Eliminatio#' ffiilI'ffiHii

1. Which of the following alinl halide gives only one product (excluding stereoisomer) when
undergo E2 reaction ?

(E z : elimination bi-molecular)

CI

(d)

+
CI

2. zAt.,.A-.
I E, reaction
,
,.Hoifmann product)
+ ./v\
(Saytzeff product)

(A)In the above reaction, maximum Saytzeff product will obtained when :
(a) X=-I (b) X=-Cl (c) X = -Br (d) x=-F
(B) In the above reaction Hoffmann product is major when X is :
(a)' -I (b) - Ct (c) -Br (d) -F
B. 6l-H(P)
\-,/
when (P) undergoes Hoffmann exhaustive merhvlation (rwice) then the product obtained
r,r'ill be :

c^l fi'o) ror (*) (c)l- (d)l^

o-
I ?'
4, I
\Apr,
I
--Ei--+(A),
Ei e8o/o aY\\re
r -E-(B),
Er
on s5o:
(syn) X

o.-.,,o.-,^
(P) (Q)

Product (A) & (B) of the above reaction is :

(a)A=P,B=P G)a=Q,B=Q (c)A=P,B=Q (d)a=Q,B=P

ACH' HO-
Major product of the reaction is :
..4
'rt//
OTs

,"rry (b)u nry (d)eI-

Which of these dehydrates most easily ?

(a) CHs
-CHz -CHz -OH orC/'[i,
cHs

r.rloH (d) cH3

I

-! -.nz -oH
cHs

NaOCH"
Product; Product of the reaction is :
cH.oH
--+
(82 reaction)

(d) No reaction
ocH3
 NMe:
- Ho-
8.
- I l+A A
\-/ (Major)

Major product A is :

,rrd ,rr0 ,.rd ,.r$

H2SO4
9. + A
A
(Major)
Major product A is

G)aY),r@ (d)re
:

(,)OO
10. In which of the following reaction Saytzeff alkene is major product ?

!n'.
(a) cH: -cHz-[*ir., + O) cH3 -cHz -cHz *r, --Ef----+
f
(c) cHs -cHz
f',?' a
J
{ -cH3 r-BgoK
> r
(d) cH3 -cHz -cHz-Q cH3oK
' "fr,-cHg" a
>

f,
CH"
r'
Ph-+- H atc. KoH
+
11.
ph-1- I gr (E, reaction)
Major product of the reaction is :

cHa
Ph
-.
Ph ,/Ph
(a) t : ,ZCHI
C_. (b) : C-.
_c
- -cHg -C
cf,, -cHs
Ph
tn'a. Ph_CH_CH_Ph
,/Ph
(c) c-cH, (d)ll
Phtc: cHs oH
12. The conversion of 2, 3-dibromobutane to 2-butene with Zn is :
(a) Redox reaction (b) cr-Elimination
(c) B-Elimination (d) Both cr-elimination and redox reaction
13. 1, 3-Dibromopropane is heated with zinc dust in ether. The product formed is :
(a) propene (b) propane
(c) cyclopropane (d) 3-bromopropane
o

14. Reaction (1) alc' KoH , (A) (major)

ry"
?
Reaction (2) alc' KoH , (B) (major)
Qr.
o

Reaction (3) arc' KoH , (c) (major)

+Br
Product obtained in above reactions (1), (2) & (3) is :

(a) A - B but C is different

(b) A = C, but B is different
(c) B : C, but A is different
(d) A : B : C all product are identical

CI

15. Reaction (1) Cl

3 mole alc. KOH
(A)

CI

C1

CI

3 mole alc. KOH

Reaction (2) CI
(B)

C1 -.\\Cl
,rrttCl 3 mole alc. KOH
Reaction (3) C1

Product obtained in above reactions (1), (2) & (3) is :

(a) A =B,C isdifferent (b) A : C,B is different

(c) B = C,A is different (d)a:B:Cissame
#ffi qi*ffih r#r#ffi
L6. (x)
x is number of E2 product obtained
Br (including stereoisomers)

Find (x).

(a) 3 (b) + (c) s (d) 6

cHs
I

17. cHe
-9-tt cH-cH3 -ff!+(a)
CH3 Br
Major product (A) is :

@xz o) >< rctX. (d)><

L8. Which one of the following compound will be least susceptible to elimination of hydrogen
bromide ?
(a) Br CHz CHz NOz (b) gr CHz CHz CH:
- -
(c) Br CHz CH2 CN - (d) gr - CHz - CHz - COrEt
19. - - - andy(9o/o yield) are formed
Two alkenes, X(91% yield) - when - thJfoilowirg.o*pound
- is
heated.
cHs
@
N(CH3)3OH 9lo/o 9o/o

The structures of X and Y, respectively are :

(")O-cH3and *,ftcH3and
O-.n, ry.r,
(.)*cH2and (d)ftcH3and
20,
ry.",
In the dehydrohalogenation of 2-bromobutane; which conformation leads to the formation
OF.n,
of cr-2-butene ?

?', cHs

,,,]ff',0,)k." (c,H (d)

cHs

H
HH cHg

o-H o
il
CHs-C-Cl(2mole)
27. Pyridine
(a) (Ei)
o+ 1r1 + cH3co2H

o-H
 Product (B) of given reaction is:

"ro o)o .,0 .,,0

22. What product will be formed from Hoffrnann exhaustive methylation of following compound?
(i) CHs-l (excess)
Me2CHCH2NHCH2CHzMe
Ur*;--+Product
(iii)
A

(a) Me-CH:CHz (b) H2C : CHz

(c) CHs
"l- C :CHz (d) CH3 CH CH : CHz
- I
-
cHs Me
cH2- oH

2s. a t{--

-ital
3

Product (A) is:

(")a *,o ,.rO (d)o

CHo
Y"
24.
>.
O
OH
-F1products obtained are :

(a) Racemic (b) Diastereomers (c) G.I (d) Positional isomers

*',91,t
zs. $= (Ezreaction) . , ; Major product of the reaction is :

V"rc,
=
,4t.

+
(a) (b) (c) (d)

Q Q {
 r product of the reaction is :

,.r# (d)

27. The E2 product of the following reaction will be ?

Q
cHs
NaOH

(b)

(c) cHs
,,
G)m*u
28. An halide CsHrrBr on treatment with alc. KOH give 2-pentene only. The halide will be :

(a) CHs -CHz -CHz -CHz -CH, - Br (b) cHg -cHz -cHz -cH-cH3
-l
CHs Br
I

-l
(c) CH3 -CHz -CH-CH2 -CH3 (d) cH3 -cH -g -cHs
I

Br Br
29. End product (D) in the given sequence is:
cH3I
(2morarequivarenor(c) As2olH2o>(D)
r,Gr.
\,/ r;#ffi*;1(A)--Ee566y + (cH3 )3 N

(a) o

*ro ,r+ ,.r#

+ o OH
gO. For each of the following pairs of E 2reaction, select the one that occurs with the greater rate
constant.
cHs cHs I

I I

(1) CH3CH2CH2CI+CH3 - C- O- (2) CH3CH2CH2I+CH, - C- O-

cHs cHe

(3) H3C -CH -CHs +CHrO- (4) HsC -CH-CH3 + CH3S-

I I

Br Br

(')On.a + -oH' (6) + -oH

(a) 2,4,6 (b) 1, 3, 5

(c) 2,3,5 (d) 2, 4, 5
Br Br
I l- xNaNH2 y cH3l
31. CH3-C CH3--{:C-C:C-CH,
It
Br
-C -CHs
Br
-
x and y mole consumed.
Valueofx+y:
(a) s (b) 6 (c) 7 (d) B
3.2. The following bimolecular elimination reaction (Ez) is carried out with different halogen
leaving groups. The per cent yield of the two products (2-hexene and 1-hexene) for each
leaving group is listed below.
X
.L--. -/ + CH3O-
Leaving group Conj. Acid pK, %-yield of 2-hexene %-yield of 1-hexene
X:I -10 Blo/o 19o/o

X:Br -9 72o/o 2$o/o

X: CI -7 67o/o 330/o

X=F 3.2 3Oo/o 7Oo/o

\rVhich of the following statement is (are) true concerning this series of E 2 reactions ?

(a) Based on the pKu'S of the conjugate acid, I- is the best leaving group and F- is the
poorest leaving Sroup
(b) When I-, Br- and Cl- are used as leaving groups, Zaitsev's rule is followed
(c) F- is the strongest base (and therefore the poorest leaving group) and the transition
state for reactionwith fluoride as the leaving group has the least double bond character
(d) a, b, c are true
 , (1)q4
)J ^N(Ctrl";,
6ntro
LL,
A
(3)
33.

D
[;] fd B

Product (A) & (B) respectively are :

,.,4r: &
ar: ",5a, ar:
,.,5( ari & ,.,4f: ar:
34. 611 conc Hzso+,
,^, [li#*' , rrl 1ffi] (3) A
rcl

Product in above reaction is :

,rrO *,o (c) ,o,o

35. Major product obtained in the reaction of 1-phenyl-2-bromobutane with NaOMe is :

(a) (E)-1-phenylbut-1-ene (b) (E)-1-phenylbut-2-ene

(c) 1-phenyl-2-ethoxybutane (d) (Z)-1-phenylbut-2-ene

36. Which of the following alkyl halides give most complex mixture of alkene in anE, reaction ?

(a) CHg -CHz -CHz -CH2 -Br (b) cHs -cHz -cHz -cH-cH3
Br
cHs
I

(c) CHs -cH, -cH-cHz -cHs (d) CHS _C _CH2 _CH3

'l
Br I

Br

,rrr|34li,
37. ml] arc' KoH , (A)
[H (major)
\./
P{oduct (A) is :
 (")fFl o) ,ors'
Yo,
Bs'
ry"'+*(A); O {--co
Sum of number of cr-hydrogen present is compound A + B is :
(a) 18 (b) 1e (c) 20 (d) 21

g9. q4; (1) excess cHsr/xrco,

,,r.,
7\u)ff[l],"ilr'3t'3l/K2co3 H2C = CH-fH -CH = CHz
(2)Ag2o/H2o
(3) cHs
^
Identify A :

,",ff
\*/
G)

H
Br

cHs-cHz-c-cHz-r,
I
alc'KoH
40. , (A)
(major)
|
CH2(n - pr)
n-Pr=n-propyl
Product (A) is :

Me Et Me Et Me Et Me
(a)? ,o)l (c)v (d)?
Et

X
I

PTT HPr Pr Pr

Ph
I

41. (\on , Major product obtained by dehydration of given alcohol is

\,,,4.. "ioo :
 Ph

,.rd
xv NaOCHq (2mole)
41 Haoo
42. cH3oH
> 181

oH
Product (B) of above reaction is :

?' i'
,^,e(oo"*,,,d ,.,docH3,o,do,
43. Ph
- !H- cHz - fr, -4p Product
Br Br
Product of the above reaction is :

(a) Ph-CH:CH-CHz-Br (b) pr'{

(c) PH CHBr CH : CHz (d) Ph-C:C-CH3
- -

44.
ffo,
V -."" 'r* ,,o,
I
OH

G)l'il ,.,6
Product (A) is :

(.,+
H

NaOEt
45. -_--------,
PhA
NMe3
@

Major product of the above reaction is :

 Ph .\. Ph\6:
(a) t-./Ph G)
ph/ -
,-'n
-\
Ph/c: on M"

M.\ .zM'
\ph
(d) t-or,
Me Ph/c:

46.M ---
LDA
> A* Nz + ph-CH:CHz,productAis:

N
\NH-cHz-cHz-Ph

M
LDA : Lithium di-isopropyl amide

M
(a) (b)

,.rM (d)

\_*_l
47.
or
Major product of the reaction, when the given compound undergoes Hoffmann exhaustive
methylation is :

\
(a) .,ro ,ro (d) H2C : CHz

cHs

48. -+=P -- Major

Pyridine r product of the reaction is :

(a)
arre
 ,ro
Ph
lt
Ph

C: CH-C-OH

'*A , Product

Stereochemistry of the product is :

(a) Meso compound (b) Racemic mixture

(c) Diastereomer (d) Optically pure enantiomers

Which of the following reactant is used to obtain above compound (A). (Assume that EtO- is
used in all the reaction)
Br CH 3
H
=-./,
tBr
(a) oo) o (c) o (d)

H
sr.. (Cq\ arc. KoH
,(A), productA is:

HH
OH

(a) c)o" (c)

52. Rank the following in order of decreasing rate in an E2 reaction:

cHs

-'"'
ar'cH3
nr
\-'J<
Y,,,,,cHs
(a) (b) (c)
(a) a>b>c (b) c>a >b (c) c>b>a (d)b>a>c
sB. Pha I
KoH
EtOH,A
> (A) , Product (A) is
(major)
F

@tpnN G)pnA/ (c) ph/Y @)PIra

OEt OH

s4. a -S(A)Major
Br

INMegiS A
(B)Major
@
Relation between (A) and (B) is :

(a) G.I. (b) Positional isomer

(c) Enantiomer (d) Chain isomer

3NaNH2
55. Product ; The Product is :
Iiq.NH3

(b) HC:C-(CHz)3ONa

(c) NaC:C-(CH2)3ONa (d) H-C:C-(CH2)3OH

56. Which best describes the product of the following reaction ?

CH"

,r4'for-(d%Product
(a) Absolute configuration has been inverted
(b) Absolute configuration has been retained
(c) Racemization (loss of absolute configuration) has occurred
(d) Loss of chirality has occurred (the product is achiral)
57. What is the major product of the following reaction ?

CH"-CH"-C-CH
rzl\a
?' /"' n* ,product
cHs CHg
lffi
cHs

4,r.. I

_ cHs
/cH - cH3 /cH
(a) cr (b) "t/C: Ct
n": cHs cHs tH,
cHs

n.\
I
cH3
,cH - cH, \ lcHs
(c) ttanran, (d) ca.r,
n/': cHscH/c:

58. What will be the major product of each of the two reaction shown below ?
heat
" 'l
1. CH?CH?CHCH3
I
+N(cH3)g-oH l-r CH*CH:CHCH3+CH3CH2CH:CHz
- 'l
2. CH?CH?CHCH3+ CHTCH2ONa
heat
, l"xY
Br
(a) 1-X,2-X (b) 1-Y,2-X (c) 1-X,2-Y (d) 1 -Y,2 -Y
NHCH2CH?

59. + cH3I (excess) -----) product; The product is :

(a) a primary amine (b) a tertiary amine

(c) a secondary amine (d) a quaternary ammonium salt
cH2-oH
60. n* ,ta1---luslrle513;
A

(A) on heating isomerizes to (B). What is the structure of (B) ?

,,,0 6
OH

H
I
.o, ,.r0 (d)
6
Ph-C-Ph
cHz-cH2-oH
61. '*A , (major)
(A) , major product (A) is :
 .,i:: : iii 't.,., ... la , . , :.:

i
nt,,t. i,

fi0;ffifiiifi#

cH2-cH3
(b)

cH-cH2 cH2-cH3
(c)

62. Which of the following carbocation will undergo rearrangement ?

L e
(c) CHg-QH-C = O (d) cH3-NH-CH-CH-CHs
I I

cHs cHs

63. In which of the following reaction resonance stabilized product will form ?

cH2-oH .A..-oH
(a) -- H*

^----'
(b)
t, -+-,
H* (d) All of these
(c)
-A*

64. In which of following reaction rearrangement take place with change in carbon skeleton ?

QHs
161
(a) cHc-c-t'H, (b) cH3 -cH2cH2@
"l
cHs

(c) CHg - qH - cH, - 8u, (d) cH3 -cH@ -cH:

I

cHs
 f,;,,',,,, .,.,,',,,, ' , :',,. '
. ,ffItc #ft,
Consider the following reaction :

,OH
Which response contains all the correct statement about this process ?
(1) Dehydration (2) Ezmechanism
(3) Carbon skeleton migration (4) Most stable aikene will form
(5) Single-step reaction
(a) 1,3 (b) 1, 2, 3 (c) I,2,5 (d) t ,3, 4

H Br
66' H oF{ --J1EL--> (x) ;+:1--+ (r') (Major); Product ()') is:

CH:
(a) cls-2-butene (b) trq.ns-2-butene
(c) 1-butene (d) Iso-butene
Br Br
ti
6'7. CHz-CH : (dust)
+(A)
-g11" --!'
CH

Above reaction is an erample of 1,4-elimination. Predict the product.

(a) CH3 --CH:C:CH: (b) CHs == C --- Cf{?
(c) CHr-CHz-C:CFI (d) H2C -C
: CI{ __ CH :- CHz

Ph
68. --!9nc'llzso+--+ Major product of the reaction is:
OH

,rr@
(d) None of these
AIJfYL ITATTT'g$
Ph CHs Ph Et
llllr
69. Ph-c-c-CHs+ph-C-c-e, H2so4
>

tl
OH OH OH
ll OH
(A) (B)

PhO Pho
(p)
til
Ph-C-C-CH3 (q)
ril
ptr- C-C-Et
I I

cHs Et

PhO Pho
lil
(r) Ph-C-C-CHs (s)
lil
Ph-c-c-Et
I I

Et cHs
When (A) and (B) reacts with H2SO4 products obtained are :

(a) p, g, r, S (b) p, q (c) p, q, r (d) p, q, s

70. Which of the following compound gives even number of Hoffmann's exhaustive methylation
and elimination?

,"rQ (b) (')eT) (d) ^N{

I

.A,-:il-.n"J1
Tr. \rt[L;. \-] arc'KoH
, X=Numberof chirarproducts
" (including stereoisomer).
A
9cHs
(a) 2 (b) 4 (c) 6 (d) 8
$1S Oft$ i,ryemf,#E : rf*. l*.IHfr

1.

.9:-
!.7.
qI,
g3i
tl:
f?.
57.
70. | (a,b) l7L.