IIT-JEE CHEMISTRY BYFIITJEE ORGANIC CHEMISTRY

Time: 15 minutes
DPP NO-2 strutures
1. Compare relative stability of following resonating
S.No.Resonanting structures Order of stability Reason

(1) H2C =CH-Cl H,C-CH =

CI
(a) (b)

(2)

(a) (6)

(3) CH-CH =NH H,C =CH-NH

(a (6)_
CH-O- CH, CH ö = CH2
(4)
(a) (6)
H-N=C=O H-N=c-ö+H-NC=8
(5)
(a) (b)
(6) Me
a (b)
H~® OH
(7)
(a) (b)

(8)

(a)
-A-A b) (c)

(9)
O

(a)_ 6)
Se
(10)
H

(a) (b)
Fo
ZE0-

z=

:ze
 ORGANIC CHEMISTRY

IITJEE CHEMISTRY
BY FIITJEE Time: 15 minutes

DPP NO-3
of following resonating strutures Order ofReason
1. Compare relative stability
S.No. Resonanting structures stability

H
(1) O 0=
(a) (b) (c)
(2) H,N-CH = NH, H,N CH-NH2
(a) ()

(3)

(a) b)

(4) Me-N -> Me- NO

(a) (6)
(5) H=N=N-H H-C=Ñ-N-H
(a) (6)
(6) HC HC = C = 0 Me- CH-C=o

(a) (6)

H-C N-H
(a) (6)

(8) CH-A, CH-C CH,

(a) (6)
(9) CH,-C Ç-CH, CH,= -CH,
H H

(a) (6)
(10)

a) (b)

6
 3

:O
1
1 O

O+
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IIT-JEE CHEMISTRY BYFIITJEE Time: 15 minutes

DPP N0- 6
compound
Given the relative Stability of the following
Q.1

H
(v)
iV)
(Gii)
Me
Me Me
Me-CH-CH
= CH- C- Me
CH-C Me
Ph-CH,- CH
=
-

2 Me
Me

(i)
(i)
Me Me
Me
Me--HC = CH-C-Me
PH CH CH-C-Me
Me Me
Me
(ii) (iv)
Me
Me-C-CH,

3
Me ÇH- H- CH, Me-CH CH
Me
Me (iv)
(0) (ii)

) (i) (Gii) (iv

' 5

) (i) () (iv)

i) (i) Gii) (iv)

HC C = CH2 Me-CH CH2

) i) i) (iv)

12
 UTJEE CHEMISTRY BY FIITJEE ORGANIC CHEMISTRY
Time: 15 minutes
DPP NO 7
Given the relative Stability of the following compound

(i) iv) (v) (vi) (vii)

(i)
O (ii) (iv)

CH CH, ÇH

CH, CD CT
) (i) (ii) (iv)

Me
CH çH ÇH
A

(i) (iv)

CH, CH, CH,

5.

) (ii) (iv)

CH, ÇH, CH CH

CF CCI Me
() (i) (ii) (iv)
 ORGANIC CHEMISTRY

IIT-JEE CHEMISTRY BY FIITJEE Time: 15 minutes

DPP NO-8
Q.1 Given the relative Stability of the following compound

1.

(i) (ii)

) i) (Gii) (v)

3 -CH°(Et),CH (Et)c -CH-CH

) (i) (ii) (v)

(i) (ii) (iv)

) Gi) (ii) (v)

6.

) Gi) (ii) CO (iv)

7.

() Gi) (ii)

14
 IT-JEE CHEMISTRY BY FIITJEE ORGANIC CHEMISTRY
DPP NO-9 Time: 15 minutees

Q.1 Given the relative Stability of the following compound

(i) (ii)

(i)

ii)

(i)
[o]
i) (ii)

5.

() (i) (Gii)
6 CH C = C- CHb HC CH-C= CH
) i)

-CEC- ~CEc-
H,C-C HC-C=C-CHa
(i) i) (ii) (iv)
CH, H,
8.

) (i)
15
 ORGANIC CHEMISTRY

IIT-JEE CHEMISTRY FITJEE Time: 15 minutes

DPP NO- 10
a.1 Given the relative Stability of the following compound

2.

CH, CH
3. A.
CH
CH ii)
(i) 0) 6i)

CH, ,CH,

CH, CH,
6.

) (i) () (Gi)

7. 8.

) )
H3O o HOo
CH, CH
9 10.

i) () i)
Q.2 Hyperconjugation involves
(A) Delocalization of s-electrons into an adjacent p-bond.
(B) Delocalization of n-electrons into an adjacent double bond.
(C) Delocalization of n-electrons into an-adjacent double bond.
(D) All are true

16
 IIT-JEE CHEMISTRY BY. FIITJEE ORGANIC CHEMISTRY
Time: 15 minutes
DPP NO- 11
Q.1 Hyperconjugation is posslble in
(C) carbocatlons (D) all of these
(A) alkenes (B) alkynes

Q.2 Hyperconjugation is posslble In (D) Amines

(A) Free radicals (B) Carbanlons (C) Alcohols

Q.3 Hyperconjugation occurs in

(B) CH C H - C H = CH2
(A) CH CH CHa
CH (D) all ot these
(C) CH CH
CHS
Q.4 Hyperconjugation occurs in

CH
(B) CH-CH CH-CH3
(A) CH,¢-CH CH,
CH
(C) Ph CH = CH2 (D) CH
Q.5 Hyperconjugation occurs in

CHCH CH

(A) (B) (C) (D) cH,

Br
CH CH
Q.6 Hyperconjugation ocurs in

(B)
(A)
CH
(D) all of these
(C)

Q.7 Hyperconjugation occurs in

cH -CH, (D) both (B) and (C)
(A) CH, (B) CH, -CH, (C)
CH
CH
Q.8
-CH
How many hyperconjugable H-atoms does this cation has?
(A) 10 (B) 6 (C) 12 (D) 15

17
 CH,
Q.9 CHN
-CH,
CH H-atoms does this cation
has?
(D) 8
How many hyperconjugable
(B) 6
(C) 12
(A) 5

Q.10 HA-¢-CH = CH

be written as
Canonical structures due to hyperconjugation in this molecules can
HAN H
H(A) H CH-H, C=CH-EH, -
C= CH-CH,
H L H B

Hax H
C=CH CH, -
H
(B) C= CH H, - CCH-H,
HHS HH HH
(C) both (A) and (B)
(D) none of these

CH CH

Q.11
cH
OlCH
CH
Amor these compounds, which of the following orders is correct for their nobond-resonance
energy?
(A)Ill> II>| (B)I>lll (C)I ll>II (D)Il>Il>
Q.12 Compound Homolytic bond
dissociation energy
CH,CH+H 104 Kcal/mol
,CH CH,
CH,-CH CH, +À 92 Kcal/mol
CH CH
Notice the hemolytic bond-dissociation energy of the alkanes. Now, ignoring the contribution of
inductive effect, no-bond-resonance energy of tert-butyl radical can be calculated to be
(A) 6 Kcal/mol (B) 10 Kcallmol (C) 12 Kcal/mol (D) 14 Kcal/mol

Q.13

Among these cycloalkenes, which of the following orders of stability is correct?

(A) I> l> lll (B) IIl >I>I (C)II> I> Il (D)Il> IIl >|

18
 Q.14

Among these dienes, whlch ofthe folowing orders of stabilty is correct?

(A) I> Il > |l (B)I>Il>I (C)Il> IIl >I (D)II>1> II

CH,
Q.15 CH,
IV
Which of the following statements is correct, about thesecycloalkenes?
(A) Stability difference between I and Il is more than that between lll and IVV
(B) Stability difference botween I and Il is less than that between lIl and IV
(C) Overall, stability order is l> Il> | > IV
(D) None of these

Q.16
cH C CH
CH
CH,
H
CH H

H CH
Which of the following orders is correct for heat of combustion of these isomeric alkenes?
(A) I> I> II (B) IIl> l >| (C)IIl> > II (D)I>Ill>|

CH2 C H - C = C--CH = CH2

Q.17

Which of the following orders is correct for heat of combustion of these isomers?
(C)I= II (D) Not predictable
(A)I> II (B)I>T

Q.18

Which of the following order is correct for heat of combustion of these isomers?
(A)I>Il> (B) IIl >I > (C)Il> IIl>| (D)>I>| |

ÇH, CH
CH-CH,-CH,

Q.19
(o) O CH,
CH,CH CH
Which of the following orders is correct for heat of hydrogenation of these compounds?
(A)I> Il> III (C)Il+ (D)I> III> I1
(BTTI1>1
 Q.20

of these compounds
orders is correct for heat
of hydrogenation
Which of the following (D)II>lll>|
(A)I> II > II (B) Ill> II>I (C)1>1>|I

Q.21
-I.
Which of the following orders is correct for heat of hydrogenation of these compounds?
(A)I> I> |II (B)l > I>| (C)II>I> II (D)I> III> |I

Q.22

Which of the following orders is correct for heat of hydrogenation of these compounds?
(C)Il>I> II (D) l > I> II
(A) I> I > lII (B)Il>I1>|
CH
Q.23 CH-CH, =cH,

Which of the following ordérs is correct for-heat of hydrogenation of these compounds?

(A)I> I1 > Ill
(B)Il>Il>I (C)Il> 1> Il (D)II>> lII

CH CH CH
Q.24
CH, CH CH
Which of the following order is correct for heat of hydrogenation of these compoupds?
(A) I> Il> III (B) Il >II>I (C)Il> IIl >I (D)Il>>I
CH
Q.25
CH,
a and b are the length of these two C = C bonds. Now, which of the following orders is correct?
(A) a = b
(B)a <b (C) b > a (D) Not predictable

CH,
Q.26 al
CH,
a, b and c are the length of these C Cbonds. Now, which of the
=
following orders is correct?
(A)a =b= (B) a > b>c
(C)c>b>a (D) b > c>a
 Q.27 Inductive effect of
NO2 group operates in
-

NO, NO, NO
(A) (B) ( (D) all of these

Q.28 lductive effectof CH group operates in

CH, CH, CH,
(A) (B) C) (D) both (B) and (C)

Q.29-CH3 C - -0

Which of these groups has + I effect?

(A) I (B) II (C) II (D) all of these

Q.30

Hybridization of the negatively charged C-atom of this anion is

(A) sp (B) sp2 (C) sp (D) unhybridized
 ORGANIC CHEMISTRY

CHEMISTRY BY F I T J E E Time: 15
minutes
IIT-JEE

DPP NO- 12

Q.1
this carbocation
is (D) sp
Empty orbital of (C) sp2
(A) 2p (B) sp
resonance stabilized?
carbanions is not
the following
Q.2 Negalive charge of which
(C) (D)
(A) (B)

OCH,
QCH,
QCH,

Q.3
OCH,
OCH
òCH,
carbocations?
Which of the following orders is correct for the stability of these
(A)I> Il> Il (B)IIl> I1>| (C)I> II> Il (D)II>I>

Q.4 I

Which of the following orders is correct for the stability of these carbocations?

(A)I> Il> lIl (B) Il>1> (C)Il>>lII (D)I>I1>1

Q.5

Which of the following orders is correct for the stability of these carbocations?
(A)I> II> III (B) Ill> I1 > (C)Il>> II (D) Il> Il>

Q.6

Which of the following orders is correct for the stability of these carbocations?
(ALL2l (B) IIl>II >| (C)> IIl>|I (D)II>1> llI

22
Q.7

Which of the following orders is correct for the stability of these carbocations?
(A)I> II> (B)Ill> Il > (C)II>1> (D)Ill>>

Q.8

Which of the following orders is correct for the stability of these carbocations?
(A) I> l> ll (B) IlI> II >| (C)II> |> III (D)I>Il1>||

Q.9 Which of the following reactions is not possible?

A) -OH HClo, +H2O

Hclo +H2O
(B) -OH-

(C) both (A) and (B)

(D) none of these

Q.10 Which of the following reactions is not possible?

(A) - -CI- AgClO

HO
-OH

(B) -CI
AgCIO, -OH
HO
(C) both (A) and (B)
(D) none of these

23
 CH,--cCH,
CH,- H- CH
Q.11 CH,-CH,
CH
carbanlons 7
of these
corroct for the stablty (D)I> |I> II
Which of the following ordors ls
(B)Il> >| (C)II>>
(A)I> II > lI

Q.12 CH,-CH, CH, CH-CH,

Which of the following orders is correct for the stablity of these carbanions
(D)II>> IlI
(A)I> l1> I (B) Il >> 1 (C)Il> Il >|

Q.13 (O O
CH
Which of the following orders is correct for the stability of these carbanions?
(A)I> II > ||I
(B)Il>I1>> (C)Ill> >II (D)II> Il1 > |I

CI

Q.14
O
CI

Which of the following orders is correct for the stability of these carbanions?
(A)I>I> (B)l>I1>| (C)I>> I ( )Il>1> III

NO,
Q.15
NO,
NO
Which of the following orders is correct for the stability of these carbanions?
(A)I> I>Il (B)II>I> (C)Il> > |1 (D)Il> IIl >I

Q.16 CH CH- CH,

Which of the following orders is correct for the

(A)I> |I> II
stability of these carbanions?
(B)ll>I> (C)1> Il> (D)I>Il>

24
Q.17
CH,-CH=CHa
C4,-CH=0
CH,-CHa-CHa
Which of the following orders is correct for the stability of these carbanions?
A)>l>I (B)Il> II>| (C)Il>> (D)Il> IUl>1

Q.18

I
Which of the following orders is correct for the stability of these carbanions?
(A)I>ll> l (B) IlI> II>| (C)II> I>| (D) Il > | > III

O 0 O
Q.19
0 =0
Which of these carbanions is sp* hybridized?
(A)I (B)II (C)II (D) nonw of these

CH,
Q.20 CH CH-H, CH-CH, CH-
CH
Which of the following orders is correct for the stability of these radicals?
(A)I>Il> (B) III> II >| (C)I> II1> | (D)IIl>I>I

Q.21
CH
CH,
Which of the following orders is correct for the stability of these radicals?
(A)I>> B) II > || >>1 (C)Il> 1>III (D)I> Ill >I
Q.22 CH,-H
CH
CH,CH,H CH-H
H
Which of the following orders is correct for the
C-H bonds? energy required for homolytic cleavage of indicatec
(A) I> II> Ill (B) Il>I1>1 (C)IlI> >I (D)Il> IIl>|
Q.23
CH
CH
homolytic cleavage of indicated C
which of the following orders is correct for energy required for
H bonds?
(A) > Il> (B) Il> ll> (D) I >> I
(C)II>>I
Q.24 CI-CHa-COOH
Br-CHa-CoOH
-CH2-COOH
Which of thefollowing order is correct for the acldlc strength of these carboxylic acids
(A)I Il> (B) 1l > I1>I (C) Il>1> I (D) I> IIl >|

Q.25 Cl CH2-COOH

ON- CH2-COOH
CH3 C0OH
Which of the following order is correct for the acidic strength of these carboxylic acids?
(A)I> Il> lll (B) 1l>I1> (C)l>1>I (D) I1> Ill >

COOH
Q.26 COOH
coOH
H,C HCOOH
COOH
Which of the following order is correct for the acidic strength of these carboxylic acids?
(A)I> II> I (B) III>Il>| (C)Il>1>II (D) I1> ll >

CH,
Q.27 CH,-$i-CH,-COOH
CH
In this molecule, the effect of trimethylsilyl group (encircled) on the acidity of -COOH group is of
(A) strong electron donating nature (B) strong electron withdrawing nature
(C) weak electron withdrawing nature (D) both (A) and (C)

OH OH QH
Q.28
0
o

Which of the following order is correct for the acidic strength of these compounds?
(A) 1> II>|II (B) Ill >|1> (C)Il>> ll (D) IIl>|> |I

26
 1
OD OD

Q.29

4O1D
Whlch of theno- OH groupa Is most acldlo?
(A)1 (8) 2 (C) 3 (D) 4

ED3

Q.30

Which of the following orders ls correct for the acidity of these indicated
H-atoms?
(A)12 >3 (B)3>2>1 (C)2 1> 3 (D) 1 3 >2
 ORGANIC CHEMISTRY

IIT-JEE CHEMISTRY
BY FIlTJEE Time: 15 minutes

DPP NO- 13
Non-aromatlc
1. ldentify the Nature of compound
Antl-aromatic

S.No. Compound AromatlC

(1)

(2)

(3)

(4)

(5)

(6)

(7)

(8)

(9)

(10)

(11)

(12)

(13)

28
OCEOOO-dde
E I-Z
DO 00DO-O
O
o