..c • N. /'-..~ • ~ (d) a ~

(d) (A) . (I). (B) - (Ill). (C) - (IV). (D) . (11) 26. Com pound · A' underg oes follo wing seque nce o f
reactions 10 gi\'e compound ·s·. The eorrcct struclurc
O. The mnjor product formed in the Friedel-Craft acylation and chirality of compound ·a· is (where E1 is - C: H, ) 29. (A) i'~:: ·"
to• IH,O H"
4-Bromophcnyl acetic acid.

Br
of chlorobcnzcnc is. ( 15 Apri~ 2023 (Shift-I)( (29 Joly. 2022 (S.ift-11 )(
In the abo\'e reaction (A) is 121 Junt-. 2022 (Shin-11)1

,,, ~rn,
Cl

(b) © :COC:11 ,
(B) S, 1
.
B,
>
1/

~"' I Compound 'A'

(i )Mg.Et ,O B
(ii)O,O
,.,¢
COCII ,

(C) Electrophilic subs1i1utio n

(a)
>-<D Achiral

(h) 6
CH,CH,

B,

(b)
>-<o· c hiral

Br'OI ¢B,I
(c)
>-<o· chiral (c)

B,O -&
CH,

CH• CH,

O
---.._ /'-.... _,,,OD
(D) Nuclcophilic subs1i1utio n < (d) __,,.,- ~ . Achiral (d)
Ch lorine is ortho/para directing. para is major.
"' "' 27. The majOf' product in the reaction..
Br
I . The isomeric dcutcratcd bromide with molecular formula NO, CH 1 CH 1 JO. Two isomers (A)and ( B) wilh molar mass 184 g/mo l and
C~H~DBr having two c hiral carbon atoms is I , - I elemental composilio n C. 52.2% : H. 4.9% and Br 42.9°'11
Choose the corrttt answer from the options given below: C H1- y-e1+ K ~ -CH1 ----f' ? is ga \'c bcnzoic acid and p-bromobcnzoic acid. rcspcctivcl)I
(25 JH. Z02J (Shift-II)(
CH 1 CH 1 o n oxidation with KMnO,. Isomer 'A" is optically aclivc
(a) 2-Bromo-1-dcutcrobutanc (a) (A). {B) and (D) only
and gi\'CS a pale yellow precipitate when warmed with
(25 J ■... 2022 (Shift-I)(
(b) 2-Bromo-2-deutcrobutane (b) (A). (B). (C) and (D) alcoholic Ag NOy Isomer' A' and •B' arc, respectively
(a) I- Butyl ethyl cthcr (b) 2. 2 - Dimcthylbutanc (29 Jun<. 2022 (Shifl-11)1
(c) 2-Bromo-3-deutcrobulanc (c ) (A). (C) and (D) only
(c) 2-Mc thylpcnt- 1-<n<: (d) 2-Mcthylprop-l -<ne
(d) 2-Bromo-1-dcutero-2-methylpropanc
(d) {B). (C ) and ( D) only

19
18
 21. A compound 'A' fonnula ofC1H£ h on reaction with
18. 1be COITCCI reactivi1y order of alcohols 1owards H- X alkali can give '8 ' of formula C 1Ht,O o r 'C' of formula
(c) CH, - 1H -O
1~ ~zooof::~owmg-n ~ will be C:ilL. 'B' on oxidation gave a compound of lhe

y . . .,.__..
C,11.
(IJ CH., : CH - OH formula C1Ht.01. 'C' with dilute H 2S0, containing

(d) CH, - ? -CI

T"· OH Hg 2• ion gave 'D' of formula C1 H.sO. which with
bromine and alkali gave the sodium salt of CitLOi.
( II) H,c - - ( ,
CH, CH,
Then 'A ' is
NO, (a) CH,CH_.CHCI,
( Ill) CH., - CH., - OH

""q',
14. Tbt: produa formed in the reaction (b) CH,CO ,CH,
H,C
ql'h H OH (Iv) CH, - fH- CH3 (c) CH,CICH,CH,CI
'S:: F
~ +SOCl 1 ➔ is: OH (d ) CH.,CHCICH,CI
00

NO,
H
NO, (a) c¾ (b)
2'11
(a) ll>l>Ill>IV (b) IV > Ill> ll>I
(c) Il > IV > l > III ( d) ll>IV > Ill> I
21. lsobutyl magnesium bromide with dry ether and
absolute alcohol gives
CH, -r-.CH20H and CH,CH,MgBr
H,C
Q 'SPh H,C
Q [Ph H ~ - CI H~SO,H
19. Identify ·z· in the foUowing reaction series. (a)
'S:: SPh (c) (d) CH, CH,c:H,Br
(cl (d) CH3
H H ~ .NaOH (X ) ~( Y ) ~ (Z ):
(bl CH, -r-.CH 2 -CH 2CH3 and

NO, NO,
15. lbc: reaction (a) Mixiun, of CH, -ci:" - f 11 2
CH3
~u · soc,, ~ {'a ·so .©l, Cl OH Mg (OH) Br

11. In the n,oction O oCH, ~ the

1
Proc«ds by the mechanism
II
and CH,-f"T "' (cl CH3-r-.CH3.
( a) (b) SN~
OH OH
SN, CH 3
product arc
(C) s,, (d) S E,
(bl CH3-ci:"-'f"i 0! 2 = 0! 2 and Mg(OH)Br
(al Br-OOCH, and H, OH Cl (d ) CH3-r-.CH3 wid CH,CH,OMgBr
16. Which one of the foUo wing compounds most readily (c) CH3- 0I - f H2
undergoes substilution by Ss , mechanis m? CH3
CI OH
(b) OBrandCH3Br
11,c-f.
CH,
(d) CH3 - <r" - 'r"' 23. Following reaction is
Cl Cl II H
(a) )
(c) O B r andCH,OH
Cl
20. Which of the following undergoes hydrolysis most
CH,(Cll ,),) ' gH
'<(CH,),CH,
C-llr --=->+ HO- C
(b) 11,C\ H,C CH,
ea.-.ily
(d) 0 0 1 1 andCH,Br

(c)
CI
Cl
(a)
~o
l,'.::::)
Cl
(a)

(c )
E1
E,
12. Ir un alkyl halide CH.iCH.<:HiX goes for H,C- <
C,11,
dchydrohalogcnation followed by addition of HX
will lead 10 formation of
(a) Same alkyl halide (d)
H,~ H,
(b )
~o
~
Cl
24. Consider the following anions,
0 0
H,C Cl II II
(b) Diffcrcn1 Compounds
(c) An isomer
NO,
CF:, - n-o- C6 H, - fl -o-
(d) An hydrocarbon 17. Fo r the reaction ) § CCI 0 O
~ Cll, - Cll = Ol - 0 1, (c)
( I)
Cll,CIIIXICll ,CII, ~ ( II)
JJ. Which one o f the following compounds mosl readily
cu,= a1 - cn,- c11, NO, NO,
undergoes substi1ution by Sl'I, mechanism?
(a) CH, - CH=CH - CH, predominates 0
\H,

k" II
(b) Cll1 = CH- CH1 - CI-I, predominates
(a) CII, - CH- CH,CI
(c) Both arc f ~ in equal amounts
CH3 - C - o-
(d)
(b) CH,CH,0
(d ) The product ratio depends on the halogen (IV)
NO, NO,
11

When attached to sp 3- hybridized carbon. 1heir (i) How many compounds give Ss2 reaction on
leaving group abili1y in nuclcophilic subs1i1ution trcatmcnl wi1h NaSH?
(o) (A)· (II). (BJ· (I). (C). (III). ( DJ . (IV)
reaclion.1/i decreases in the o rder (ii) How many compounds give E: reaction on
(b) (A) · (III). ( B ) • (II). (C). (IV). (D). (I )
(a) l> l l> Ill> IV treatment with alcoholic KOH?
(b) l > l l> IV > lll (iii) How many compounds do not react under either
Classification & Nomenclature of (<) (A) · (IV). (8) · (II). (C). (III). (D ). (I)
(c) IV > l > Il > III of the previous reaction conditio ns? Haloalkanes and Haloarenes (d) (A )· (II). (BJ· (I). (C). (IV). (0). (III )
(d) IV > Ill> l l> I
I . Mu imum number of isomeric monochloro dcrivati\"cs !Ii. In the following given reaction ' A' is

INTEGER TYPE QUESTIONS

29. How many substrates will show rearrangement during
Ssl reaction':'
w hich can be obtained from 2.2.5.5tetramcthy lhcxanc by
chlorination is _ _ _ _ . 124 JH, 202J (Sllift-11)1
yH,

---y·'J·~-c:t
c-c11.
25.
Cl - ~ -
0
OC.,H
5
tl)'Y 'RMsX
3° Alcohol. 2. The IUPAC name of cthy lidcnc chloride is :
125 J ■■•. 2122 (Slllft-1)1
d + .Her - ·~·
•
Find oul value of · y •
f',,1 i40
I Br Cl (a) l-Chloroc1hcnc
(C') 1.2-Dichlorcthanc
(b) 1-Chlorocthync
(d) 1.1.-Dichlorcthanc
m&JOr
product
X,,-Br Br .,,..___.,l
26. Find oul number of possib~ E1 products from V ·O" ·LJ - c 1. J. Whal is the IUPAC name of the following compound'! 124 Jaa, 202J (Sblh- 1)1

following reaction. CH,K

l J
"'H
,X.,,..___,,,CH,0H
- - T ----;r--+ ~ c 1.( ( C l .6 H '
Br CH15 Br
JO. Fmd out number of reactions those proceed with 110 Jao, 2119 (Shift-11)1
27. Identify number of substrate those can given Ss l and
retention of configuration. (a) J-Bromo- 1.2-dimcthylbtu -I-enc
SN2 reaction both. CH,
CH3 (b) 3-Br ~ J-mcthyl- 1.2-dimc1hylprop- l-cnc

0 -c H,-Br, H3C+
- CH,
Br.
H3C
-5:' . Br
(i) PhkH.ill!tl.+
Br
(C') 2-Bromo-3-mcthylpcnt-3-cne
(d) 4-Bromo-3-mcthylpcnt-2-cne

CH1 Methods of Preparation of

11,c~
Ph
.
H,C
~ c1-~.r\r
y ~
I
(ii) P h ~ I _____.__..

Br
--1 ll1111t,O
Haloalkanes and Haloarenes
4. Match L ist,! with List-II

6.6,
CH3
Usl-1 Usl-11
(ii)PhkH~ 6. Choose the correct statement regarding the formation of
CH,- CH, - CI . ~ CI carbocations A and B g ivcn.117 Mart"h. 2021 (Shlft-11)1

Ph
Br (A) ~-CH,C>_,,_,@ (I) Fittig 1'C21Clion
11,C-CII,-CH, ! H. + &r
28. Examine the ten structures shown below and select
those that satisfy each of the follo wing condition.
(iv) o +c1....fil1!..+ H C- CH:- CH~ Hi + HBr
1
. .,_: .

CH3 H Wurtz Finig {

(BJ ~ +2Na-,@-@ (II) reac1ion '" CH + e
H1C- C H1-CH- Br
<•> O'Br
A
(b) H,C+ CI 1
·o·
CH, (a) Carbocation A is more stable and fonncd relatively
alslowrale
(c) U B r (d) CH, - 1
( b) Carbocation B is more stable and formed relatively
at faster rate
(c) VBr (I) VCI
(c) Carbocation B is more stable and fanned relatively
(D) Cil,CI + Nal ➔ C:H,I + NaCl ( IV) ~:;::ycr al slow rale
(g) x.,..c1 (h) " Y 'CI (d) Carbocation A is mo re stable and formed relatively
Cl IJO Jaa, 212J (S hift-1)1 al faster rale

(i) CFBr G>

cb ,. 15
 JJ. Give the o rder of decreasing reactivily towards an 38. Which one of the following compound is most reactive

6I,_6'.0.6CI
25. Which or the following compounds will show raster electrophile. towards Ss-2 displacemeru~

L
,.,9 ,. 9,,,9 ,.9 ¥1'a """'.: '_,.,
bimoleculaI SsAr reaction?
(a) CH,CH,CH,CH,-<:I
29.
lb) (CHi,C-<:I
( c) (CH1 ),CH-CH-CH1

NO: NO: NO: NO:

a
The product is (I) (2) ()) (4) . !1
1•16
(a) I > 2 > 3 > 4 (b) 4 > I > 3 > 2 i<n (CH1 ),Clt-<:H,-<:I
26. II~118, 0
tAL ~ I I
~(Bl
.... (c) 3 > 4 > I > 2 (d) 3 > 2 > 4 > I
34. Which or 1hc following organic chlorides "'' ill not give a
39. Which ofthe foUowing compound will undergo Ei climina1ioo
n:adily'
~Cl Friedel.Craft alkylauon product when healed wnh benzene Cl
Cttp ll H1 andAICI,?
The produclS (A) and (B) Me respectively
OE, O E1 ~I 11,0
NO. (a) (CH1) 1C-<:I (al \::::1- J-<:,H, ---'---'
(bi C11, • C11C11,-<:I
(a)
~011
& ~OIi

1.n~., (c) c 11,rn,-<:1

(d) C"!-11-CI
@
f'
I
Cl 35. Which of lhe following stalemcnl docs not correelly
& ~OIi describe E 1 reactions of alkyl halides (RX)?
JI. Ease or t0n1zauon 10 produce carbocatt0n and bromide ton
(a) Rearrangcmcn1 1s possible.
(bi ' under the 1rea1mcn1 of AS- will be ma:umum in:
(bi lla1c • klBasellRXI
o,
(c) Rate • k IRXj
o .-111e,
o/°"
,n

:-~~,~, ,. f
(d) The reaction occurs m two or more d1st1nct steps. c ,11,0
1
lei
& ~"' 36. Wh1ch ofthe-followmg alkyl hahde 1s most reac11ve towards ~ Cit,

48. Select the concct one among the following statements:

Cll:Br u,
(a) ............... Br will react less readily than
(<n~H, & ~·,
X ' e r for f:.2 reaction.
(b) ...............Cl will react more readily than ............... Br

a:
Cll: Hr OCll1
27. ldenlify lhc rcactanll(X) and (Y) fo.- the following reaction. Cl CH.1 for Ss1 ruc1ion.
rcspccllvely.
(X)
Alkyl halide Alkync
(Y) ~

(a) Cl·l 1(Cl-l 2 )~CH 2 - Cl • C H 1 - C ■ CH

4- Dccyne

(b) Cl·IJ(Cl·l2) 2CH2 - Cl + Cl·l1 - (Cll 2 )2 - C • CH

JI. liKI,, p

The product P wlll be:

, ,©-' ~ ~- (c) 0 - B r w,11 react more rcad,ly than

O -c 11,er fo, Ss2 rcact;on.

(c) Cl·IJ(Cl·l2 )2CH2 - CI + CH1(Cl·l2 ) 1- C • CH OCIIJ
(d) Cl-11- CH2- CH2 -CI + Cl-11 (Cll 2 )• - C • CH (b) ® 2SbCI,

X ;:~
37. The maJor product or rollowing reaction lS
(d) ..............., w ill rcacl more readily than >-1 towards
28. Which or the following compound give ras1es1 Ss 2Ar
rcaclion'! S:r,,..2 reaction.

(a)6 (d) ~h xtureof(a)&(b) Producl

Br
o ·
© ( N H,

J2. Which of the following reagenl is bcsl when Fricdel-craf\

(a)Y' Br
ib)Q
.. ,. s.su.
hq.NII ,

¥
~
Alkylat1on lakes place?
(al HO·
(bl AICl1 (anhyd.)
" OH
0 11
lllc reac1ion is
(a) ArSs l

c5
(c ) NO, NO, NOH (bi M i,,-2
(c) AICl1 (hydrated) (c) Nuclrophilic substitution via bcnzync mechanism

NO:
(d) All of these
(c) l<n Y (d) None of lhcsc

ER TYPE QUESTIONS 44. The total number ofalkcncs possible by dchydrobromi

of 3-bromo-3-mclhylhcxane using alcoholic KOH is F-@-No (CH,),NH
w many s ubstances s how rearrangement during Ss I 7.
' DMF
ction? 45. Rearrangement o f carbon skeleton o f substrate is pc SINGLE CORRECT TYPE QUESTIONS H , /C.-al)1K" RcdK,IOII
in how many of the following reactions'! (A) (Pi
Br I. During dcbrominaoon of meso-2.3-dibromohnane.

~Br

a)
6 <)+-c1
(b) (c)
EAS ( Electrophilic aromatic substitution). electro
addition on alkcnes. free radical substitution of alkar
S, I. S,.2. E1• E,. E 1cB, S,2Ar
'4. How many diffe rent i somers of alkenes (inc l
stcrcoisomcrs ) upon catalytic hydrogenation adds om
with Zn wst/CHj{X)OH the major compound f ~

(a)
;,
n-butane
(cl cis--2-blllcne
(b) I-butene
(d) tJam:-2--butcne
(a)

(bl
O,N- @ -NH,

H,C

H,C
-@-
)N Q NH,

of H2 to give the same product 2. 2, 3. 5-tenramet.hyl ht: 2. Bcnzyl chloride (c.H,CH.-0) c-.-, be prq,arcd from H,C -@-
toluene by chJorinalion with
)N Q NH,
;:YBr 47. If 3-bromo-4-mcthyl hexane is treated with cthanolic (c) H,C
(a) SO,CI, (bl SOCI,
solution. how many d ifferent alkcncs would be form. I
(c) PCI, (d) NaOCI NH,
CH, 48. Consider the following reaction.

.6.
H,C -@-
)N Q NO,
~
(d) (e) J. A solution of(+) 2-chloro-2•phcnylcthane in 1olucnc (di
+ HBr(cxcess) raccmiscs slowly in the prcscncc of small amoun1 of H,C

-( ~ Br How many dilfcrent products would be fonned?

SbCl, cklc IO the formation of
(a) Carbanion (b) Caibcnc I. The reagent (s) for the following '-"'Onvcr..ion:
-H-<Br
I Br .,
(/) (g) (h)
49. Consider the following reaction and the major produ (C) F~-radical id) c.rtJocatioo
"A Br
~ HC ■ Olis
4. asymmetric carbon of a

?
~ + HCI - - - + ~ An SN! reaction al Wl (a) alcoholic KOH
Cl ccmpound always gives :
(bl Alcohol;c KOH followod by NaNH,
(cl aqucsous KOH followed by NaNH,
If energy profile of the above reaction is drawn, how (a) an enartiomer or the subslrale
(d) ZnlCH,OH
transition stales would be observed? (b) a pnxb:1 with opposi1e opcical rotation
Br 9. The following compound on hydrolysis in aqucou.,;
50. If a raccmic mixture of J •mcthyl- l •pcntene is trcatc- (C) a mixture ofdwacn:omcn
i) acetone will gi\'C:
HCI. how many different chloropcntane ( imponant pn (d) a single sicrcoisomcr CH, II CH,
long the following, X is the number of elcctrophilcs and only) would be fonncd?
s the number of nuclcophiles. Repon your answer as 5. The nwnbcr of isomer for the compound with McO- o t - t - t o - NO,
ill molecular formula CzBrO Fl is •
H Cl CH,
(ii) I - la) J (b) 4
CH~ Cl-I, H CII,
(c) 5 (di 6
NO~ (iv) ~ H1 (K)McO- o t - t - t o -NO,
(,·i) 8 ... 6. ldcntiry the .set of rcagcnt5.lrcaction oonditiom ·x· and
NH, II OH CH,
'Y' in the following .!id of tr.m'ifonnatiom CH, H CH,
~I (,,iii) H'

.
CH,-CH:-CH:Br_y...,. Prodoct~CH, --fH-CH,
AICl 1 (x) CH1 0fl ill McO- o t - t - t o -NO,
B,
(a) X = dilu1e aqueous NaOH. 20'C. Y= HBr/acctic OH H CH,
CH,- C= O (xii) BH1
acid.20'C
CHJ H CHJ
(bl X = cona:ntralod alcohol;.; NaOll. 80°C; Y =
HBr/acctic acid 20° (M)McO- o t - t - t o - NO,
(c) X = dilute aqueous NaOH 'ltf'. Y = Bn/CH0.1.
O"C H CH, OH
(di X = concentra1od alcoholic NaOH. 80°C; Y " h mainly gives
{a) K and L only (b) K only
BriCHCh. OOC
(c) LandM only (di M only
II
 JJ. Give the o rder of decreasing reactivily towards an 38. Which one of the following compound is most reactive

6I,_6'.0.6CI
25. Which or the following compounds will show raster electrophile. towards Ss-2 displacemeru~

L
,.,9 ,. 9,,,9 ,.9 ¥1'a """'.: '_,.,
bimoleculaI SsAr reaction?
(a) CH,CH,CH,CH,-<:I
29.
lb) (CHi,C-<:I
( c) (CH1 ),CH-CH-CH1

NO: NO: NO: NO:

a
The product is (I) (2) ()) (4) . !1
1•16
(a) I > 2 > 3 > 4 (b) 4 > I > 3 > 2 i<n (CH1 ),Clt-<:H,-<:I
26. II~118, 0
tAL ~ I I
~(Bl
.... (c) 3 > 4 > I > 2 (d) 3 > 2 > 4 > I
34. Which or 1hc following organic chlorides "'' ill not give a
39. Which ofthe foUowing compound will undergo Ei climina1ioo
n:adily'
~Cl Friedel.Craft alkylauon product when healed wnh benzene Cl
Cttp ll H1 andAICI,?
The produclS (A) and (B) Me respectively
OE, O E1 ~I 11,0
NO. (a) (CH1) 1C-<:I (al \::::1- J-<:,H, ---'---'
(bi C11, • C11C11,-<:I
(a)
~011
& ~OIi

1.n~., (c) c 11,rn,-<:1

(d) C"!-11-CI
@
f'
I
Cl 35. Which of lhe following stalemcnl docs not correelly
& ~OIi describe E 1 reactions of alkyl halides (RX)?
JI. Ease or t0n1zauon 10 produce carbocatt0n and bromide ton
(a) Rearrangcmcn1 1s possible.
(bi ' under the 1rea1mcn1 of AS- will be ma:umum in:
(bi lla1c • klBasellRXI
o,
(c) Rate • k IRXj
o .-111e,
o/°"
,n

:-~~,~, ,. f
(d) The reaction occurs m two or more d1st1nct steps. c ,11,0
1
lei
& ~"' 36. Wh1ch ofthe-followmg alkyl hahde 1s most reac11ve towards ~ Cit,

48. Select the concct one among the following statements:

Cll:Br u,
(a) ............... Br will react less readily than
(<n~H, & ~·,
X ' e r for f:.2 reaction.
(b) ...............Cl will react more readily than ............... Br

a:
Cll: Hr OCll1
27. ldenlify lhc rcactanll(X) and (Y) fo.- the following reaction. Cl CH.1 for Ss1 ruc1ion.
rcspccllvely.
(X)
Alkyl halide Alkync
(Y) ~

(a) Cl·l 1(Cl-l 2 )~CH 2 - Cl • C H 1 - C ■ CH

4- Dccyne

(b) Cl·IJ(Cl·l2) 2CH2 - Cl + Cl·l1 - (Cll 2 )2 - C • CH

JI. liKI,, p

The product P wlll be:

, ,©-' ~ ~- (c) 0 - B r w,11 react more rcad,ly than

O -c 11,er fo, Ss2 rcact;on.

(c) Cl·IJ(Cl·l2 )2CH2 - CI + CH1(Cl·l2 ) 1- C • CH OCIIJ
(d) Cl-11- CH2- CH2 -CI + Cl-11 (Cll 2 )• - C • CH (b) ® 2SbCI,

X ;:~
37. The maJor product or rollowing reaction lS
(d) ..............., w ill rcacl more readily than >-1 towards
28. Which or the following compound give ras1es1 Ss 2Ar
rcaclion'! S:r,,..2 reaction.

(a)6 (d) ~h xtureof(a)&(b) Producl

Br
o ·
© ( N H,

J2. Which of the following reagenl is bcsl when Fricdel-craf\

(a)Y' Br
ib)Q
.. ,. s.su.
hq.NII ,

¥
~
Alkylat1on lakes place?
(al HO·
(bl AICl1 (anhyd.)
" OH
0 11
lllc reac1ion is
(a) ArSs l

c5
(c ) NO, NO, NOH (bi M i,,-2
(c) AICl1 (hydrated) (c) Nuclrophilic substitution via bcnzync mechanism

NO:
(d) All of these
(c) l<n Y (d) None of lhcsc

ER TYPE QUESTIONS 44. The total number ofalkcncs possible by dchydrobromi

of 3-bromo-3-mclhylhcxane using alcoholic KOH is F-@-No (CH,),NH
w many s ubstances s how rearrangement during Ss I 7.
' DMF
ction? 45. Rearrangement o f carbon skeleton o f substrate is pc SINGLE CORRECT TYPE QUESTIONS H , /C.-al)1K" RcdK,IOII
in how many of the following reactions'! (A) (Pi
Br I. During dcbrominaoon of meso-2.3-dibromohnane.

~Br

a)
6 <)+-c1
(b) (c)
EAS ( Electrophilic aromatic substitution). electro
addition on alkcnes. free radical substitution of alkar
S, I. S,.2. E1• E,. E 1cB, S,2Ar
'4. How many diffe rent i somers of alkenes (inc l
stcrcoisomcrs ) upon catalytic hydrogenation adds om
with Zn wst/CHj{X)OH the major compound f ~

(a)
;,
n-butane
(cl cis--2-blllcne
(b) I-butene
(d) tJam:-2--butcne
(a)

(bl
O,N- @ -NH,

H,C

H,C
-@-
)N Q NH,

of H2 to give the same product 2. 2, 3. 5-tenramet.hyl ht: 2. Bcnzyl chloride (c.H,CH.-0) c-.-, be prq,arcd from H,C -@-
toluene by chJorinalion with
)N Q NH,
;:YBr 47. If 3-bromo-4-mcthyl hexane is treated with cthanolic (c) H,C
(a) SO,CI, (bl SOCI,
solution. how many d ifferent alkcncs would be form. I
(c) PCI, (d) NaOCI NH,
CH, 48. Consider the following reaction.

.6.
H,C -@-
)N Q NO,
~
(d) (e) J. A solution of(+) 2-chloro-2•phcnylcthane in 1olucnc (di
+ HBr(cxcess) raccmiscs slowly in the prcscncc of small amoun1 of H,C

-( ~ Br How many dilfcrent products would be fonned?

SbCl, cklc IO the formation of
(a) Carbanion (b) Caibcnc I. The reagent (s) for the following '-"'Onvcr..ion:
-H-<Br
I Br .,
(/) (g) (h)
49. Consider the following reaction and the major produ (C) F~-radical id) c.rtJocatioo
"A Br
~ HC ■ Olis
4. asymmetric carbon of a

?
~ + HCI - - - + ~ An SN! reaction al Wl (a) alcoholic KOH
Cl ccmpound always gives :
(bl Alcohol;c KOH followod by NaNH,
(cl aqucsous KOH followed by NaNH,
If energy profile of the above reaction is drawn, how (a) an enartiomer or the subslrale
(d) ZnlCH,OH
transition stales would be observed? (b) a pnxb:1 with opposi1e opcical rotation
Br 9. The following compound on hydrolysis in aqucou.,;
50. If a raccmic mixture of J •mcthyl- l •pcntene is trcatc- (C) a mixture ofdwacn:omcn
i) acetone will gi\'C:
HCI. how many different chloropcntane ( imponant pn (d) a single sicrcoisomcr CH, II CH,
long the following, X is the number of elcctrophilcs and only) would be fonncd?
s the number of nuclcophiles. Repon your answer as 5. The nwnbcr of isomer for the compound with McO- o t - t - t o - NO,
ill molecular formula CzBrO Fl is •
H Cl CH,
(ii) I - la) J (b) 4
CH~ Cl-I, H CII,
(c) 5 (di 6
NO~ (iv) ~ H1 (K)McO- o t - t - t o -NO,
(,·i) 8 ... 6. ldcntiry the .set of rcagcnt5.lrcaction oonditiom ·x· and
NH, II OH CH,
'Y' in the following .!id of tr.m'ifonnatiom CH, H CH,
~I (,,iii) H'

.
CH,-CH:-CH:Br_y...,. Prodoct~CH, --fH-CH,
AICl 1 (x) CH1 0fl ill McO- o t - t - t o -NO,
B,
(a) X = dilu1e aqueous NaOH. 20'C. Y= HBr/acctic OH H CH,
CH,- C= O (xii) BH1
acid.20'C
CHJ H CHJ
(bl X = cona:ntralod alcohol;.; NaOll. 80°C; Y =
HBr/acctic acid 20° (M)McO- o t - t - t o - NO,
(c) X = dilute aqueous NaOH 'ltf'. Y = Bn/CH0.1.
O"C H CH, OH
(di X = concentra1od alcoholic NaOH. 80°C; Y " h mainly gives
{a) K and L only (b) K only
BriCHCh. OOC
(c) LandM only (di M only
II
32. Arrange lhc following in decreasing order of stability of their 42. Elcctrophilc NO; anacks 1hc following
(d) © " C'=CH , ©"CE=C - C,H,

u . ~.u"·
transition state during elimination by a strong base:
· @ "cc1, I. When the concentralion of an alkyl 5/30...,
the concentration ofnuclcophile is rec. ,IC
37. 1-Phcnyl-2-chloropropune on lreatmcnt with alcoholic ofS:,,:I increases by:
I II Ill
caustic potnsh gives mainly to give rcfuct: (a) 3 tim(."S
(a) II > I > Ill
(c) I > Ill > II
33. Consider the following reaction sequence.
(b) II > Ill > I
(ti) I > II > Ill
(o) 1-Phenylpropenc
(b) 1-Phenylprnpanol
(c) 3-Phcnylpropcnc
(a)©(NO, (b) 2

(c)
times
LS limes
CIIJC • CH /:._ A ~ B. (ti) 2-Phcnylpropan-2-ol. (d) 4 times
38. Major producl of the reaction given below is

dr'·•:01
The products (A) and {B) respectively. arc : 2. In Ssl reaction of an alkyl halide on chiral centn.-s. there is:
1a1 rn,rn,rnc1, and c11,c11,rno (b)~ (a) 100 o/• racemi7.ation
(b) CHJCCl1CH.l and CH.lCOCH.l
(c) Cl-llCCl1C I-IJ and CIIJC • CH NO: (b) Inversion more than relention leading to partial
(d) CHFHCICHFI and CI-IJCH(OH)Cl-lpl-l mcemi7.ation

~
(c) 100 o/• retention
(u)~(h)~
.J4, ';:'.:\~~ r(Majo,eliminaiion produCI) (d} 100 o/• inverston

The product r is

(a)~
(c)d- Id)~

39. Which one of !he following substrate will be the most

3. Ethylene glycol on reaction with PCl5 gives:
(a) Ethylene dichloride
(b) Ethyl chloride

(c) I , 1-Dichlorocthane
reactive for E1 reaction?

I<)~ "' 43. Which reagent can be used in lhe Friedel - Cran acyla1ion
(d) o,manc

rr
(a) ~ 1 1,--CII, 4. How many dichlorocyclohexane would be produeL-d upon
reaction?
free radical chlorina1ion of chlorocyclohcxane?
35. (X) •k.!Olt (major producl) la) Cll1COOCOCII, lh> rn,coc1 (al 4 lhl 6
(c) CI-IJCH2COC1 (d) All of these
~ Mc I<) 8 (ti) 9
The reactant (X) is: (h) P"-711-CH, -CH, 44. Nitration of chlorobent.l'fle lakes place 1111
5. Which of the following is Ss2Ar reaction?
(a) o - Pos11ion (b) m - Position
Br
lu)O::r (c) Br - CH • CH - CH~- CHJ ( c) p - Posi1ion (d) Both o- and p - posi1ions ~Br
-.,.M, r, 45. The antiseptic action ofCl·IIJ is due to l8J +i-T

,,,&_, (d) Cll:-C:H--f-C:11,

Cll 1

HALOARENES AND POLY HALOGENATED

(a) lodoform itself
(b) Liberation of free iodine
(c) Pat11ally due to iodine and partially due to CI-IIJ itself
(ti) None of the above
LNo..i:r
l9
Br ~r
COMPOUNDS 46. CCI_. is a well known fire extinguisher. l·lowcvcr, af\er using
ii to extinguish fire, lhe room should be well ventilalt.-d.
II
J6. ~ tH- Cfl, Ale. KOH NaNH1 This is bt.-causc
X----Y
40, Fullnamcof Cl - @ - { @ -ciis: (a) II is innammablc at highl'f tcmpc..-raturc.
CH,CH,Br
CCI, (b) It is toxic.
X and Y arc rcsJX-ctively
( c ) II produces phosgcne by reaction with waler vapours al
(a) I, I , l-lrichloro-2, 2-bis (p-chlorophcnyl) ethane
lu) ~ C = C - Br ~ C = C - C,11, high tt.-mpcrature.
(b) I. l-dichloro-2. 2-diphcnyl trimcthylc1hane
(d) II IS COITOSIVC.
(c) I . l-dichloro-2. 2-diphcnyl trichlorot.1hanc
47. Aryl halides arc less reactive 1owards nucleophihc
(d) None of these
lb) (§rC =CII (§rCll,- CH,- C=CII substttution rcaclions as compan.-d to alkyl halides due lo:
It/) ~ r + O H - > @ "Oll +ll~
4 1. When phenyl magm.-sium bromide reacts wi1h t-butanol, the (a) The formation of less stable carbanion
product formed will be (b) Longer carbon halogt.-n bond
(a) Benzene (b) Phenol ( C') Inductive cfft.-ct
l<I ©"CH=CH, . ©"CH,- CH,
(c ) t-butyl benzene (d) t-bulyl phenyl ether (d) sp 2- hybridi7_cd carbon attacht.-d lo the halogen

6. Following arc the curves for nucleophilic substitulion 9. The oxida1ion ofCHCIJ by air & light is preventl-d by adding 14. Which n:oclanl reacts fas1cr wilh Nal in DMSO? 19. Arrange 1hc following compounds in the order of decreasing
reaction: (a) CHJCOOII rate of hydrolysis for Ss I reaction.

(l)f~
ITS. I (b)
(c )
Ci11 50 H
C HJCHO
(d) CH1COOCll1
(a) ~ ~' (b) 6CI (I) @-<:H,-Br

lc)6 H,c-@-cH,- Br
10. For the reaction CHJ CH(X) CH1 CI-IJ
l Product ( II )
Rcac1ion coordina1c
rr.s.1
•~• CH 3 - CH• CH - CHJ+ CH2 • CH - CH1 - CHJ
It•) C HJ- Cl·I • CH - CHJ predominates. (d)c5CI
lll)f~ (b) C !-1 2 • Cl-I - CH1 - Cl-11 pn.-dominatl"S.
(c )Both arc formed m equal amounts.
(Ill ) CH,-CH,- @ - c H ,- Br

(a) o
(d) The prodoct ratio depends upon the type ofX. 15. Rate ofSs2 will be negligible m
(IV)
CH,,,_CH- @ - cH!- Br
11. In the given pairs, which pair has the fi rs1 compound more
J! Reactant
reactive than second foe Ss I reaction? Cit(

I\ @-rn,ci (a) II > Ill > JV > I (b) IV > Ill > II > l

1au
g•II IT.S. (u)@-cl ( c) Ill > IV > JI > I (d) I > II > Ill > I
20. Which of the foUowmg reaction 1s not expected to give a

(<)6
(Ill)
:;i

j
c..
Reactmnt
Product
(bl~I
-ty Cl
sa!lsfactory yield of alkyl iodide'!
(a) CIIJCll20 II + Kl + IIJPO_.-.
(b) CHJCH!OI-I + PIJ ~
(a) 'I' is potential energy diagrnm for Ss2 reaclion lhnt takes
place with a negative potential energy change. Mc (c) CHJCH2Br + Nal ~
l cl ~ C l ~CI
(bl ' JI ' is po1en1ial crh.'fgy diagram for Ss2 n:ac1K)n with a I ••
16. Mc-C-CH,-011 ~ Map producl (d) CH,Cll 2C00Ag + 11 ~
positive potential energy change I .
(c ) ' Ill ' shows potential energy diagram for Ss I reaction Mc 21. Treatmenl of ammonia with excess ethyl chloride will give
wi1h large cncrgy orac1iva1ion for firs1(slowcs1) sh:p r CI ± Cl Tht major produc.:t is: (a) D1cthylaminc
(d) All of the above (b) Ethane

7. An oplically active alkyl bromide X (Ce,H uBr) upon (dlu u (c) Mcthylaminc
(d) Tetracthyl ammonium chloride
treatment with cthnnolic KOi-i solution forms two alkenes
Y and Z with their mok-cular formula (Ce,11 1!). Y and Z 12. Which oflhc following compound can not give Ssl reaction 22. In the 1-lunsdicckcr rcocuon. the compound
arc positional isomers. Z upon treatment wilh cold, dilute

J:B,
easily? CHJ
alkaline KMnO"' solution gives a mcso-diol. Hence, Xis
(a) 2-bromohexane
(b) l-bromo-2,)-dimethyl butane
)<B, CHJJ -COOAg is heated with:

(c) 3-bromohcxane (a)(QJ (blu

17. The reaction of SOCI, on alkanols to form alkyl chlorides !i1,
(d) 2-bromo-2,3-dimethyl butane gives good yield btta~ (a) Cl-l1Br ( b) Br2 in CCI~
(a) Alkyl chlorides are imm1sc1blc with SOCI, . (c) CHJBr + Agf (d) Nal + AgBr

(c)6
8. An organic compound X (C,/lu Br) is optically active. X
on trea1menl with (CHJ)JCOK in (C Hl )JCOH gives Y (b) The 01her products of 1he rcacuon arc iasrous and 23. In Si,,:2 reaction. 1f we double the conccnuation of rcactan1
(C/'J Hn). a majorproducl. Yon treatment with Br2- CCI_. in escape from reaction m1x1ure.
(c) Alcohol and SOCl1 arc soluble m water.
and nuclrophilc both. the rate ofSs2 reaction increases by:
the presence of FeBrl gives a dibromide which on further
(a) 2 t imes ( b) 4 times
treatment with NaNH1 gives Ct>H10 which is still oplically (d) The rcactioo docs no1 occw via mlennahate formation
(c) 8 times (d) No change
active. Hence, X and Y respectively are 13. Arrange these compounds in the order of increasing Ss2 of an alkyl chloro sulphite.
Br 18. Which compound undcrgon hydrolysis by Ssl mechanism
reaction rate:
(al~and~ a l the fastest rate?

~~Ar~
24. H+ H ~ X
Br
(b) ~ and ~
C~H,
Br
l< l ~ and ~
Cl
(I)
Br
(II)
Cl
(Ill)
Br
(IV)
(a) ~
lSJJ !, The product (X ) is:
Br (a) Ill < I < II < IV (b) Ill < II < I <IV (a) S-2-Chlocobutane
(dl ,Y-- and~ (c ) IV < Ill <I < II (d) IU < IV < l < U
(d)
(b) R-2-Chlorobutanc
(c) Mix1wc ofR and S-2-Chlorobutanc
(<)~
(d) 1-Chlorobutane
'
~emlstry Haloallames Haloarenes
bi
23. MeO............... Br ~ (X)
(2)
{MOM br<:mkkJ
8. Which one of 1he following s1a1emen1 is wrong aboul S~ IMc-th(nymc-thylbronuck-)

'
reaclion? Product ( X ) or the reaction is
(J)
LOALKANES (a) The rate of reaction is independent of the concentralic (a) Me-O-CH,-CH,-CN (b) McO.......__,.,.cN Cl
EPARATION OF ALKYL HALIDE of nucleophile. CN (a) 1 > 2 > 3 (b) 2 > 3 > I
(b) Nuc leophile anacks the carbon fro m the side opposit (cl Br.......__,.,.CN (d) <CN (C') 2 > I > 3 (d) 3 > 2 > I
In reaction: C2 Hj 0H + H X ~ C1 HjX + H 20 .
to where the leaving group is attached. 29. In each or the following groups, which is the strongcst(besl)
The order of reactivity ofHX is (c) Reaction occurs only inone step andthe bond formatio
24. Which orthe following halides will be most reactive in SN2 nuclcophilc?
(a) HBr > HI > HCI (b) H I > HC I > HBr & bond breaking takes place simultaneously. reaction and SN I reaction, rcspeclively?
(II ( II
(d) The ra1e of reaction oc (substratelfnucleophile). IIF-0- }
(c) HCI > HBr > HI (d) HI > HBr > HCI I. Me~Br
(2) ,...,..........ff in c 1-1p1-1
What is the main product of the reactio n between 9. Identify X and Y in the following reaction sequence.
2-methyl propene with H Br?
(a) 1-bromobutane
c1 H, Br ~product~ clH, NH~ II.
Me~c
I' (3)

(II ) ( I )
1-1 3 c - s-

(a) X • KCN, Y • LiAIH, OH" }

l
(b) I -bromo-2-methyl propane Mc 121 11 2~ in DMF
(c) 2-bromobutane (b) X = KCN. Y = Hp· Il l. Mc (3) NH,
~ r
(c/) 2-bromo-2-methylpropane (c) X = CH,CI. Y = AICl, /HCI (•I (IJ. (IIJ (bl (11).(IJ
When propylene reacts with HBr in presence of peroxide. (Ill ) (I J

,i,,"
(d) X = CH,NH,. Y = HNO2 (cl (IJ. (1111 (d) (111).(1)
the product fonned is
25. Which or the follow ing compounds will give curdy

6
(a) n-Propyl alcohol (b) Propylene peroxide 10. The least reactive a lky l chloride towards substitutio
(c) n-Propyl bromide (d) I. 3-Dibromopropene reaction is:
pr\.-cipitale with J\gN01 solu1ion? (21 )l_o inDMSO

Best method for preparing alkyl chloride is (a) Methyl chloride (3) C t-110 -
(a) ROH + SOC:12 ----> (al (bl Cll2 • Cll - CI
(b) Allyl chloride
(a) I. J ; 11. J : Ill. 2 (bl 1.2 : 11.1 : 111.3
(b) ROH + PCl5 ----> (c) I, I : II, 2 : Ill, I (cl) I, 3: II, I : Ill, 3
(c) Ethyl chloride
(c) ROH + PC!,-->
(cl) ROH + HCI ~
, The general fonnu la for alkyl halides is
(d) Vinyl chloride

II. ln the following reaction, the most probable product will be: (c)o (d) 6
ELIMINATION REACTION (E/E21

JO. ( ) < 1 "'.:'" l'(Majorcliminationproducl)

(b)u
(a) C,H2,.,X (b) C,H,,.,X
The product r is
(c) C,H,.,x (cl) C,H,,X H + H, ~ 26. Pick out the strongest substratc(s) for a Ssl reaction.
Ju)cr
(c)u
Which of the following does not give white precipitate when C, 11, Br
H,C+ H
boiled with alcoholic silver nitrate?
(a) Allyl chloride
C 2H_, q ,~
'
• • c .11.~ B, /2v- 9
' "Y C,11,
(b) I-butyl chloride
OH I. II. Ill. I V.
(c/) u
(c) Chlorobenzene (al Only I (bl Only II
H~OH
JI. (XI 1he major elimination producl among the following
(cl) Benzyl chlor ide H + H, (c) Only Ill (d) Only IV
(a) (b) produclS is
H,C H H3C H 27. During S,...2 reaction, which statl-menl is essential or correct? B,

8STITUTION REACTION (SN 1 /SN2/SNI)

Following reaclion (CHJ)JCBr + Cll 50 H ~
C2Hs C2H, (a) (R)-configuration or reactant essentially gives (S)-
configura1ion or product. cu,-O-{-e11, "".;°'' IXI
(b) Reactant having d-configuration essentially gives II

~
(CH 1 ) 1COC1 Hs + HBr is an example of: produce having/. configuration or product.
(a) Elimination reaction
(b) Free radical substitution (c)
H,C
H H,
(cl) H:iH
H 1C H
(c) Backside attack takes place on substrate atom having
leaving group.
(d) All orthc above
X'
( a ) ~IIC-CII: y (bl
~ HC-C:111

(c) Nuclcophilic subs1itu1ion

OH Cll 1
(d) Elcclrophilic subs1itu1ion C~H., 28. Arrange lhc following three chlorides in decreasing order
Cit, ( YCll i
towards SNI reactivity.
(c) (c/)v
(I I - Cl
'

12. The order or reac1ivi1y or the following halidl-s towards II. Fmd the product or the following reaction: 32. Amange 1he following 1n d\.-crcasmgorck.-rorstab1lity orthc1r
transilion state during elimination by a strong ba.~: (d) (§J'C =CH • (§J'C = C - C,H,

~~
hydrolysis by aqul·ous KOl·I IS:
(a) Ci-1 2 - Cl·ICI < CH 3CH2Cl-l 2CI < Cl-I: - Cl·ICll1CI

<ht rn, - c 11c1< rn, - c 11rn,c1< c 11,c11,c 11,ci

(c) CH1 - CIIC1-1 1CI < CH1 • CI-ICI < CH 1Cl·l 2Cll1CI p 11
°'··~,CY"'
I U Ill
37. I-Phenyl-2-chloropropanc on treatment with alcoholic
causlic potash gives mainly
(u) 1-Phcnylpropcne
l•l~H (hi>"' (ul II > I > Ill (hi II > Ill > I
(c/) CH1Cl-l 2Cl·l2CI < Ct-1 2 - CI-ICI < C!-1 2 • CI-ICll 2CI (cl I > Ill > II (d) I > II > Ill (h) 1-Phenylpropanol
IJ. The reoc1ion: JJ. Consider the following reaclion 5eqUl-OCC. ( c ) 3-Phcnylpropcnc
C/!pNa + BrC/1_, ➔ C/l_,-0-c/ l, + NaUr is calh..-d- (c) 7
'""-v,011 (c/))=.._ Cll1C ■ CH /:!. I A - :::1 I B. ( d ) 2-Phenylpropan-2-ol.

(c,) Frankland rcuclioo JI. Major producl or1hc reaction given below is

dr·•:01
19. For which alkyl halide. SN2 m\.-chamsm is most favoured'! The produc~ (A) and ( D) respectively, arc:
(h) Wunz reaction (a) Cll 1C ll1CIICl2 and Cll1Cl l1CIIO
(a) Cll 3CI (b) Cll1Cll 2CI
(c ) Williamson's synthesis (h) Cl·IFCl2Cll1 and Cll 1COCIIJ
( C) (Cll,J, CIICI (cl) (C11, 1,c - c 1
(c/) Cannizzaro reaction
(c) Cl·IFCIF ll1 and Cl·IF ■ Cl·I
20. Whichorthc ro11owingn:a.1Ulis imst ravoun..-dby5i.:2n:a1.1.UI?

.
14. Wh111 is lhc final product or1he given reaction?
(cl) rn,c 11c 1rn,c1and ClliCJl(OHJCll,011
CH - C ■ Cl-I ~ CIIJ- Clll - l Product (u) CH 1 Br +Olr ➔ CH ,OH + Br·
3
(c,) Cl·l 2 • CII - Cl·12 - CHJ
Br OH ~
l8J ~• · .,,.,, . . (uJ~ lh J ~

(bJef.!.'£,ef•IBr
34. N.OEt P (MaJOr elimination product)
(bl CHJ - CH 2 - C ■ C - Cl1 2 - CHJ

CU ■ C - Cl·1 - Cll - C ll The producl P is

(cl 1 2 1
(d) Clll-C •C - CH!- Clll (cJ ~ Jd ) ~
15. In the given reaction IXIand IYI will be: (c ) CH1CH10 H-1!:....+CH: • CH1
(•I~ 39. Which one or the following substrate will be !he mosl
!-11 Ct-11
C11, - C11, - C11, - O - CII, ~ IX l + IYI (d) CH1
j -CH1+0H ➔CH 1J-e11,+Br
rcac1ive for E1 reaction?

(al Cll1-Cl·l 2 -C11p 11 & Clll-CI

Br
I
0 1-1
I le) ~
Jal ~:11,-e11,
"'
(h) CH,-Cl·l 2-Cl·l1-CJ & CHp H
(cl rn,-e11,-e11,-e1& Cll,O,
21. Which is the major product or the following reaction?
35. (X) ik.!OII 0 (major product)

(X
C■N I. N.011 tuca.,,J
(d) CHJ-CH2 -Cll 2O H & CIIJ-01-1 _11 _ . Produc1 l.._)l.._Mc
1 10 11
The reac111n1 (X) 1s: (bi ro-yH--CH, --CII,

l•ICX:' (b) CX:'

16. (R)-2-Bromobutane is allowed to react with aqueous KCN. Cl·l:-CI ._,
l<kntiry !he producl formed in !he gin-n reaction. Br
w (c) Br - Cl-l • CH - Ct-1 2- CHl

(X
C■N
,M, Mc
"'
,.,&_,
i"I 11....r_,CN (al l h J ( IXc bH I

6
( d ) Cll:-Cl l-y-C:11,
~ 11 CH,--Ofl
"'- Cll,--CI Clli

(bl N
C+! CH1

C1 H 1 Jc) ( X
I
~b H tdJ
1 0'(:(C•N
I
(cl)

, M, HALOARENES AND POLY HALOGENATED

COMPOUNDS
~ Cll, 011 Br Br
(c) Equimolar amounts or(a) and (b) :::::::.... Cll1--0H J6 ' CH,
r;:::;ycH- ' Ale. KOH X~y
H
(d) Slight excess or (b)
17. Which or the following reaction is most expected to take
22. Which or the rcagl-nls shown below would accomplish !he -~ CH 1C H~ r
40. Fullnnmcorc1 - @ -{ @ c 1 i s :
fol lowing transformations? CCI,
place by Ss2 mcchunism? X and Y are resp..-ctivcly
(a) I, I, l-trichloro-2, 2-biJ (p-chlorophenyl) ethane
(a) ( § ( C = C- Br ( § ( C = C- C,H, (bJ I, l-dichloro-2, 2-diphenyl trimcthylethanc
(a) CH,--Cl l,~~B, + AgOH~ (c) I. l-dichloro-2. 2-diphenyl trichloroethane
(AJ (BJ
Ct-11 (r\TC= CII (d) None or these
(a) NaOI I 8111 - Tiff: H20;NaOl·I ( r \ TCH.-CH.-C=: CH
(h) (CH, ),C- Br+ KOH -1!.i.!!....+ (b) H 10- 8 1-11 - THF: H10;NaOl·I (h) ~ . ~ .. 41. When phenyl magnesium bromide reac1s with 1-butanol, the
produc1 formed will be
(c) CHJCH:CHBrCHJ + CHJCO: N• ~ (c) HBr in ether l·lg(OJ\c)/ 1-120 2; NaBII~ ~ CH,- CH , (a ) Bcn;r.cnc (b) Phenol
(d) (CH,l: CHBr + KCN .,..._,..,.. 1
(cl) NaNH/ 6 l-lg(OJ\cJ/ Hp 2; NaBI-I~ (cl (§J'CH= CH,
-~ (c) 1-butyl benzene (d) I-butyl phenyl ether