Reaction Intermediate

IIT-JEE ChEmistry by N.J.
sir
ORGANIC ChemIstRy
S
.
J
.
REACTION
MECHANISM
r
i
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IIT-JEE ChEmistry by N.J. sir
ORGANIC chemistry
DPP NO-01
Time: 15 minutes
Q.1
(b)
CH3
_____
CH3CH2CH2
(o)
_ _ _ _ _ _ _
(c)
CHOH
2
_____
CH3 C C = O: _ _ _ _ _ _ _ _ _
:
(a)
(p)
_______ _
CH3
(d)
CH3CH2CH2CCH2
_ _ _ _ _
CH2
(q)
_________
(r)
_________
(s)
CH3
(e)
(f)
CH2
________
_________
S
.
J
.
`
(g)
PhCH2CH2
CH3
_ _ _ _
(h)
CH3CHCH2CH2
Ph Me
(i)
Ph
CH3O
CCH2CH2CH2
(l)
OH
(m)
CH3 Me
(n)
_ __ _ _ _ _ _
CH3CHCH2OH
(t)
_________
(u)
_______ _
(v)
_________
___
_ _ _
Ph
(k)
________
____
PhC CHCH2CH2
D
(j)
r
i
OH
(w)
_ _ _ _ _ _
_________
_ _ _ _ _ _ _ _ _
OH
(x)
________
CH3C Cet _ _ _ _ _ _ _ _ _
OH

ORGANIC chemistry
DPP NO-02
Time: 15 minutes
Dehydration of Alcohol
Conc.H2SO4 CH3CH=CH2 Q.11
Q.1
CH3CH2CH2OH
H / _ _ _ _ _ _ _
OH
170C
Mechanism:
(1)
Q.8
CH3 CH2 CH2 O

H
+ H+
CH 3 CH2 CH2
rds
CHCHCH
3
(2)
3, 3Dimethylbutan2ol loses a molecule of

water in the presence of concentrated sulphuric
acid to give tetramethylethylene as a major product.
Suggest a suitable mechanism.
Electrophilic addition:
CH3 CH2 CH2 +
CH3 CH CH3 + :O:
C=C
ENu
CC
E
CH3CH=CH2+ H3O+
Mechanism:
H
Energy profile diagram:
C=C
r
i
Nu
+ E C C
Reaction
Q.2
OH
OH
/ _ _ _ _ _ _ _
H / _ _ _ _ _ _ _
OH
Q.4
Q.5
OH
OH
H _ _ _ _ _ _ _
OH
Q.8
OH
(b)
C C
CH = CH2
CH = CH2
(iv)
CH = CH2
CN
(ii)
CH = CH2
O Me
NH2
(v)
(iv)
(iii)
COOH
(c)
(i)
(d)
H / _ _ _ _ _ _ _
(iii)
(i)
CH = CH2
Conc.H2SO4
_ _ _ _ _ _ _
OH
(ii)
NO2
H / _ _ _ _ _ _ _
Q.9
Q.10
Nu
E
Compare rate of electrophilic addition on alkenes:
(i)
Conc.H2SO4
_ _ _ _ _ _ _
Conc.H2SO4
_ _ _ _ _ _ _
OH
Q.6
Q.1
Nu
(a)
Q.3
Q.7
S
.
J
.
H / _ _ _ _ _ _ _
OH
H / _ _ _ _ _ _ _
Q.1
(ii)
Ph CH = CH2
(i)
(iii)
(iv)
(v)
PH CH = CH Ph
(ii)

HI
Q.1
CH2 = CH2 _ _ _ _ _ _ _ _ _ _
Q.2
KBr
CH2 = CH2
__________
HI
__________
KBr
Q.3
Q.15
HCl(2eq.)
CH3 C CH
__________
Q.16
HCl _ _ _ _ _ _ _ _ _ _
Q.17
dil.H2SO4
__________
H /H2O
__________
Q.18
Q.4
HI
__________
C = CH2
KBr
HI _ _ _ _ _ _ _ _ _ _
KF
Q.5
Q.19
H /ROH _ _ _ _ _ _ _ _ _ _
Q.20
H /H2O
__________
Me
HI _ _ _ _ _ _ _ _ _ _
Q.6
Q.21
S
.
J
.
CH = CH2
HCl
Q.7
__________
Q.8
HI _ _ _ _ _ _ _ _ _ _
D /D2O
__________
Q.22
H+
Q.23
HI _ _ _ _ _ _ _ _ _
(Ph)2 CHCHCH=CH2
Me
Q.10
Q.11
Q.12
HBr
C = CHPh
__________
Q.13
HCl _ _ _ _ _ _ _ _ _ _
CH2 = CH Cl
Q.14
HCl(2eq.)
CH CH
__________
H
__________
Q.25
HCl _ _ _ _ _ _ _
CH C CH2 CH = CH2
Q.26
CH C CH = CH2
Q.27
H
HOCH2CH2CH2CH = CH2
___
MeOH
HCl _ _ _ _ _ _ _ _ _ _
HBr
__________
HBr
__________
Q.24
Q.9
r
i
HCl _ _ _ _ _ _ _ _ _ _
HCl
__________
OH
Q.28
H /MeOH _ _ _ _ _ _
CH2= CHCHCH=CH2
H _ _ _ _ _ _ _ _ _ _
Q.29
O
H

ORGANIC chemistry
DPP NO-03
Time: 15 minutes
Q.1
O
CH3CHCHCH3
CH3CH2CCH3
Q.3
OH OH
H
H
OH OH
OH
Mechanism:
(1)
CH3 CHCHCH 3
+H
+
H2 O + CH 3CHCHCH 3
:
:OH OH
OH
:
OH
+
CHO
3
CH3 CH 3
S
.
J
.
NaNO2 + HCl HON=O + NaCl
(2)
H O N = O + H H2O +
(1)
N=O
+
N = O RN N = O RNN = OH
: :
RN= NOH
N2 R R N N : RN = N
+ O
NaNO2
R N N :
R N2
HCl
R NH2
Mechanism:
RN: +
Diazotization of primary amine:
H
Ph C CH 2
OH OH
(3)
Q.6
Q.7
Ph
OH
OH OH
H
Et C C Et
OH OH
Q.2
CC
OH
OH
r
i
OH OH
+
CH3 CH 2CCH 3 CH3 CH 2CCH 3
Q.1
CH 3
Q.4
Q.5
s
OH
CH3
RN = NO:

Demjanov Reaction:
OH NH2
OH
NaNO2
CH3 CHCHCH3
CH 3 CCH 2CH3
HCl
SbCl5
__________
Cl OH
OH
NH2
NaNO2
CH3 CHCHCH3 + N2
CH3 CHCHCH3
HCl
OH
O
H
OH
Br
AlBr3
Q.6
OH
NH2
NaNO2
__
OCH3
HCl
CH CH
NH2
Q.2
OH
NH 2
NaNO2
HCl
__________
Q.8
NaNO2
__________
HCl
Q.3
DPP NO-04
Non Classical Carbocation:
Q.4
Nu
ENu
C C
E
Mechanism:
C C
C=C
E
+ Nu
Nu
N
Nu
C C
Q.2
Q.3
aq.AgNO3
__________
2
CH2 = CH2
_______
Br2 _ _ _ _ _ _ _
CH2 = CH2
O
H
H
ORGANIC chemistry
Time: 15 minutes
Br2
_ _ _ _ _ _ _
CCl4
Q.5
ICl _ _ _ _ _ _ _
CH3 CH = CH2
Q.6
HOCl _ _ _ _ _ _ _
CH3 CH = CH2
Q.7
Cl2
_ _ _ _ _ _ _
CCl4
Q.8
Br2
_ _ _ _ _ _ _ _ _
CCl4
Q.9
Br2 /H2O
_______
Q.10
Br2
_______
H2O
Br
OH
S
.
J
.

C=C
OH
OH
r
i
AgI
__________
Q.7
I
Q.1
__________
+ CH3 CCH2CH3 CH3 CCH2CH3
Q.1
(1)
NaNO2
_______
HCl
CH3 CH CH
Q.5
Mechanism:
(1)
OH
Q.4
NH2
Q.11
Br2 /CCl4
_______
(1eq.)
Br2
_ _ _ _ _ _ _
CCl4

H
N
Q.12
Q.13
Diels Alder Reaction:
Br2 (CCl4 )
_______
(1eq.)
+ ||
HCl _ _ _ _ _ _
CH3 CH = CH2
COOH
Q.1
CH3Cl / AlCl3
COOH
COOH
CH3Cl
Q.2
H
Q.14
HO
CH3
______
HCl _ _ _ _ _ _
CH3
Q.13
The reaction of propene with HOCl proceeds via

the addition of
[IIT '2001]
Q.5
(A) H+ in first step
+
(B) Cl in first step
(C) OH in first step
Q.6
(D) Cl+ and OH in single step
B
OH
Q.18
Ans.
Q.23
Q.4
H 2O
NO
NO
(C) CH3 CH2 CH

Cl
Q.26
The number of stereoisomers

bromination of trans-2-butene is
(A) 1
(B) 2
(C) 3
A
Write down the structures of the stereoismers

formed when cis-2-butene is reacted with bromine.
[IIT '1995]
Ans.
H
Br
Me
Me
H
Br
Q.10
obtained by
[IIT '2007]
(D) 4
Q.5
Br + Br
H
H
(D) CH2 CH2 CH2

Cl
NO
Q.9
r
i
S
.
J
.
NO Cl
Ans.
Me
Br2
5 compounds of
(mixture)
Q.7
molecular formula C4H8Br2
[IIT '2003]
Number of compounds in X will be :
(A) 2
(B) 3
(C) 4
(D) 5
B
Q.8
CH3 CH = CH2 + NOCl P
[IIT '2006]
Identify the adduct.
(A) CH3 CH CH2
(B) CH3 CH CH2
H
Cl
Ans.
+
NO2
Q.15
Ans.
HOOC
Q.3
Q.11
Q.12
Me

ORGANIC chemistry
DPP NO- 05
Time: 15 minutes
Fill in the blanks:

O
Q.1
CH3
OH
OH
H
CH3
OH
OH
H
+ H+ H
Mechanism :
(i)
(ii)
O
H
Intermediatecarbocation
Rearrargemet
Intermediatecarbocation
Re arrangedcarbocation
O
(iii)
H +
Re arrangedcarbocation
(iv)
[H ] = - - - - - - - - - - - - - - t
(v)
Name of Reaction is - - - - - - - - - - - - - - - -
Q.2
OH
OH
S
.
J
.
CH3 O
CH3
Mechanism :
CH3 O
OH
OH
Product
CH3 +
r
i
H Intermediate Carbocation
Intermediate Carbocation rearrangedCarbocation
Q.3
(i)
(ii)
RearrangedCarbocation H+
Pr oduct
PH
NH2
OH
NaNO2 |HCl.
Pr oduct
NH2
PH
CH3
Mechanism :
(i)
C
H
OH
CH3
NaNO2 |HCl.
---- ---------
Rearrangement
H+ + - - - - - - - - - - - - - - - - - - - - - - None of Reaction - - - - - - - - - - - - - -

CH3
Q.4
CH3
CH3
C +
CH3
CH3
CH3
Q.6
Q.5 CH3 CH2 + CH3 CH2

(Major Pr oduct)
(Major Pr oduct)
Q.7
(explain)
Ph
CH 3
CH3
O
+
CH = CH 2 H / Ph
Mechanism :
(i)
Ph
CH 3
CH 3
+H
CH = CH2
(Intermediate1 )
(Rearrangement)
Nucleophile
Pr oduct
Intermediate3 (Intermediate2 )
HCl | CCl 4
Q.8
HBr
CCl4
PhCH= CH 2
HCl
ROOR/CCl 4
Ph
S
.
J
.
HBr
(ROOR)/CCl 4
CH3
Q.9
CH3
CH3
CH2
Br /h
aq.KOH
2
2
A
CH3
CH3
CH2
r
i
CH3
OH
Conc. H2SO4
HBr(ROOR)
C
B
CCl4
A & C are Idenitcal / Isomers / Positon Isomers.

Q.10
Ph
Ph
NaOH
OH
electrolysis
Ph
Anode
(I)
_ _ _ _ _ _ _ _ _ e +
Ph
Cathode
(i)
2H2O + 2e _ _ _ _ _ _
Ph
Ph
(ii)
Ph
(iii)
Intermediate - - - - - - - - - - -
Ph
CO2 +
Intermediate

ORGANIC chemistry
DPP NO- 06
1.
Time: 15 minutes
Which of following carbocation will undergo

rearrangement?
+
+
CH2
CH2
(a)
(b)
(c)
(f)
Ph C Ph
CH2 CH3
(g)
(A) , Major product (A) is

(major)
+
+
CH2 CH2 OH
3.
(d)
+
+
(e)
Ph CH Ph
(h)
(A)
O
r
i
Ph CH Ph
Ph
+
CH CH3
(i) CH2 O CH2 CH2 CH2

(B)
(j)
Ph CH Ph
+
CH2
(k)
(l)
S
.
J
.
(C)
CH3
(m)
Ph
Ph C OH
Ph
(n) CH2 CH2 CH2
(o)
+
CH
(q)
(r) CH3CH2CH2+
(t) (CH3)3 C CHCH3

CH2OH
2.
CH2 CH3
+
(p) CH2 C
=O
CH3 CH2 O
CH CH2
(D)
4.
OH
Reaction-1
(s) (CH3)2 CH CHCH3
(u) (CH3CH2)3CCH2+
H (A)
Reaction-2
OH
(A) an heating isomerizes to (B). What is the

structure of (B).
CH3
OH
Reaction-3
(A)
Sum of -hydrogen (A + B + C) is.
(B)
(C)
(D)
5.
OH
(A)
OH
(A)
(major)
(A)
(major)
(A)
(major)
H (x)

10
(B)
OH
OH
H (y)
H (B)
Reaction-2
OH
H (z)
(C)
OH
H (p)
(D)
Reaction-3
H (C)
OH
Total number of products obtained in above
reactions including minor products is (include
stereoisomer)
x y z p
6.
In which of following reaction rearrangement take

place with change is carbon skeleton.
CH3
+
(A) CH C CH
(B) CH3 CH2 CH2
3
2
H (D)
Reaction-4
Sum of -hydrogen is
8.
+
CH3 CH CH2 CH2
CH2OH
S
.
J
.
OH
(B)
CH3
(D) CH3 CH CH3
r
i
A+B+C+D=
In which of following reaction resonance stabilized

product will form.
(A)
CH3
(C)
OH
CH3
7.
Sum of -hydrogen in major product of the

reaction.
OH
Reaction-1
(C)
OH
(D) All
H (A)

11
ORGANIC chemistry
DPP NO- 07
Q.1
Time: 15 minutes
OH
Compare rate of dehydration (acid-catalyzed)
OH
OH
A+B
(h)
(i)
H
OH
H
CH3
(a)
A+B
CH3
OH
OH
A+B
(j)
OH
(b)
OH
OH
(c)
OH
(d)
OH
OH
H2 SO4
(m)
OH
CH3
(e)
S
.
J
.
OH
(n)
Q.2
Q.3
Predict the major product

dehydration of alcohols
(A) 2-pentanol
(B) 1-methyl cyclopentanol
(C) 2-methyl cyclohexanol
(D) 2, 2-dimethyl-1-propanol
of
(o)
(b)
H SO
CH2 OH
H PO
CH3
(f)
(r)
CH3
OH
(s)
Q.4
OH
H3PO4
Write Mechanism
(a)
OH
H2 SO4
(b)
CH3CH2CH C CH3
OH
(g)
Cl
H3PO4
3
4
CH CH2 CH3
OH
(e)
D
D
OH
CH3
D
H
D
2
4
CH3CH2C CHCH3
OH
(d)
(q)
CH3 CH3
OH
(p)
(c)
H2 SO4
CD3
OH
H2 SO4
OH
OH
acid-catalyzed
Identify-Product
(a)
KHSO4
170 C
H2 SO4
(l)
OH
OH
r
i
OH
(k)
OH
(c)
18
+ H2 O
H
OH
CH2 CH CH2 CH2 CH2

OH
18
OH
CH 3

12
Q.5
HCl
(a)
CH2
Me
Me
Predict Major Product

(i)
HCl
(b)
(j)
HCl
(c)
HCl
(d)
2-methyl propene
(e)
Hl
1-methyl cyclohexene
(k)
OH
OH
(l)
OH
OH
(n)
(o)
CD3
(b)
D
(q) D
OH
OH
(p)
(c)
S
.
J
.
(r)
(d)
OH
OH
OH
OH
r
i
(m)
Ans.1 (a)
(s)
Cl
Cl
(e)
Ans.5 (a)
(b)
(c)
(d)
Ans.2 (A)
Ans.3 (a)
(B)
(C)
(b)
(D)
CC=CC
(c)
(e)
(f)
(h)
(d)
N
(g)
Cl
Cl
I
(e)

13
ORGANIC chemistry
DPP NO- 08
Q.1
Time: 15 minutes
Identify major products:

CH3
HgSO4
(a)
CH3 C C CH H2 SO4
(d)
H
Ph
CH3
HgSO
2
(c)
CH3
(f)
Q.3
CH
(d)
C
HgSO4
H2 SO4
Ph
DCl (x)
D3O+
(y)
HgSO4
H2 SO4
CC
H3 O
HBr
CCl4
(e)
4
CH3 C CH
H SO
(b)
H
C=C
What will be major product obtained from

addition of HBr to each of the following
compounds.
(a)
CH3 CH2 CH = CH2
r
i
CH3
CH
H3 O
(e)
(f)
HgSO4
H2 SO4
(b)
CH2
(c)
CH3
CH3 C CH
CH
H3 O
(d)
(h)
H3 O
l-phenyl cyclohexene
(i)
H3 O
l-methyl cyclopetene
HBr
(j)
(e)
H2C = C
(f)
CH3 CH = CH CH3
(g)
HO
(h)
CH3 CH CH2 CH = CH2
Find total product in following reaction ? (including

stereoisomer)
(a)
OH
(x) products
N
Br2
HBr
CCl4
(y) (products) (Markonikoff products)
(i)
CCl4
OH
(c)
(j)
1.
(a)
(b)
H
HBr
(A)
(B)
CCl4
Br2
CH3
Ans.
OH
(b)
CH = CH2
(k)
(z) (products)
CCl4
CH2 CH3
CH3
HBr
Ph CH2 CH = CH2
CCl
(k)
Q.2
S
.
J
.
CH3
(g)
CH3 CH = C CH3
(c)
Me
(C)

14
O
3.
(d)
(a)
Br
(c)
CHD2
(g)
(e)
OH
Ph
OH
2.
M. I.
(a) x 3 ; y 2 ; z 5
(b)
A 1 ; B 1 ; C 2
(c) 3
(d) 2
(e) 4
(f) x 4 ; y 4
HO
M. I.
*
Br
Br
(h)
(j)
HO
Br
r
i
M. I. (i)
S
.
J
.
(k)
Br
(g)
Br
(k)
(f)
Br
(i)
Br
(j)
(d)
Br
(f)
(h)
Br
Br
(e)
M. I. (b)
Br
Me
M. I.
Br

15
ORGANIC chemistry
DPP NO- 09
Q.1
Time: 15 minutes
How will prepare following compound using alkene

as the starting material ?
OH
Ans.
1.
(a)
(b)
OH
Br
(c)
H3 O
(a)
(b)
H3 O
or
(d)
or
Br
CH3
(e)
Br
(f)
CH3 O C CH3
(c)
CH3
OCH3
Q.2
or
OH (i)
(g)
Identify reactant in following reaction

(a)
(b)
Br2
CCl4
Br
Br
2
(B)
CCl
4
Br
(d)
HBr
(C)
CCl
4
Br
HBr
(D)
CCl
4
CH3
(e)
HBr
(E)
CH 3 C CH2 Br
CCl
4
CH3
O
H O
(f)
3
(F)
(g)
(G)
racemic mixture of 2, 3
CCl
HBr
Write Mechanism
(a)
HBr
CCl4
or
(e)
MeOH
(f)
HBr
CCl4
(g)
(h)
dibromobutane.
Q.3
(d)
+ Mirror Image
Br
(c)
S
.
J
.
(A)
meso 2, 3 dibromobutane
2.
r
i
HBr
CCl4
or
or
or
H3 O
MeOH
(a) A Trans but-2-ene

(b) B cyclohexene
(c) C cyclohexene
(d) D 2-Methylpropene
(e) E can not prepared by alkene
(f) F Propyne
(g) G Cis but 2-ene
OH
H3 O
(b) PhCH2CH2OH Ph CH CH3

16
IIT-JEE Chemistry by N.J. sir
ORGANIC chemistry
DPP NO-10
Time: 15 minutes
OZONOLYSIS:
The reaction of alkene of alkene with ozone (O3) followed by hydrolysis is known as ozonolysis.
It is two types : (I)
Reductive ozonolysis In presence of reducing agent
(II)
Oxidative ozonolysis In presence of oxidizing agent
Reducing agents:
Zn, H2O or Zn, CH3COOH or (CH3)2S or (Ph)3 P etc.
Oxidising agents:
H2O2 or R C O O H or Ag2 O etc.
||
O
R
C=C
O3
step I
70C
R
R Zn/H2O
Reductive
C = O + R C H
C
H ozonolysis R
O
O
C
R
O
Oxidative H O
2
2
ozonolysis
Example 1:
R C R + R C OH
O
Mechanism:
C
R
S
.
J
.
R
O +
C=O
RCO
R C O
RCO
O+
r
i
[SCT-Cut the double bond

and paste two oxygen atoms
and vice versa]
R
O=C
R C R + R C H
Note : In case of oxidative ozonolysis aldehyde (not ketone) further undergoes oxidation which gives acid
as product.
Q.1
Give the product of the following reaction.

[ 7 2 = 14]
(i)
(i)O
3
H2C = CH2
(ii)Zn /H O
(vii)
H2C = CH CH2 CH = CH CH3
(i)O3
(ii)Zn /H2O
(i)O
3
CH3 CH = CH2
(ii)Zn /H O
2
CH3
(iii)
Q.2
Find out the structure of reactant.

[11 2 = 22]
(i)
(i)O
(i)O
3 CH CH
X
CH
3
2
(ii)Zn /H O
2
3
CH3 C = CH2
(ii)Zn /H O
2
(iv)
(ii)
(i)O3
(ii)Zn /H2O
(v)
(iii)
(i)O
(ii)Zn /H O
(vi)
O
X
(i)O3
(ii)Zn /H2O
(i)O
3
X
(ii)Zn /H O
2
O+
O+
(i)O3
(ii)Zn /H2O
(ii)

KJhalawar Road, Kota, Rajasthan (324005)
17
(iv)
(v)
(i)O
3
X
(ii)Zn /H O
(i)O
3
X
(ii)Zn /H O
How many species will be formed.

Q.4
(vi)
O /
Zn /H O
(iii)
(i)O3
X
(ii)Zn/H O
CH3
H 3C
C=O +
H
C=O
How many initial ozonoids are possible in given

reaction.
(i)
(i)O /
3
CH2 = CH2
(ii)Zn /H O
(vii)
(i)O
3
X
(ii)Zn /H O
(ii)
(iii)
(viii)
(i)O3
O
(ii)Zn /H2O
C10H12
+ HCHO
Q.9
(i)O
(ii)Zn /H O
C12H18
O
(x)
(i)O
(X)
(xi)
(i)O
+ HCHO
(ii)Zn/H O
2
C12H18
Q.3
Ans.
Q.21
3 C H O
C6H4
3 2 3
(ii)Zn /H O
Ans.
Give the ozonolysis product of the following.

H
O ()
3 3
(i) X
Zn
O
CH3 CH =
(ii)
N
O
3 ?
Zn /H O
How many species will be formed.
r
i
Only mole of the compound A (molecular formula

C8H12), incapable of showing stereoisomerism,
reacts with only one mole of H2 on hydrogenation
over Pd. A undergoes ozonolysis to give a
symmetrical diketone B(C8H12O2). What are the
structure of A and B?
O
(A)
(B)
O
If after complete ozonolysis of one mole of
monomer of natural polymer gives two moles of
CH3
CH2O and one mole of O = C CH = O. Identify
the monomer and draw the all-cis structure of
natural polymer.
[IIT '2005]
CH3
(a) CH2 = C CH = CH2
H
CH3
(b)
C = C
CH2)n
(CH2
OH
Q.22
(i)O /
3
CH2
(ii)Zn /H O
2
S
.
J
.
O + HCHO
O=C=O+
(ix)
(i)O /
3
CH3 CH = CH CH3
(ii)Zn /H O
H ,
(i ) O
(ii) Zn / Cl3COOH
Identify X and Y.
Ans.
O
, (Y) CH3 C (CH2)4 CH = O
(X)
CH3

18
ORGANIC chemistry
DPP NO-11
O
Time: 15 minutes
CHO
(C)
Q.1
(D)
CHO
CHO
is obtained by the ozonolysis of following?
Q.5
This compound on ozonolysis gives which of the

following compounds
O
(A)
(B)
(C)
(D)
r
i
O
(I) O
(II)
OHCCCCH2CCHO
O
Q.2
O3
?
O
ZnH2O H
O
S
.
J
.
Q.6
(B)
(C)
(D)
CH3
|
H
CH3 C CH3
|
OH
O3
(A)
(P) + HCHO
Zn,H O
2
Product (P) is
Q.7
O
||
(A) CH3 CH2 CHO (B) CH3 C CH3
(C) CH CH OH (D) CH3 CHO
3
|
CH3
Q.4
The reactants that lead to product (a) and (b) on

ozonolysis are
Q.8
(A)
(B) I, III, IV
(D) I, II, IV
Which of the following will give three different

compounds on ozonolysis
Me
(A)
(B)
(C)
(D)
Me
Which one of the following compounds gives

acetone (CH3)2C=O as one of the products of its
ozonolysis?
(A)
(B)
(C)
(D)
ozonolysis
Sentene
O
Which is the correct structure of Sentene.
HCHO
CHO
(a)
OHCCCCH2CH = O
(IV)
(A) I, II, III & IV

(C) I, II, III
O
O
(A)
Q.3
(III)
Which starting material should be used to produce

the compound shown below?
(A)
(B)
(C)
(D)
(b)
(B)
Q.9
In which of following reaction product formed is

aromatic

19
OH
Q.10
(A)
HBr
(B)
HF
KH
(C)
Propane reacts with chlorine in sunlight to give two

products. 1-chloropropane is obtained in 44% yield
and 2-chloropropane is obtained in 56% yield of the
total product. 2-Methylpropane reacts with chlorine
under same conditions to produce 1-chloro-2methylpropane 66% and 2-chloro-2-methylpropane
33% What will be the percent yield (X) of the major
product obtained when 1,3,5-trimethylclohexane is
treated with Cl2 in similar conditions. (Round
answer to nearest integer)
OH
H2SO4
(D)
HO
OH

DPP NO-12
Time: 15 minutes
Free Radicals:
Wurtz Reaction:
Na
S
.
J
.
Cl
Cl
Mechanism: (Free radical Mechanism)

(1)
Na Na+ + e
(3)
Na
________ _
ether
Q.8
R X
R R
ether
R X + e R + X
R + R R R
(2)
Q.12
(3)

R + R X R R + X
R X + 2e R+ X
Na
_______
ether
Br
Q.11
(2)
Cl
Q.9
Q.10
(Ionic Mechanism)
(1)
Na Na+ + e
Na
Q.1
CH3 Cl
_______
ether
Q.2
Et Cl
_______
ether
Q.3
CH3 Cl + Et Cl
_______
ether
Na
Cl
Na
Na
Na
THF
Na _ _ (Wurtz fitting)
Cl + Cl CH3
THF
Cl
Q.5
Q.6
Q.7
Br
Q.16
Cl
Ag/Powder
_______
HCCl
Cl
Q.17
_______
CH2CH=CHCH2
ether
Na
Br
Br
Na
_______
Br
ether
Cl
Br
Br
Na
_______
ether
Cl
Zn
_______
CH2CH2
Br
(Ph)3 CI
_______
ether
Na
_______
ether
Na
_ _____
Cl
ether
Ph Cl
_ _ _ _ _ _ _ (fitting Reaction)
Q.13
Q.15
Na
_______
Cl
ether
Cl
Q.14
Q.4
r
i
ORGANIC chemistry
Na
_______
ether
Q.18
Na
_______
ether
Br

20
ORGANIC chemistry
DPP NO-13
Q.1.
Q.2.
Q.3
Time: 15 minutes
On chlorination, an equimolar mixture of ethane and neopentane yields neopentyl chloride and ethyl chloride in
o
o
the ratio 2.3 : 1. How does the reactivity of 1 hydrogen in neopentane compare with the of a 1 hydrogen in
ethane?
Give product(s) in each of the following reactions
Br2 / hv
CH3 CH CH2 CH2 CH3
(A)
CH3
Bromination of methane is slowed down by addition of fairly large amount of HBr.
(a)
Suggest a possible explanation for this.
(b)
Account for the fact that addition of HCl does not have a similar effect upon chlorination of CH4.
r
i
Q.4.
Which of the following compounds on gentle heating, will undergo homolytic bond cleavage easily:
O
(A)
(B)
(CH3)3C OC(CH3)3
(CH3)2C O C CH3
(C)
(CH3)3C C6H5
(D)
(CH3)3C OOC(CH3)3
Q.5.
Amongst the following, the most basic compound is:

(A) C6H5NH2
(B) p-NO2C6H4NH2
(C) m-NO2C6H4NH2
Which of the following is most acidic?
Q.6
(A)
NH3
(B)
(C)
CH3 NH3
NH3
(D)
Write mechanism of following reactions?

(a)
Na
Cl
Et 2O
HC
(b)
Q.8.
S
.
J
.
NH2
Q.7.
(D) C6H5CH2NH2
Na
Ph3 CCl
Ph2 C
Et 2O
CH2
CH2
CPh2
Arrange the following in increasing order of stability.

(a)
(regarding stability of free radical)

CH3
(b)
CH2
Q.9.
CH2 , CH2
CH
CH
CH
CH2 ,
CH2
Supply the structure and type of intermediate species designated by
(a)
CH3 CH CH3 + H+ ? + H2O
(b)
CH3CH2 N N CH2CH3 ? + N2
|
OH
Q.10.
(c)
CH3CHI2 + Zn
? + ZnI2
(e)
CH3CH2Cl + AlCl3
AlCl4 + ?
(d)
CH3C CH + NaNH2
? N a + NH3
Name any organic compound which on electrolysis give H2 on both the electrodes.
Q.11. Given structure of major product formed by electrolysis of following salts.

(a)
(b)
COONa
COOK
COONa
COOK
(c)
COONa
COOK

21
CH3
Q.12
CH3
CH3
C +
C
(Major Pr oduct)
CH3
CH3
CH3
Q.13
CH3 CH2 + CH3 CH2

(Major Pr oduct)
Q.6
(explain)
O
+
Q.14
Ph
CH = CH 2
CH3
CH 3
H / Ph
Mechanism :
(ii)
Ph
CH 3
CH 3
S
.
J
.

(Intermediate1 )
CH = CH 2 + H
r
i
(Rearrangement)
Nucleophile
Pr oduct
Intermediate3 (Intermediate2 )
HCl | CCl4
HBr
CCl4
Q.15
A
PhCH2 = CH 2
HCl
ROOR/CCl4
CH3
Q.16
CH3
CH2
HBr
(ROOR)/CCl4
Br /h
CH3
aq.KOH
2
2
A
CH3
CH3
CH2
CH3
OH
Conc. H2SO4
HBr(ROOR)
C
B
CCl4
A & C are Idenitcal / Isomers / Positon Isomers.

22
Q.17
Ph
Ph
NaOH
OH
electrolysis
Ph
Anode
Cathode
Ph
_ _ _ _ _ _ _ _ _ e +
(I)
(ii)
Ph
Ph
Ph
2H2O + 2e _ _ _ _ _ _
(i)
Ph
CO2 +
Intermediate
Ph
(iii)
Intermediate - - - - - - - - - - -

DPP NO- 14
S
.
J
.
COOH
Kolbe Electrolysis:
O
NaOH
RR
electrolysis
CO2 + H 2
COOH
Cathode
Anode
Mechanism:
(1)
R C OH
+ OH
R C O
+ O
Q.6
Anode:
(2)
KOH
_______
electrolysis
R C O R C O + e
O
R C O R + CO2
R + R R R
Cathode:
(1)
2H2O + 2e 2O H + H2
Q.1
electrolysis
CH3 COOK
_______
Q.2
NaOH
Et COOH
_______
electrolysis _
COONa
_ _
NaOOC
Q.8
electrolysis
COONa __ _ _ _
NaOOC
Q.7
(2)
COOH
Q.5
HOOC
(1)
Time: 15 minutes
NaOH
_______
electrolysis
Q.4
R C OH
r
i
ORGANIC chemistry
electrolysis _ _ _ _ __ _
SO3 K
KO3S
COOH
Q.9
SO3H
NaOH
electrolysis
_______
COOH
Q.10
NaOH
electrolysis
_______
COOH
SO3K
electrolysis
_ _ _ _ _ _ _
Q.11
electrolysis
NaOH
_ _ _ _
COOH
Q.3
HOOC
electrolysis
SO3K
Q.12
KO3S
electrolysis
___
SO3K

23
ORGANIC chemistry
DPP NO- 15
Q.1
Time: 15 minutes
Matrix
Reactions
(A)
Number of dimerization product

(excluding stereoisomers)
Na
CH3 CH2 Cl
Dry ether
(P)
(Q)
(R)
(S)
None
Cl
Na
Dry ether
(B)
(C)
14
Na
H2C = CH CH2 Cl
Dry ether
Q.2
Cl
* 14
Na
+ CH3 Cl (H2 C CH2 )
(D)
Dry ether
Br
Identify major products.

CH2Br
(1)
+ 4 Na
AlHg
C2H5OH
(2)
Na
DE
14
(7)
I
I
I+
Cu
120260C
Cl
(4)
(6)
Br
(3)
S
.
J
.
Cl
Br
r
i
Na
DE
(5)
Br
(8)
Na
Dry ether
Na
Dry ether
(9)
Na
Dry ether
Cl
Na
DE
Br

24
ORGANIC chemistry
DPP NO- 16
Q.1
Time: 15 minutes
Cl
Identify the major product:CH2 I
(12)
Na
+
Dry ether
(1)
Na
Dry ether
CH3 CH2 Cl +
Br
Br
Br
(2)
Cl
(13)
Na
Dry ether
2.
Br
Br
CH2
CH2
(1)
rxn - coordinate
Br
Se (B)
Na
(A)
Dry ether
(4)
Br
Br
Br
Br
(2)
(3)
(4)
(6)
CH2 Br
(7)
Na
(A) + (B);
Dry ether
CH2 Br
3.
Na
H2C*=CHCH2Cl
A + B + C
Dry ether
Br
Na
Dry ether
(9)
Cl
(1)
(2)
(3)
(4)
Cl
Na
Dry ether
(10)
Cl
Na
Dry ether
(5)
(6)
rxn - coordinate
Cl + H CH3 H Cl + CH3
Bond energy
(A) & (B) are isomer.
(11)
CH3 + CH3 CH3 CH3
Na
Naphthacene
Dry ether
Br
(8)
hv 2Cl
Cl Cl
S
.
J
.
Na
Dry ether
(5)
r
i
Which of following is correct matching of energy

profile diagram?
CH3 Cl CH3 Cl
Na
Dry ether
(3)
Na
Dry ether
rxn - coordinate
E
rxn - coordinate
KJ
KJ
H Cl 432
CH H 440
mole 3
mole
When pentane is heated to a very high temperatue,

radical reactions take palce that produce (among
other products) methane, ethane, propane, and
butane. This type of change is called thermal
cracking. Among the reactions that take place are
the following:CH3CH2CH2CH2CH3 CH3 + CH3CH2CH2CH2
CH3CH2CH2CH2CH3 CH3CH2 + CH3CH2CH2
CH3 + CH3 CH3CH3
CH3 + CH3CH2CH2CH2CH3
CH4 + CH3CH2CH2CH2CH2
CH3 + CH3CH2 CH3CH2CH3
CH3CH2 + CH3CH2 CH3CH2CH2CH3
(a)
For which of these reactions would you
expect Eact to equal zero?
(b)
To be greter than zero?
(c)
To equal H?

25

DPP NO-17
1.
ORGANIC chemistry
Time: 15 minutes
Compound
Number of monochloroproduct
Number of monocloroproduct
(excluding stereoisomer)
1.
2.
3.
4.
5.
6.
7.
8.
9.
CH2
2.
1.
Compound
S
.
J
.
Number of Dichloroproduct
(including stereoisomer)
1.
1-chlorobutane
2.
R-2-chlorobutane
3.
3-chloropentane
4.
R-2-chloropentane
5.
S-2-chlorobutane
6.
R & S-2-chloropentane
7.
R & S-2-chloro butane
r
i
Optically active product

26
ORGANIC ChemIstRy
Question bank on
r
i
GRIGNARD'S REAGENT
H
N,
RC
O
RCOR, H2
HCOOEt
SiCl
4
l2
PbC
Cl 2
Zn
H2 O
,
S,
CH
RMgX
O
+
gB
r
O
+
O
, H 2O
CH 2
CH 2
O
, H2
HO
RC
O2, H2O,
O
+
O
+
O
,H
CdCl 2
S
.
J
.
X
2
CH
H=
C
2
H
CIC
R
CICH 2O
RMgX
PhC
H2 C
l
CI
CN
Cl 2
Br2
I2

27
GRIGNARDS REAGENT
Q.1
The order of reactivity of alkyl halide in the reaction

R X + Mg RMgX is
(B)
(A) RI > RBr > RCl
(B) RCl> RBr > RI
(C) RBr > RCl > RI
(D) RBr > RI > RCl
Q.2
Mg
BrCH2CCCH2Br
BrMgCH2CCCH2 MgBr
O
||
PhMgBr(excess) + CH3 C Cl
(C)
O
O
||
||
CH3MgBr(excess)+ CH3 C O C CH3
(D)
O
||
CH3MgBr (excess) + Cl C O Et
H
(excess)
Et 2O
Mg(1 eq.)
Et2O
Product
Cl
Q.9
The major product is

(A) Br MgCH2 C C CH2Br
(B) Cyclobutyne
(C) (CH2C C CH2)n
(D) CH2 = C = C =CH2
Q.3
Q.4
1 equivalent Mg
Br
ether
Br
(D) None of these
S
.
J
.
Which of the following reacts with Grignard reagent

to give alkane?
(A) nitro ethane
(B) acetyl acetone
(C)
acetaldehyde
(D) acetone
r
i
Y ; Y is
(B)
D
D
(C)
D O
Cl
(A)
On conversion into Grignard followed by treatment

with ethanol, how many alkyl halides (excluding Q.10
stereoisomers) would yield 2- methyl butane
(A) 2
(B) 3
(C) 4
(D) 5
Compounds are shown with the no. of RMgX

required for complete reaction, select the incorrect
option
(A) CH3COOC2H5
1
(B) CH3COCl
(C) HOCH2COOC2H5
OH
Q.5
How many litres of methane would be produced

when 0.595 g of CH3MgBr is treated with excess of
C4H9NH2
(A) 0.8 litre
(B) 0.08 litre
(C) 0.112 litre
(D) 1.12 litre
(D)
CHO
COOC2H5
Q.11
Q.6
How many litres of ethene would be produced when

2.62 g of vinyl magnesium bromide
is treated with 224 ml of ethyne at STP
(A) 0.224 litre
(B) 0.08 litre
(C) 0.448 litre
(D) 1.12 litre
MgBr
Q.7
OH
(B)
(C)
H
H
C = O (II)
CH3
(A) I > II > III > IV

(C) II > I > IV > III
C = O (III)
CH3
CH3
C = O(IV)
Me3C
C=O
Me3C
(B) IV > III> II> I

(D) III > II> I > IV
Carbonyl compound (X) + Grignard reagent (Y)

OH
OH
(A)
What will be the order of reactivity of the following

carbonyl compound with Grignards reagent?
(I)
Q.12
OPh
(D)
Ph X, Y will be-
Me
Et
O
O
||
||
Et
Ph,
MeMgBr
Me
C
Ph,Et MgBr
(A)
(B)
Q.8
(A)
In which of the following reactions 3 alcohol will be

obtained as a product.
O
||
MgBr (excess) H C Cl +
H
O
O
||
||
(D) Me C Et,Ph MgBr (D) Et C Ph,Et MgBr

28
Q.13
(i) Mg
(R) 2Bromooctane
X; X is
C6H13
*
(A) CH3
COOH
(B) HOOC
(D) None of these
(A)
(B)
CH 2CH=O
(C)
CH=O
(D)
CHCH3
|
CH=O
Br
1. Mg/ether
Product (s)
+
2. CH3CHCH2CH 3. H3O
|
||
OH
O
(B) RMgX + C2H5OH Alkane
Select the product from the following
(C) RMgX + CH3CH2Cl Alkene
I.
(D) RMgX + Cl
Ether
The number of
consumed
per
moles
mole
of
of
COOEt
is
(A) 4
(B) 2
(C) 3
Q.20
Br
Dry Ether
O
||
CH3CCH3
NH4Cl
X
(Major)
End product of above reaction is
(A)
CH 2
||
CH2= CH CH2 C CH 3
(B) H2C CH CH C CH3

|
CH3
OH
|
H
C
CH
CH
C
CH3
(C) 2
2
|
CH3
2OH
(D) H2C = CH CH2CHCH
|
2CH3MgBr
A. Product A formed
(A) is ethyl acetate

(B) further react with CH3MgBr/H2O+ to give acetone
(C) further react with CH3Mg Br/H2O+ to give t- butyl
alcohol
(D) Can give pinacol when treated with Mg followed
by H2O
Order of rate of reaction of following compound with
phenyl magnesium bromide is
O
||
Me C Cl
I
(A) I > II > III

(C) III > I > II
Q.22
O
||
C2H5 O C OC2H5
S
.
J
.
(D) 1
Select the correct statement :

(A) 1, 4- dibromobutane react with excess of
magnesium in ether to generate di-Grignard
reagent.
(B)1, 2- dichlorocyclohexane treated with excess of
Q.21
Mg in ether produces cyclohexene.
(C) Vicinal dihalides undergo dehalogenation to
give alkene when heated with Zn dust or Mg.
(D) 1, 3- dichloropropane by treatment with Zn dust
or Mg forms cyclopropane.
Mg
2
CH3CH = CH2

r
i
II. CH 3 CHCH 2CH III. CH 3 CHCH 2CH

|
||
|
|
OH
OH
O
OH
(A) III
(B) I, III
(C) I, II
(D) II, III
grignard reagent
the
compound
Q.17
H3 O
O
||
CCH3
In which one of the following reaction products are

Q.19
not correctly matched in
(A) RMg X + CO2
Carboxylic acid
( 2) H
HO
Q.16
followed
Product
CH3
(C) A and B both
Q.15
OEt
OEt
OEt
Ethyl ortho formate
C6H13
Q.14
MgBr + H C
Q.18
(ii) CO2
(iii) H
O
||
Me C O Et
III
(B) II > III > I

(D) II > I > III
Select the correct order of decreasing reactivity of

the following compounds towards the attack of
Grignard reagent
(I) Methyl benzoate
(II) Benzaldehyde
(III) Benzoylchloride
(IV) Acetophenone
(A) II > III > I > IV
(B) I > II > III > IV
(C) III > II > IV > I
(D) II > IV > I > III
O
Q.23
CH3 MgX
NH4 Cl
(A) Enantiomer
(C) Meso
Q.24
O
||
Me C H
II
Product is
(B) Diastereisomer
(D) Achiral
Nucleophilic addition of Grignard reagent cannot

occur in
(A)
CH3
(C)
O O
O
O
|| ||
||
||
CH 3 C CCH 3
(B) CH3 C CH2CCH3
O
O
O
||
||
CH 3 C CH 2CH 2CCH 3
(D) O

29
Q.25
CH3 CCH2CH2 CH2 Cl CH3MgBr A, A is

||
O
CH3
|
(A) CH3 CCH2CH2CH2Cl
|
OH
Q.26
Q.30
(D)
A,
(ii) H3O
HO OEt
(A) CH3CCH2CH2COCH2CH3 (B) CH3CCH2CH2CCH 3

CH3
O
OH
OH
Cl
NH4 Cl
Identify P1 & P2.
(D) CH3CCH2CH2CCH3
O
H 3C
Q.27
CH3
(A) CH4
(B)
S
.
J
.
CH CHO
Mg
2
3
PhCH3
(A)
(B)
(C)
h
NH4 Cl
ether
OH
CH2 CH
CH3
(A)
CH3
CH3
(C)
OH
CH
(B)
Q.33
CH
CH3
r
i
HO Me
(C)
(D)
O
14
Mg
NaHCO
(i) CO
(A)
(C) gas
(B)
3
(ii) H /H2 O
(i) CH ONH
3
2
2CH3MgBr
(ii) H
CH3
CH3
following
Product C is
(A) CO
(B) 14CO2
(C) CO2
14
(D) A mixtue of CO2 and CO2
CH3
OH
C
(D)
HO
Br
Q.32
CH3
the
2CH3MgX
P 1 + P2
Q.31
CH3
H 3C
RMgX (2 moles)
Deprotonation will occur from

positions:
(A) 1, 2
(B) 1, 3
(C) any two positions (D) 1, 4
A formed in this reaction is
(C)
OH
(i) CH3MgBr(one mole)
CH3
CH
(4)
OH
CH3
(2)
OH
H
(1) S
H3C
CH 3CCH 2CH2COCH 2CH 3
CH3
CH3
O (3)
H
CH3
O
CH3
HO
(D)
OH
(B) CH3 CCH

2CH2CH2CH3
||
CH3
CH3
CH3 ,
(C)
H3C
(C)
HO
(A) CH3 O NH CH3 (B) CH3 NH CH3

(C) CH3 NH2
(D) CH3 OH
OH
Q.28
Select the correct order of reactivity towards Q.34

Grignard reagent for nucleophilic attack.
O
O
||
||
(A) R C R R C H
(B) Cl CH 2 C H CH 3CH 2 C H
||
||
O
O
O
||
O
||
NO2 < CH3 C O
(C) CH3CO
Q.35
(ii) H / H2O
CH3
(A) The product is optically active

(B) The product contains plane of symmetry
(C) The product shows geometrical isomerism
(D) The product shows optical isomerism
Which of the following is incorrect.
O
O
CH3MgX
CH C OC H
(A)
O
O
||
||
(D) R C OR R C NR 2
Cl
OC2 H5
(1 eq)
OC2H5
C2H5MgX
(B) CH3 C OC2H5

CH3C OC2H5
OC2H5
(i) CH3MgBr / CuCl
(X) Major + (Y)
Q.29
(i) CH MgBr
(A)
(X) and (Y) respectively are
H3 O
(C) CH3MgX + C = S
CH3C SH
(A)
,
CH3
CH3
(ii) H2O / H
OH
(1 eq)
OH
(B)
,
CH3
CH3
OH
O
H3 O
(D) CH3MgX + C = O
CH3C OH

30
Q.36
Which reaction gives 1 aromatic amine as major Q.41

product.
Br
(ii)NH4Cl
NH4 Cl
(A) 1ROH
(C) 3ROH
NH3
Mg/ ether
(A)
(i)CH CN
RMgX
3
RMgX
(A)
(B) will be
(B) 2ROH
(D) Alkene
Br
NH3
Mg/ ether
(B)
Q.42
F
Br
Hg(OAc )2
(D) HOCH2CH2CH2CH2 OH
CH3MgBr + CH2 = CH C H
H O
Product (1, 4
addition). It is
Q.43
OH
(A) CH2 CH
C
CH3
(A) CH4 + IMgO
OH
C CH3
(D) None
(B) CH3O
C CH3
S
.
J
.
OMgI
(i) PhMgBr
Product
Q.38
(C) CH3C
(ii) NH4 Cl
OH
CH3
Me
MgI
Produtcs in this reaction will be

(A) Stereoisomers
(B) Enantiomer
(C) Diastereomers
(D) Geometrical isomers
(D) CH3O
Q.44
CH3MgBr (1 eq.)
CCH3
r
1
+ Ph Mg Br
Ph CH2CH2OH
(i)
2
+ Ph Mg Br
Ph CH2CH2CH2OH
(ii)
The product is:
(A) r2 > r1
(C) r1 = r2
OH
(A)
Q.39
r
i
The reaction of 1 mole each of p-hydroxy

acetophenone and methyl magnesium iodide will
give
(B) CH2 CH = CH CH3
(C) CH3CH2CH2CHO
N
(B)
OH
O
(C)
Q.40
OH
CH3
NH3 /NaBH4
Q.37
(B) CH3 CHCH2CH3
CH3
CH
CHCH3
3
(C)
(D) Ph
(ii)H2O
O
(A) CH3 CHCH2OH
NH3
Mg/ ether
(C)
(i)CH3MgCl
CH3 CH CH2
Q.45
(B) r1 > r2
(D) r1 = 2r2
How many moles of Grignard reagent will be

required by one mole of given compound?
SH
HO
O
C
OEt
Cl
(D)
(i) Br
CH2
(A) 7
(ii) CH3MgBr
(2equi.)
CH3
(B)
CH3
CH3
(C)
Q.46
Cl
2
CH2= C = O
C4H8O
(A)
CH2
CH3
(B) 6
(C) 8
(D) 5
Consider the given organometallic compound.

(I) (CH3)2Hg
(II) (CH3)2Zn
(III) (CH3)2Mg
(IV) CH3Li
The correct decreasing order of ionic character is
(B) II > I > III > IV
(C) I > III > II > IV
(D) IV > III > II > I
(D) All of these
CH2

31
(i) CH3MgBr
Q.47
CH3CH = CH C CH3
For Q. no. 48 to Q.no.50

Consider the given reaction and answer the
following questions
(ii) H3O
(i) CuI CH3MgBr

(ii) H3O+
COOCH3
MeMgBr
Products
OH
(A) P is CH3CH = CH C Me Q is CH3CH CH2 C CH3
OH
(B) P is CH3CH CH2 C CH3 Q is CH3CH = CH C Me

CH3
Me
Q.48
No. of RMgX consumed in the reaction is

(A) 4
(B) 5
(C) 6
(D) 7
Q.49
How many product will be formed in given reaction

(excluding stereo)
(A) 2
(B) 3
(C) 4
(D) 5
Q.50
Which of the following reaction will give the same

Hydrocarbon formed as one of the product in the
above reaction.
(A) EtMgBr + Me OH
(B) PhMgBr + Me OH
(C) MeMgBr + Ph OH
(D) MeMgBr + CH3 CHO
(C) P is CH3 CH=CHC(CH3)2 Q is (CH3)2CHCH2C CH3

OH
(D) P is (CH3 )2CHCH2C CH3 Q is CH3CH=CHC(CH3)2

O
CH3
Me
(excess )
OCH3
SH
OH
S
.
J
.
ANSWER KEY
R CH2 CH Me
RMgX
HO
O
+
R CH2 CH2 OH
H
N,
RC
R4Si
SiCl4
l2
PbC
HC
OO
Et
R CHO
Cl 2
Zn
PbR4
2
CH
H=
C
2
H
CIC
CICH2OR
RMgX
CIC
OO
Et
CI
CN
N
5
C
20
C,D
35
B
50
C
R2CHOH
H2
=C
CH
CH 2
R
OR
RCH2
RCOOEt
I2
Br2
RCN
R2
R C R
4
A,B
19
C
34
B,C
49
C
OH
R 3C
Cl 2
OH
3
C
18
C
33
C,D
48
C
R,
RCO
RR
Zn
R2 C= O
2
D
17
B
32
C
47
C
O
, H2
HO
RC
HO
HC
O
+
H
gB
r
RSH
O
+
R2Hg
OH
CH
2
ROH
HO
2
,
O
+
R C OH
Q.No.
1
Ans.
A
Q.No. 16
Ans. A,C,D
Q.No. 31
Ans. A,B
Q.No. 46
Ans.
D
HO
,H
R 2Cd
H
H 2O
RC
S,
RH
l
CdC 2
R C SH
RH
O2, H2O,
RSO2H
S
r
i
RCl
RBr
RI
RC
6
C
21
A
36
B
7
A
22
C
37
C
8
9
B,C,D D
23
24
A
B,D
38
39
A,C,D D
10
A
25
C
40
A
11
A
26
C
41
C
12
A,B,C
27
A,B,C
42
B
13
C
28
B
43
A
14
C
29
B
44
B
15
A
30
A
45
A

32
ORGANIC chemistry
DPP NO- 01
Time: 15 minutes
Explain:
CH2N2
CH2 = CH2
CH2N2
CH CH
2.
Characteristics :
1.
The reaction is stereospecific in nature
Q.1
Simon Smith Reaction:

CH2I2
CH2 = CH2
CH2 CH 2
CH2I2
Zn
CH2
OH
Zn Zn+2 + Ze
1)
2e
I CH 2 : +
I CH2 I
1.
Zn+2
4.
OH
S
.
J
.
COH

H
SOCl 2
3.
N +
+ HCl
S=O
Cl
OSO
+
Cl
N
:
Cl
Cl
R :O
ROSO
S=O
H
N +
Cl
:O: +
Cl
+
OSO
Cl
S=O
Cl
2.
S
O
+
Cl
O
+
R O S Cl
O
Cl R
Cl
R
+ Cl
+ HCl
Cl
Cl
R O S Cl
R Cl + SO2
Machanism:
1.
Cl
Cl
Time: 15 minutes
This reaction leads to inversion of Configuration.

Darzens Process.
Cl
(Kolbe Schmidt Reaction)
ORGANIC chemistry
+ Cl
:O: +
OH
R Cl + SO2 + HCl
Mechanism:
1.
R
O
C
DPP NO- 02
r
i
OH
CO2
NaOH
high P
high T
CH2 Zn I
(Carbenoid)
CH2I2
Zn
2.
CH2I2
Zn
3.
Zn/ Cu
Mechanism:
(No bond rotation)
CC
ZnI
N:
1.
C=C
2.
O S Cl
R Cl + Cl S
Cl
S
OH
+
O
: H
So2 + Cl
H Cl +
SO2

33
Note:
the reaction leads to selection of configuration

Retention of configuration.
For example:
O
Q.1
H
:
CH3
C CH
SOCl2
OH
C CH = C = O
CH3
C
Ph
Ph
CH3
SOCl2
Ph
Arndt Eistert Reaction:
Q.2
CH2N2 R C CH 2 N 2
SOCl2 R C Cl
R C OH
SOCl2
C OH
Ag2O/
CH3
CH 3
R CH 2 C
OH
OH
SOCl2
RC
H
CH 3
OH
SOCl2
Nucleophilic addition elimination:

O
N:
1. SOCl 2
2. CH 2N 2
RCH = C = O
3. Ag2 O/
O
4.
H
H
S
.
J
.
(Overall)
R CH 2 C
OH
Characteristics:
1.
The reaction is known as homologation
2.
The reaction occurs with relation of configuration.
CH2N2
R C CH 2 N
R C Cl
r
i
SOCl2
Ph
O
Ph
Q.3
+ Cl
Ex.1
Mechanism:
+
CH2 = N = N:
1.
N:
Ag2O -- -
R C CH= N =N:
H
OH
---
COOH
+
R C Cl + :CH 2 N
O
+
R C CH 2 N
N:
Cl
O
+
R C CH 2 N
Wolf Rearrangement:
O
+
R C CH 2 N
Ag O/
2
N:
Mechanism:
1.
2.
N:
1. SOCl 2
2. CH 2N 2
2. Ag 2O
4. H2O
N:
+ Cl
Nucleophilic addition:
1.
OH
OH
+
R C CH N
+
Ag2O/
N: R C CH N
N:
R CH C
OH
O
OH /H O
2
R CH = C = O
R CH 2 C
1.
HOH R CH C
+OH
OH
2.
R C CH
+N
ROH/RO
R CH = C = O
NH2 / NH 3
R C CH O = C = CH R.
3.
R CH = C = O
4.
R CH = C = O
2.
+
:CH 2 N
RNH2

34
Diazo methane
Acid-Base Reaction:
1.
O
5.
CH2N2 + HCl CH3Cl + N2
CH2N2
EtCH
- - - - - - - + - - - - - - - - ---
2.
CH3 O
R OH + CH2N2
6.
1. SOCl 2
CH3 CH2 C C OH
2. CH 2N 2
3. Ag2 O/
O
4.
H
H
3.
+ CH2N2
R C
--------
OH
7.
4.
3. Ag 2O/
COOH 4. H2 O
+ CH2N2
CH 3
8.
O
OH
Homologation Reaction:
O
S
.
J
.
H
CH3 O
O
2.
CH2N2
RCR
- - - - - - - - + - - -- - - - - - - -
CH2N2
CH2N2
DPP NO- 03
Nitrenes :
Fill in the blanks:
12.
CH2N2
EtCCH3
- - - -- - - - + - - - - - - - - ---
- - - - - - - + - - - - - - - - ---
+
R N = N = N:
(a)
ORGANIC chemistry
(d)
h
R S N = N = N:
ROCNOS
O
(e)
H N = N = N:
+
h
RC N = N = N:
+
O
- - - - - - - - - - - + - - - - - - - - - - - - - - (gas)
- - - - - - - - - - - + - - - - - - - - - - - - - - (gas)
(f)
R O C N = N = N:
+
O
- - - - - - - - + - - - - - - - - - - (gas)
+
O
- - - - - - - - - - - + - - - - - - - - - - - - - - (gas)
(c)
NO2
Time: 15 minutes
- - - - - - - - - - - + - - - - - - - - - - - - - - (gas)
- - - - - - - - - - - + - - - - - - - - - - - - - - (gas)
(b)
--------------
2. CH 2N 2
3. Ag2O/
4. OH/H 2O
CH2N2
EtCH
- - - - - - - - + - - - - - - - - - ---

Q.1
1. SOCl 2
- - - - - - - + - - - -- - - - - -- -
11.
4.
COH
Cl
3.
10.
r
i
--------------
COOH 2. CH 2N 2
3. Ag2 O/
4. RO/H 2O
CH2N2
RCH
RCCH2 H + RCCH2
--------------
1.
1. SOCl 2
9.
1. SOCl 2
2. CH 2N 2
CH2 CCl 3. Ag2O/
4. OH/H 2O
+ CH2N2
CH3 C
--------
5.
1. SOCl 2
2. CH 2N 2
No 2
O = COH

35
Fill in the blanks:
H N = C = O
(g)
- - - - - - - - - - - + CO _ _ _ _
KOH R NH2
Br2
RCN
D
Mechanism:
(h)
OH
R N O S Ph
1.
H
O
----------- -
R C N
HOD + R C N:
D
+ OH
D
NO2
BrBr
OH
N Cl - - - - - - - - - - - O
R C NBr
:
HOD +
RC N Cl
(j)
OH
----------- -
OH
Br + _ _ _ _ _ _ _
Hoffmann Bromanide Reaction:
NaOH
R NH2 + KBr + k2CO3
R C NH 2 + Br2
2.
S
.
J
.
RN=C=O
Mechanism:
1.
O
RCNH
R C N: +
OH
RNC
: :
OH
r
i
Wolf
Rearrangement
RN=C=O
RNC
(i)
OH
CO2 + _ _ _ _ _ _ _ _ _ _ _ _
H2 O
Br Br
OH
O + R C N:
R C N H
Br
Br
r.d.s.
RN=C=O
OH
R N=C=O
Q.1
15
(a)
RNC
R NH 2 + OH
O = C NH 2
Br2 /KOH
- - - + - -- -
(b)
Br2 /KOH
------ ---- -R C N Ph
H
Q.3
O
(a)
(iv)
RNC
H
C NH 2
OH
:
R N + CO 2
(ii)
O
Fill in the blanks:

O = C NH 2
C NH 2
CH3
(iii)
C NH 2
O
CH3
C NH 2 Cl
Q.2
Compare rate of reaction:

O
(a)
: :
:
+ Br
(i)
O
O
R C N:
+ Br
R NH 2 + OH
CH2 CH 2 C NH 2
Br2 /KOH
- - -- -

36
(b)
O = C NH 2
Me
Et
Br2 /KOH
- - - -- - - - - - - - -
Mechanism:
1.
R
R
+
C=N
H
l
(c)
NH
C=N
OH
O
+
Br2 /KOH
------- ---- --
H
r.d.s.
R
l
Br2
------ --KOH
(d)
Ph
H
O
CONH 2
H
(e)
Br2
------ ---- -KOD/D2O
CH3
(g)
R CND 2
C=N
Ph
C=N
C NH 2
CH3
(i)
-----------
CH3
C=N
OH
OH
N
O
C=N
Q.5
C NH 2
Br2
- - - - - - - - - - NaOH
Q.6
C=N
R C NH R
(a)
Catalyst:
O
Et
OH
Ph
C=N
H2SO4
Ph C N
S Cl
Migration of R is always from anti position.
H - - - - - - - - - -
Q.7
Explain:
OH
H2SO4, SOCl2, SO3, PCl5, P2O3, PCl3, BF3,
H
CH 3
Beckmanns Rearrangement:
(Catalyst)
OH
C=N
Br
H - - - - - - -
O2 N
CH3
2
------ ---- -NH2 CNH2
NaOH
PCl5
OH
CH3
-----------
KOBr - - - - - - - - - - -
CH3
(k)
CH3 C C NH 2
(j)
PCl5
CH3
CH3
-----------
KOBr - - - - - - - - -
Q.4
Br
H2SO4
OH
CH3
Q.3
(h)
OH
S
.
J
.
Br2
------ ---- -KOH
r
i
H2SO4 Ph C NH CH 3
Ph
Q.2
Q.1
R CNH 2
+ OH
OH
O
(f)
Rl C = N
NaOCl - - - - - - - - - - -
EtCNH2
Tautomer
Rl C = N R
: :
R C = N
+
OH
Ph
(b)
C=N
HO CH2
H2SO4 PhC N+ H

37
ORGANIC chemistry
DPP NO- 04
Time: 15 minutes
Schmidt Reaction:
H2SO4
R C OH + HN3
RNH2 + CO2 +
N2.
Curtius reaction:
O
O
NaN3
RCN=N=N
R C Cl
O
NH2 NH2
R C O CH 2 CH 3
O
O
HNO2
R C NH NH 2 R C N = N = N:
+
O
Mechanism:
1. NaN3 RN=C=O OH/H2O
R NH2
R C Cl
2.
R C OH
Imp.
O
RN=C=O
N2
H OH /
R NH2 + CO2
Et O
C OH
R C N = N = N:
H
S
.
J
.
H+
H2O
_ _ _ _ _ _ _
_______
Q.2
R C N = N = N:
:
C Cl
Q.1
NaN3
_______
RC
HN = N = N:
NHR
HOH R NH + CO
R N = C = O
2
2
+H
R/ OH RNH C OR 1
R N = C = O
O
RNH2
R N = C = O
RN C
H
r
i
O
NaN3
SOCl2
_ _ _ _ _
CH3
_ _ _ _ _
_ __ __ _
_ _ _ _ _
H2O/
CH 3
Q.3
O
C
_____ R
NaN
1. NH NH
2. HNO2
H/
O
CH3 O
CH3
COH
N3H(H2SO4 )/
_ _ _ _ _ + _ _ _ _ _ _ +_ _ _ _ _ _
2
2
CH2 COC2H5
_ _ _ _ _ + _ _ _ _ _ _ +_ _ _ _ _ _
Q.2
H _____
____ H
_ __ __ _
Q.5
CH2 COH
N H(H SO )
3
_ __ __ _
Cl
O
Q.4
Q.1
Schimidt miscellaneous:
O
____
H
R C R
R C N R
N3H/
H
1. NH2 NH2 _ __
COCH 2CH 3
2. HNO2
_ _ _ _ _ H O H/ _ _ _ _ _

38
Mechanism:
1.
+H
HN = N = N:
R
RCNOCR
H
OH
: :
OH
Mechanism:
1.
+ OH
H
O + RCN OCR
RCR
:
HN = N = N:
OH
OH
RC
N2
HN = N = N:
:
H
+
H + RCNR
Q.2
Lossens Rearrangement:
O
R C N O C R
H
+O CR
O
O
KOH _ _ _
CH2 C N O C Ph
Q.1
RCN
RCR
O
RN = C = O
: :
R NH 2+ CO 2
OH
RNH2+ R C O
C N O C
CH3
S
.
J
.
r
i
CH3
KOH

39
ORGANIC chemistry
r
i
S
.
J
.
Reaction
Intermediates

F-106, Road No. 2, Indraprastha Industrial Area, End of Evergreen Motors (Mahindra Showroom), BSNL Office
Lane, Jhalawar Road, Kota, Rajasthan (324005)
40
Q.1
Q.2
EXERCISE I
2-Chloropentane on halogenation with chlorine
gives 2,3-dichloropentane. What will be the
structure of free radical species formed in the
reaction?
(A) Planar
(B) Trigonal planar
(C) Square planar
(D) Pyramidal
Decreasing order of nucleophilicity
following nucleophile is :
(1) CH3O
of
(B)
H
(C)
the
OH
(D)
(2) C N
O
S
(3)
r
i
S
.
J
.
(B) 1 > 2 > 4> 3

(D) 1 > 2 > 3 > 4
(A)
The correct order of rate of Wurtz reaction.

Na
(I)
CH2 F
CH CH
2
ether
Na
CH2 Cl
(III)
(B)
CH2 CH2
ether
Q.8
What will be the major product, when 2-methyl

butane undergoes bromination in presence of
light?
(A) 1-bromo-2-methyl butane
(B) 2- bromo-2-methyl butane
(C) 2- bromo-3-methyl butane
(D) 1-bromo-3-methyl butane
Q.9
Which can not be the possible product of the

given reaction
CH2 CH2

(B) II > I > III > IV
(C) IV > III > II > I
(D) In all rate of Wurtz reaction is same
Q.4
CH3 CH CO2K
electrolysis
(A) (Major)
CH3 CH CO2K
Major product (A) of above reaction
Q.5
(A)
(B)
(C)
(D)
Mg
H2O
P1
P2
(A) It is a spiro compound

(B) It is a Ketone
(C) It can show tautomerism
(D) It is an alkene
Q.6
Consider the following reactionO
OEt
Na/ether
FeSO4 + H2O2
liq. NH3
Fenton's
reagent
the major product P is:

O
(A)
OH
CCl4,
Product (s)
N
H
Br2
CH3 CH2 C OAg
(A) CH3 CH2 Br

(B) CH3 CH2 C O CH2 CH3
Which of the following is not correct about P2.

O
(C)
(D) None of these
Na
Na
ether
CH2 I
CH2 CH2
ether
CH2 Br
(IV)
(X)
X is :
(A) 4 > 3 > 2 > 1

(C) 2 > 1 > 3 > 4
(II)
Na/ether
CCl4. Peroxide
Q.3
NBS
Q.7
(4) CH3 C O 2
(C) CH3 CH2 CH2 CH3

(D) CH3 CH2 CH3
Q.10
Pick the correct statement for monochlorination of

R-secbutyl Bromide.
Me
H
Br
Cl2
300C
Et
P
(A) There are five possible product; four are

optically active one is optically inactive
(B) There are five possible product; three are
optically inactive & two are optically active
(C) There are five possible product; two are
optically inactive & three are optically active
(D) None of these

41
Q.11
Correct order of rate of photochlorination for Q.16

following compounds is
(A) I is more soluble than bromocyclopropane

(B) I gives pale yellow ppt. on addition with
AgNO3
(C) I is having lower dipole moment than
bromocyclopropane
Br
(D) I is more ionic than
CH3
C
CD3 CD3 CH3
CH3 CH3
CH3
CH3
(I)
(A) II < I < III
(C) III < I < II
Q.12
(II)
(III)
(B) I < II < III
(D) II < III < I
Which one of the following carbocation would you

expect to rearrange.
KNH2
(A)
(A)
(C)
(D)
r
i
S
.
J
.
NH2
(B)
(C)
Q.18
How many, 1,2-Shifts are involved during the

course of following reaction:
OH
(D) (B) and (C) both
conc. H2 SO4
Which of the following carbocation is most stable?

CH3
(A) 1
(B) 2
(C) 3
(D) 4
CH3
+
C
CH3
H3C
+
C
(B)
CH3
CH3
+
C
CH3
(D)
CH3
Q.19
(X)
OH
Product (X) is:
CH3
OH
CH3
HO
CH3
CH3
H3C
OH
(C)
(B)
CH3
NH2
NH2
(A)
CH3
CH3
Cl
NH3
Q.13
Q.17
Product can be
, which is not the correct statement
Br
(A)
(B)
CH3
Q.14
Which carbocation is least likely to form as an

intermediate?
(A) (C 6H5 )3 C
(B)
(C)
Q.20
(C)
Q.15
(D) CH2 CH
For the reactions

(I)
Cl
(II)
Cl
(III)
(IV)
(D)
(I)
OH
(III)
OH
+ Cl , H1
(A) I < II < III < IV

(C) I < III < IV < II
+ Cl , H2
Among the given

dehydration order is:
compounds,
the
(II)
OH
(IV)
OH
correct
(B) II < III < IV < I

(D) I < II < III = IV
OH
CH2Cl
CH2 + Cl , H3
Cl
+ Cl , H4
The correct decreasing order of enthalpies of

reaction for producing carbocation is:
(A) H1 > H2 > H3 > H4
(B) H4 > H1 > H2 > H3
(C) H3 > H2> H1 > H4
(D) H2> H1> H4 > H3
Q.21
P. The product P is
5C
(A)
(B)
(C)
(D)
OH

42
Q.22
Rate of dehydration when given compounds are

treated with conc. H2SO4.
Q.26
OH
H+
OH
CH2OH
(P)
CH3
(Q)
(A)
(B)
(C)
(D)
OH
OH
CH3
CH3
(R)
(S)
(A) P > Q > R > S

(C) R > Q > P > S
(B) Q > P > R > S

(D) R > Q > S > P
Me
Q.27
Conc.H2SO4
Me
OH
H2SO4
Q.23
OH
OH
Product 'A' is-
r
i
S
.
J
.
(A)
Me (B)
Me
Me
Me
'X' is
Me
OH
OH
(A)
(C)
(B)
C Me
Me
(D)
Me
Q.28
OH
(C)
How many products are obtained in the given

reaction:
Et
(D)
Ph
HO
OH
OH
Et
OH
Q.24
CH3 H+
CH3
O
Q.29
(B) O
Q.25
CH3
N
(D) OH
CH2
O
CH3
CH3
Ph
(B) 2
H2SO4
OH
Ph
(C) 3
H3O
CH3 CH C CH2 NH2
CH3
CH3
HO
HO
(D) 4
CH3
(A)
(C)
Ph
CH3
CH3
CH3
(A) 1
major product is
CH3
HNO2
(X)
CH3 CH3
(major)
Major product of above reaction is:
CH3
CH3
(A)
CH3
CH3
CH C CH2 OH
CH3
A, A is
(B)
OH
CH3
(C)
(D)
OH
OH
OH
HO
(A)
Q.30
Which will dehydrate at fastest rate by H3PO4 :

(A) 2-methyl butane-2-ol (B) 3-methyl butane-2-ol
(C) Butane-1-ol
(D) 2-methyl butane-1-ol
Q.31
What is the order of reactivity with HBr.
(B)
CH3
OH
CH3
OH
OH
OH
(C)
(a)
(D)
OH
OH
(b)
(c)
CH3O
CH3O
OH
(A) a > b > c

(C) c > b > a
(B) b > a > c

(D) b > c > a

43
CH2 = CH3
Q.32
HBr
CCl4
Cl
Q.38
Stability order of following singlet halocarbene is

(A) CF2 > CCl2 > CBr2 > CI2
(B) Cl2 > CBr2 > CCl2 > CF2
(C) CCl2 > CF2 > CBr2 > CI2
(D) CF2 > CI2 > CCl 2 > CBr2
Q.39
Trans-Butene-2 3 Product
CH3
What is stereochemistry of product?

(A) Racemic mixture
(B) Optically inactive
(C) Diastereomers
(D) Meso product
Q.33
CHCl / KOH
Solvent
In the given reaction :
Cl
H
Br2
(A) CH3
[X]
[X] is :
H
N
Br
(A)
Br
(C)
Br
Br2
Products
Cl3C CH = CH2
(A)
(C)
H3C CH = CH2
The order of rate of reaction of following towards

carbylamine reaction:
O CH3
Q.37
CH2 = CH CH3
Mg / ether
NH2
NaOH
(i) CHCl / KOH
CaO /
(ii) H3O
Y.

X 3
COOH
(D) None of these
OMe
OMe
(A)
NBS
14
NH2
OMe
O
1
NH2
(iv)
Identify X and Y :
(B) CH3 C CBr3
(C) CH3 CH2 C CI3
(iii)
NH2
(ii)
NO2
CH3
(A) (ii) > (i) > (iii) > (iv) (B) (ii) > (iii) > (i) > (ii)
(C) (iv) > (i) > (iii) > (ii) (D) None
(A) CH3 C CCl3
(D)
(i)
Which of the following compounds yield most

Q.42
stable carbanion after rupture of (C1 C2) bond:
O
(B)
Cl
(I)
(II)
In addition of HOBr to (I) and (II)
(A) Br is at C2 in both cases
(B) Br is at C2 in II and at C1 in I
(C) Br is at C1 in II and C2 in I
(D) Br is at C1 in both cases
Q.36
CHCl Br
2
Product
Br
Q.41
Q.35
Br
(A) it is optically active (B) it is racemic mixture

(C) it is a resolvable mixture
(D) it is a mixture of erythro compounds
1
(D) Both (A) and (B)
Cl
CCl 4
CH3
Product is :
Br
Select the incorrect statement about the product

mixture in the following reaction:
Cl
KOH
Br
Q.34
CH3
Q.40
(D)
r
i
S
.
J
.
(C)
(B)
Cl
(B) CH3
CH3
Br
Cl
Cl
CHO
CCl4 / Peroxide
CHO
CH3
OMe
D O
2 Product(s)
Product(s) is/are :
14
14
(A) CH2 = CHCH2D (B) CH2 = CH CH2 D
(C) Both of these
(D) None of these
OMe
(B)
COONa
OMe
OMe
OMe
OMe
(C)
(D)
CHO
CHO

44
OH
MgBr
(i) CH MgBr
CHBr3
P1
P3
P2 3
Q.43
KOH
(ii)H /
HN
P. Identify P.
Q.47
H2SO4
OMe
P1, P2 and P3 are

OMe
OMe
(A)
OMe
NH
(A)
(B)
O
R
CHOH
OH
(C)
Me
OMe
OMe
(B)
OMe
Me2CH
Me
CHO
CHOH
conc .H SO
2
4

r
i
S
.
J
.
(A) Me2CH NH C Me
OMe
OMe
OH
C=N
Major product of this reaction is
Me
OMe
(D) Both (A) and (C)
O
NH
Q.48
OH
NH
(C)
OMe
OMe
(B) Me NH C CHMe2
CH= CH2
CHO
OH
OMe
(D)
Me
CHO
(C) Me C CH = N Me
CH= CH2
OH
(C) CH2 = C CH = N Me
h /
Q.44

P.
Me
N3
'P' is:
(A)
OH
(B)
Q.49
N=N
(C)
Chloride
(D)
N=N
P Toluene sulphonyl
P. 'P' is
(A)
N=N
(B)
NH
NH
NH2
Q.45
NH
Br
(C)
KOH
CH3CH2CH2NH2. Compound (X) is

O
(A)
CH3
(B)
(C)
OH
Cl
Q.46
(D)
Cl
COOD
Q.50
product is
OD
(A)
(B)
C2H5
C NH2
C2H5
OD
(B)
CH2OD
(C)
(C) Me C NH Me
HN
C2H5
CHO
NH
C Cl
Which of the following can not give Hoffmann's

bromamide reaction:
(A) Me C NH Br
(D)
CH3
Cl
3
2
(X) C4H7OCl
C4H9ON
(D)
C2H5
(D)
C2H5
NH
O

45
Q.1
EXERCISE II
Match the column :
Column-I
Column-II
(A) Electrophile (P) CH3 CH = CH CH3
(B) Nucleophile (Q) :CHCl
CH3
(C) Lewis acid (R) CH3 CH2

(D) Lewis base (S) Guanidine
(A)
Select the correct statements :

(A) Protonation increases electrophilic nature of
carbonyl group
(B) CF3SO3 is better leaving group than CH3SO3

(C) Benzyl carbocation is stabilized by resonance
(B)
CH3
H3C CH CH CH = CH2
CH3
(C)
H3C CH CH2 CH = CH CH3

CH3
(D) H3C CH CH = CH CH2 CH3
is unstable
r
i
S
.
J
.
CH3
OH
Q.3
CH3
H3C CH = CH CH
CH3
OH
(D) CCl3CH
Which of the following can be produced by Wurtz

reaction in good yield.
(A)
(B)
Q.8
Select correct statement about the product (P) of

the reaction :
H
Me
(C)
Q.5
(D)
Select true statement(s) :

(A) Instead of radical substitution, cyclopropane
undergoes electrophilic addition reactions in
sun light.
(B) In general, bromination is more selective than
chlorination
Q.9
(C) The2,4,6-tri-tert, butylphenoxy radical is
resistant to dimerization
(D) The radical-catalysed chlorination, ArCH3
ArCH2Cl, occurs faster when Ar= phenyl than
when Ar= p-nitrophenyl.
Q.10
Choose all alkane that give only one monochloro
derivative upon reaction with chlorine in sun light.
(A)
(B)
(C)
(D)
NBS
Q.6
(A) P is optically inactive due to internal

compensation
(B) P is optically inactive due to the presence of
plane of symmetry in the molecule
(C) The structure of P can have three optical
isomers possible
(D) P can have four possible optical isomers.
Products formed when HCl adds to 2,4-hexadiene
is:
(A) 4-chloro-2-hexene (B) 2-chloro-3-hexene
(C) 2-chloro-4-hexene (D) 1-chloro-2-hexene
HBr
In the given reaction C7H12 (A)
as major product
(B)
CH3
(D)
Which
of
following
reaction
CCl4
(B)
Br
Br
Br
(D)
Br
Q.7
Br
H3C CH2 CH2 CH2

OH
conc . H SO
4
2
X+ Y
(i) NaCN
(ii) H
CH3
(C)
(C)
are
CHO
Br2
CH3
(A)
(B)
Br
product
diastereomer of each other.
Br
(A)
CH2
CH =CH2
CH3
Q.11
CH3
Br
(A) can be
(C)
HBr
Br
(A)
(X)+(Y) enantiomeric pair.

CCl4 / h
Br / CCl
4
2
P
Me
Q.4
Product(s)
Product(s) are :
Q.2
(CH3 CH)2CuLi
NBS
CCl4 / peroxide
CH3
CH3
H
HBr
C=C
CCl4
(D) CH3 CH CH = CH Ph
HCl
peroxide
Et

46
Q.12
Which of the following can be formed during this Q.16
Which of the following will give cyclic products
reaction?
upon being heated or being treated by an acid?

O
H3O
(A)
OH
OH
OH
OH
(B)
(A)
OH
(B)
OH
OH
OH
(C)
(C)
(D)
r
i
S
.
J
.
O
(ii) ROH
(iii) RNH2
P1, P2 and P3 are :

(A) MeO
NH2
(B) MeO
Q.17
(C)
(D)
Which of the following reaction is not representing Q.18

major product.
O
OH
+
CH3
C NH CH3
CH3
H
(B)
14
Cl
CH3
(C) Ph C NH
2
O
(D)
14
PhLi
C= C
3-hydroxy propanoic acid forms Lactide on

heating
NH C NHR
C= N
succinic acid forms succinic anhydride on

heating
N= C = O
MeO
(A)
Select the correct statements.
(B)
Q.15
P3
propanoic acid on heating
NH C OR
(C) MeO
Q.14
OH
P2
(A) methyl malonic acid is converted into
(D)
P1
NaN3
C Cl
MeO
OH
(D)
(i) H2O
Q.13
OH
OH
CC
N
Br2
CH3 C CH2COOH
forms acetone on heating

Soda lim e
C5H8O4(A) C4H8O2(B) (C)
C is a hydrocarbon occupying 0.509 litre per g at

NTP approximately. Hence A and B are:
(A) methyl malonic acid, propanoic acid
(B) succinic acid, succinic anhydride
(C) Dimethylmalonic acid, 2-Methylpropanoic acid
(D) Ethyl Malonic acid, Butanoic acid
CH3
Q.19
Which of the following reaction is not incorrectly

formulated.
SO Cl
2
(A) CH2=CHCH3 2
CH2ClCHCl CH3
UV light
CH
Ph NH2
KOH
(B) HC CH + CH2N2 HC
HN3
H2 SO4
In which of following compound chiral center is
HC
NH2
N
H
photo
(C) (CH3)3CH+Cl2
(CH3)3CCl
ha log enation
as major product
not affected on heating.

(A)
CH3 CH COOH
OH
(B)
O
HOOC CH3
HCl
(D) CH3 C C H CH3 CH CH2

Cl
Cl
(C) CH3 CH CH2 COOH (D) CH3 CHCOOH

OH
CH2COOH

47
KNH
Q.20
Cl
Q.21
NH3 ,33C
Cl
KNH
liq. NH3
NH2
(A)
H2N
(B)
NH2
(A)
(B)
NH2
NH2
NH2
(C)
NH2
(C)
(D)
(D)
D
NH2
Q.22
This question consist of two statements, printed as assertion and reason, while answering this question you
are required to choose any one of the following responses.
(A) If assertion is true but the reason is false.
(B) If assertion is false but the reason is true.
(C) If both assertion and reason are true and the reason is a correct explanation of assertion
(D) If both assertion and reason are true but reason is not a correct explanation of assertion
NO2
Assertion :
r
i
S
.
J
.
PCl5
C= N
OH
OMe
O2N
C NH
OMe
OMe
Reason :
Migratory aptitude of
group is greater than migratory aptitude of
group during
NO2
cation rearrangements.
Q.23
Each of the compounds in Column A is subjected to further chlorination. Match the following for them.
Column-A
Column-B
(A) CHCl2 CH2 CH3
(P)
Optically active original compound
(B) CH2Cl CHCl CH3
(Q)
Only one trichloro product
(C) CH2Cl CH2 CH2Cl
(R)
Three trichloro product
(D) CH3 CCl2 CH3
(S)
Four trichloro product
Cl Cl
(E) CH3 C C CH3
CH3 CH3
Q.24
(T)
Atleast one of the trichloro product is optically active
(U)
Two trichloro products
Column-I and Column-II contains four entries each. Entries of column-I are to be matched with some entries
of column-II. One or more than one entries of column-I may have the matching with the same entries of
column-II and one entry of column-I may have one or more than one matching with entries of column-II.
Column-I
Column-II
(Reaction)
(Type of intermediate formed)
HO
(A) PhCHCl 2 (A)
(P)
Carbocation
(Q)
Carbanion
(R)
Free- radical
(S)
Carbene
Na
(B) R Br
dry ether
O
(i) Mg / H O
(C) CH C CH 2
3
3
(ii) H SO
2
CH3 OH
(D)
4,

48
Q.25
Column-I
Column-II
O
(A) Caprolactum formation take place in
HN
(P)
H2SO 4
N OH
(B) Beckmann rearrangement is
(Q)
OH
(C) Schmidt reaction is
(i) CHCl / HO
(R)
(ii) H
OH
r
i
S
.
J
.
Ph
(D) Reaction in which number of carbon increases
PCl
C= N
(S)
CH3
EXERCISE III
Q.1
(ii) Ph CH = CH2 + N2
Identify P1 to P8.
CH3 CH = CH CH2
CH3
CH2
D
HBr
CH3
CH3 CH = CH CH2 CH CH2
HBr
Q.5
P1 + P2 + P3 + P4
CH3 CH = CH CH2 CH CH2 CH CH3

D
P1 + P2 + P3 + P4 + P5 + P6 + P7 + P8
HBr
Compare the rate of decarboxylation in sodalime Q.6

process for the following.
(i) (a) HC C COOH (b) CH2 = CH COOH
(c) CH3 CH2 COOH
(ii) (a) CH2 CH2 COOH (b) FCH2 CH2 COOH
(c)
(a)
Formulate the reactions between but-1-ene

in presence of small amount of benzoyl
peroxide and (i) CCl4
(ii)
CBrCl3
Give your reasons.
(b) The dichlorocarbene reacts with phenol in
base where as it doesn't reacts with
benzene explain.
Give the product of the following reaction.
O
Mg
(i)
A
H2O
(ii)
CH = O
Mg
CH = O
(c) Cl CH2CH2 COOH

(iii) (a) CH3 CH COOH (b) CH3 CH COOH
H2O
(iii)
Cl
Mg
Me C Et
H2O
(iv)
Which compound is more stable explain.
Q.7
(a) CH3 C CH = N = N and CH3 CH = N =
Ph C Me
MeOCH Cl
BuLi
CHBr
3

?
t
BuOK
H SO
Br
H SO
2
4
(B) 2
(D) = ?
(C)
CCl 4
Give product and suggest mechanism for these

reactions.
(i) ? 2
Mg
H2O
2
D
Identify missing products in the given reaction

sequence.
Br2 / h
aq. KOH
(a) CH3 CH2 CH3
(A)
Q.4
CH3 CH COOH
H SO
2
C
CH3
Q.3
B. Find
CH2 CH2
out A & B.
(iii) Cl3C C OH + Na A
P1 + P2
NO2
Zn
Q.2
CO2Et ?
O
C Cl
(b)
NaN
Ag O
3
2

(P)
(Q)
H2O
NaNO 2
(R) (S)
HCl

49
Q.8
Find out the total number of products (including

stereo) in the given reaction:
OH
CH3
CH3
NBS,CCl
4

Products.
X CH2 CH2 XCH2 C H2 + H X
heat
CH3
XCH2 CH3 + X
conc .
+ H2O
H2SO 4
HCl
HBr
HI
67
25.1
+46
Q.10
Addition of small amount of (C2H5)4 Pb to a

mixture of methane and chlorine, starts the
Q.16
reaction at 140C instead of the usual minimum
250C. Why?
Q.12
1,2-Dimethylcyclohexene
Isopropylidenecyclopentane
(a) Write a reasonable and detailed mechanism

for the following transformation.
Q.11
C(CH3)2
2,2-Dimethylcyclohexanol
With the help of following data show HBr exhibits

Q.15
the peroxide effect.
1
1
H1/ kJ mol
H2/kJ mol
H X X + CH2 = CH2
CH3
Peroxide ,
Q.9
CH3
+ 12.6
50.2
117.1
OH
(b)
HO
OH
H / HOH
r
i
S
.
J
.
On chlorination, an equimolar mixture of ethane

and neopentane yields neopentyl chloride and
ethyl chloride in the ratio 2.3 : 1. How does the
reactivity of 1 hydrogen in neopentane compare
with that of a 1 hydrogen in ethane?
It required 0.7 g of a hydrocarbon (A) to react

completely with Br2(2.0 g) and form a non
resolvable product. On treatment of (A) with HBr it Q.17
yielded monobromo alkane (B). The same
compound (B) was obtained when (A) was treated
with HBr in presence of peroxide. Write down the
structure formula of (A) and (B) and explain the
reactions involved.
- Terpeniol
Geraniol
Assuming that cation stability governs the barrier

for protonation in HX additions, predict which
compound in each of the pairs in parts (a) and (b)
will be more rapidly hydrochlorinated in a polar
solvent.
(I)
(II)
(a)
CH2 = CH2
or
(b)
or
Choose the member of the following pairs of

unsaturated hydrocarbons that is more reactive
towards acid-catalysed hydration and predict the
regiochemistry of the alcohols formed from this
compound.
(a)
or
Q.13
Give product(s) in each of the following reactions.
Br / h
(a) CH3 CH CH2 CH2 CH3 2 (A)(major)
CH3
(C H CO) O
+ NBS 65 2 (B)
S
(b)
or
(i)
CH3
(b)
CH3
(c)
or
CH3
(ii)
Give product in the following reaction.

(i)
NaNO
2
CH3 C O Cl /
(d)C6H5CH2CH2CH3
(ii)
(i)
(c) CH3CH2CH=CH2+Me3COCl
(C) + (D) Q.18
Q.14
(ii)
(i)
NH2
(E)(major)
We saw that acid-catalyzed dehydration of 2,2dimethyl-cyclohexanol

afforded
1,2dimethylcyclohexene. To explain this product we
must write a mechanism for the reaction in which
a methyl shift transforms a secondary carbocation
to a tertiary one. Another product of the
dehydration of 2,2-dimethylcyclohexanol is
isopropylidenecyclopentane. Write a mechanism
to rationalize its formation.
(ii)
HCl
NH2
NaNO2
HCl
NH2
CH2NH2
(iii)
NaNO2
HCl
(v)
NaNO2
OH NH2
HCl
(iv)
NaNO2
HCl

50
Q.19
What are the products of the following reactions?

(B) CH3CH2CHBr
(a) PhCH = CHCH3 + HBr A

H3C
(b)
CH3
C=C
H3C
+ HI B
Peroxide
(c)
Q.5
CH3
+ HCl D
CH2CH3
Complete following reaction:

HCl
Br2
CCl4
(b)
CH2
CH3
CS2
Reaction of RCO NH2 with a mixture of Br2 and

KOH gives R NH2 as the main product. The
intermediates involved in this reaction are :
Q.8
[JEE 1992]
(A) R CO NHBr
(B) RNHBr
(C) R N = C = O
(D) R.CO.NBr2
Which one of the following has the smallest heat
Q.9
of hydrogenation per mole?
[JEE 1993]
(A) 1-Butene
(B) trans-2-Butene
(C) cis-2-Butene
(D) 1,3-Butadiene
In the following compounds :
OH
N
OH
The reaction of CH3CH=CH

HBr gives :
(A) CH3CHBrCH2
OD
The correct order of basicities of the following

compounds is:
[JEE 2001]
NH
CH3CH2NH2
NH2
(1)
(2)
(CH3)2NH
CH3CNH2
(3)
(4)
(B) 1 > 3 > 2 > 4

(D) 1 > 2 > 3 > 4
Q.10
Left to right sp , sp , sp, sp hybridization is

present in :
[JEE 2003]
(A) H2C = CH C N (B) H2C = C = CH CH3
(C) HC C C CH (D) HC C CH = CH2
Q.11
Maximum dipole moment will be of: [JEE 2003]

(A) CCl4
(B) CHCl3 (C) CH2Cl 2 (D) CH3Cl
OH with
[JEE 1998]
OH
Amongst the following, the most basic compound

is
:
[JEE 2000]
(A) C6H5NH2
(B) p-NO2C6H4NH2
(C) m-NO2C6H4NH2
(D) C6H5CH2NH2
(A) 2 > 1 > 3 > 4

(C) 3 > 1 > 2 > 4
NO2
(D) CD2 = C CD3
A solution of (+) 1-chloro-1-phenylethane in

toluene racemizes slowly in the presence of small
amount of SbCl5 due to formation of:
[JEE 1999]
(A) carbanion
(B) carbene
(C) free radical
(D) carbocation
OH
(I)
(II)
(III)
(IV)
The order of acidity is :
(A) III > IV > I > II
(B) I > IV > III > II
(C) II > I > III > IV
(D) IV > III > I > II
Q.4
(B) CH3 C CH3
CH3 C = CH2
CH3 C
[JEE 1996]
NO2
CH3
[JEE 1999]
The enol form of acetone, after Prolonged

treatment with D2O, gives:
[JEE 1999]
O
OD
(C) CH2 = C CH2D
EXERCISE IV (A)
OH
An aromatic molecule will:

(A) have 4n electrons
(B) have (4n +2) electrons
(C) be planar
(D) be cyclic
(A)
Total number of products obtained in this reaction

Q.7
is?
Q.3
Br
OH
Cl2
(c)
Q.2
(D) CH3CH2CHBr
r
i
S
.
J
.
Q.6
CH3
Q.1
Br
+ HBr
C
(d)
(a)
(C) CH3CHBrCH2
CH3
Q.20
OH
OH
COOH
Q.12
H
O 2N
M
OH
when X is made to react with 2 eq. of NaNH2 the

product formed will be :
[JEE 2003]

51
Q.18
OOC
OH
(A)
OOC
(B)
H
OH
O2N
M
OH
O 2N
M
OOC
(D)
CH3
OH
O2N
M
Ph MgBr +CH3 C OH
r
i
S
.
J
.
CH3
(A)
[JEE 2004]
(B) CH3 C OPh

CH3
COOH
x
Correct order of acidic strength is:

(A) x > y > z
(B) z > y > x
(C) y > z > x
(D) x > z > y
OH
CH3
(C)
(D) CH3 C Ph
Order of rate of reaction of following compound

with phenyl magnesium bromide is: [JEE 2004]
Ph C Ph
Me C H
O
(I)
(II)
(III)
(A) I > II > III

(C) III > I > II
Q.15
Q.19
CH3
NH3
H3N
z
M
O2N
M
Q.14
HOOC
OH
(C)
Q.13
For 1-methoxy-1,3- butadiene, which of the

following resonating structure is the least stable?
[JEE 2005]
(A)
H2 C CH CH CH O CH3
(B) H C CH CH CH
O CH3
2

(C)
H 2 C CH CH CH O CH3
(D) H C CH CH CH
O CH3
2
Me C Me
(B) II > III > I

(D) II > I > III
CH3
Q.20
When benzene sulfonic acid and p-nitrophenol

are treated with NaHCO3, the gases released
respectively are
[JEE 2006]
(A) SO2, NO2
(B) SO2, NO
(C) SO2, CO2
(D) CO2, CO2
Q.21
(I) 1,2-dihydroxy benzene

(II) 1,3-dihydroxy benzene
(III) 1,4-dihydroxy benzene
(IV) Hydroxy benzene
[JEE 2006]
The increasing order of boiling points of above
mentioned alcohols is
(A) I < II < III < IV
(B) I < II < IV < III
(C) IV < I < II < III
(D) IV < II < I < III
Q.22
CH3NH2 + CHCl3 + KOH Nitrogen containing

compound + KCl + H2O. Nitrogen containing
compound is
[JEE 2006]
(A) CH3 C N
(B) CH3 NH CH3
1-Bromo-3-chloro cyclobutane on reaction with 2equivalent of sodium in ether gives [JEE 2005]
Cl
Br
(A)
(B)
(C)
(D)
SO3H
CH3COONa(excess)
Q.16
(aq. solution)
Me
[JEE 2005]
(D) CH3N C
(C) CH3N C
SO2COOCH3
(A)
(B)
Me
SO3Na
(C)
Question No. 23 to 25 (3 questions)

Comprehension I
RCONH2 is converted into RNH2 by means of
Hofmann bromamide degradation.
COONa
+ CH3COOH
(D)
+ H2SO4
Cl
Cl
NH2
Me
Q.17
Me
Conversion of cyclohexanol into cyclohexene is

most effective in:
[JEE 2005]
(A) concentrated H3PO4 (B) concentrated HCl
(C) concentrated HCl/ZnCl 2
(D) concentrated HBr
Cl
(ii)
(i)
(iii)
OM
O
C
O
H2N
NBr
NHBr
Cl
Cl
Cl
H
(vi)
(v)
(iv)

52
In this reaction, RCONHBr is formed from which

this reaction has derived its name. Electron
donating group at phenyl activates the reaction.
Hofmann degradation reaction is an
Intramolecular reaction.
Q.28
The structure of the intermediate I is: [JEE 2007]
ONa
CH2Cl
CHCl2
(A)
(B)
CH3
Q.23
Q.24
Q.25
How can the conversion of (i) to (ii) be brought

about?
[JEE 2006]
(A) KBr
(B) KBr + CH3ONa
(C) KBr + KOH
(D) Br2 + KOH
15
CH2OH
2
CCl3
(C)
(D)
CH3
CH3
Q.29
Hyperconjugation involves overlap of the following

orbitals:
[JEE 2008]
(A) (B) p (C) p p (D)
r
i
S
.
J
.
The correct stability order for the following

species is:
[JEE 2008]
(I)
(ii)
(i)
ONa
ONa
What are the constituent amines formed when the

mixture of (i) and (ii) undergoes Hofmann
Q.30
bromamide degradation?
CONH2
CH3
Which is the rate determining step in Hofmann

bromamide degradation?
[JEE 2006]
(A) Formation of (i)
(B) Formation of (ii)
(C) Formation of (iii)
(D) Formation of (iv)
CONH2
ONa
(II)
NH2
NH2
NH2
NH2
NH2
(C)
(D)
15
NH2
NH2
15
NHD
Q.31
15
NH2
(III)
(IV)
(A) (II) > (IV) > (I) > (III) (B) (I) > (II) > (III) > (IV)
(C) (II) > (I) > (IV) > (III) (D) (I) > (III) > (II) > (IV)
15
(B)
15
15
(A)
In the following carbocation , H/CH3 that is most

likely to migrate to the positively charged carbon
is
[JEE 2009]
[JEE 2006]
HO
4 5
H3C C 3C C CH3
Paragraph for Question Nos. 26 to 28 (3 questions)

Riemer-Tiemann reaction introduces an aldehyde
group, on to the aromatic ring of phenol, ortho to
the hydroxyl group. This reaction involves
electrophilic aromatic substitution. This is a
general method for the synthesis of substituted
salicylaldehydes as depicted below.
ONa
OH
CHO
(I)
(Intermediate)
CH3
(I)
Q.26
Q.27
(B) H at C-4
(D) H at C-2
EXERCISE IV (B)
Q.1
OH
Complete the following, giving the structures of

the principal organic products: [JEE 1997]
(a)
CHO
Ph
+ KNH2
aq.HCl
CH3
(II)
CH3
(A) CH3 at C-4

(C) CH3 at C-2
Ph
(b)
CH3
(III)
Br
+ CHBr3 + t- BuOK
Q.2
Write the intermediate steps for each of the
Which one of the following reagents is used in the
following reaction.
[JEE 1998]
above reaction?
[JEE 2007]
H
O
3
(A) aq. NaOH + CH3Cl (B) aq. NaOH + CH2Cl2
(i) C6H5CH(OH) C CH
C6H5CH = CH CHO
(C) aq. NaOH + CHCl 3 (D) aq. NaOH + CCl 4
The electrophile in this reaction is [JEE 2007]
(A) : CHCl
(B) +CHCl2
(C) :CCl2
(D) CCl 3
(ii)
OH
CH3

53
Q.3
Out of anhydrous AlCl3 and hydrous AlCl3 which

is more soluble in diethyl ether?
Explain with reason.
[JEE 2003]
Q.4
Match Ka values with suitable acid: [JEE 2003]
(i)
Ka
5
3.3 10
(ii)
4.2 10
(iii)
6.3 10
(iv)
6.4 10
(v)
Acid
(a)
NH3
NH3
COOH
COOH
MeO
(e)
OH
Which of the following is more acidic and why?
[JEE 2004]
COOH
Cl
(d)
Give resonating structures of the following

compound.
[JEE 2003]
Me
(c)
30.6 10
Q.6
COOH
(b)
Q.5
r
i
S
.
J
.
F
COOH
O2N
ANSWER KEY
EXERCISE-1
Q.No.
Ans.
Q.No.
Ans.
Q.No.
Ans.
Q.No.
Ans.
1
B
16
C
31
B
46
C
2
B
17
B
32
C
47
D
3
C
18
C
33
D
48
B
4
C
19
A
34
A
49
C
5
D
20
A
35
C
50
A
6
B
21
D
36
A
7
C
22
C
37
C
8
B
23
D
38
A
9
D
24
C
39
B
10
D
25
B
40
C
11
A
26
D
41
B
12
D
27
D
42
C
13
C
28
B
43
D
14
C
29
C
44
B
15
B
30
A
45
A
EXERCISE-II
Q.No.
Ans.
Q.No.
Ans.
Q.No.
Ans.
Q.No.
Ans.
1
8
A,B,C
19
A,C,D
24
Q.1
A
Q,R
9
A,B
20
B,C
A
Q,S
B
P,S
10
A,B,C
21
A,C
B
Q,R
C
Q
11
A,B,D
22
B
C
P,R
N
H
P1 = CH3C CH2 C CH2 C CH3

Br

Br
D
P,S
12
A,B,D
23
2
A,B,C
13
A,B,D
A
S,T
D
P
25
3
B,D
14
A,B,D
B
P,S,T
A
P,Q
4
B,C,D
15
A,B,D
C
U
B
Q,S
5
A,B,D
16
A,B,C
D
Q
C
P
6
B,D
17
A,B,D
E
T,U
D
R
7
B,C
18
C,D
EXERCISE-III
Br

H
Br
D
D
T
H

H

54
Br
Br
Q.2
P8 = CH3 C CH2 C CH2 C CH3

H

Br
Br
(i) a > b > c; (ii) a > b > c ; (iii) b > a > c Q.3
(a) Due to Resonance
Br
Q.4
(i)
OMe (ii)
&
Br
(iii) A : CCl2
B:
Cl
Q.5
(a) Free radical mechanism
(a)
CH3 CH2 CH3
(b) Due to more electron density
Br2/h
Br2
CCl4
CH2 CH CH3
aq.KOH
CH3 CH CH3
(B)
CH2 = CH CH3
(C)
Br
(D)
C Cl
C N3
(b)
OH
CH3 CH CH3
(A)
Br
r
i
S
.
J
.
Cl
Br
Q.7
COOEt
Ph
NaN3
OH
N=C=O
Ag2O
NH2
NaNO2
H 2O
+HCl
CH3
CH2 Br
CH2
Br
Q.8
and its enantiomer,
CH3
and its enantiomer,
Br
CH3
Br
and its enantiomer,
Q.11
1.15 times more reaction
Q.13
(a) A :
Br
CH3
Br
Q.12 A =
Br
CH3 C CH2CH2CH3
(c) C: CH3 CH CH = CH2

Cl
CH3
D: CH3 CH = CHCH2Cl
CH2Br
(b)B :
S
(d) E:
Ph CH Et
Cl

55
OH
Q.15
(b)
HOH/H
OH
Q.16
(a) II, (b) I
Q.19
(a)
Q.17 (a) II, (b) I, (c) II

(b) Me2C(I) Et,
Ph CH Et
(c)
Br
Br
CH3
Q.20
(a)
Cl
r
i
S
.
J
.
CH3
CH3
CH3
Br
Br
(b)
(diastereoisomers)
+
Br
Br
Me
Me
Me
Et
Et
(diastereoisomers)
+
Cl
(c) H
H
Cl
(d)
Me
H
H
Cl + Cl
Cl Cl
(Enantiomers)
Et
EXERCISE IV(A)
Q.No.
Ans.
Q.No.
Ans.
Q.No.
Ans.
1
C
16
C
31
D
2
D
17
A
3
D
18
C
4
B
19
A
5
B,C,D
20
D
N
Br
Q.1
7
D
22
D
8
D
23
D
9
B
24
D
10
A
25
B
11
D
26
C
12
C
27
C
13
D
28
B
14
B
29
B
15
C
30
D
EXERCISE IV(B)
(A) PhC CPh, (B)
C6H5CH C CH
Q.2
6
D
21
C
OH
C6H5CH C CH
H2O
C6H5CH C CH
+
OH2
OH2
C6H5CH =C = CH
H2O
C6H5CH =C = CH
C6H5CH =C = CH
+
tautomerism
C6H5CH =CH CHO
OH2

56
+
H
(ii)
OH
OH
H +
+
O|
CH3
CH3
Q.3
Anhydrous AlCl 3 is more stable then hydrous AlCl3 because it is having vacant 3p orbital of Al which can
accept lone pair of electrons from oxygen of diethylether.
Q.4
(i)-(d), (ii)- (b), (iii) (a), (iv) (c), (v)-(e) Q.5
r
i
S
.
J
.
OH
NH3
Q.6
is more acidic as overall effect of F is electron withdrawing so loss of portion is easier from this
compound.

57

Reaction Intermediate

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Reaction Intermediate

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IIT-JEE ChEmistry by N.J.

---------------------------------------------------------------------------------------------------ETOOS Academy Pvt. Ltd.

IIT-JEE ChEmistry by N.J. sir

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IIT-JEE ChEmistry by N.J. sir

CH3 CH2 CH2 O

3, 3Dimethylbutan2ol loses a molecule of

CH3 CH CH3 + :O:

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IIT-JEE ChEmistry by N.J. sir

NaNO2 + HCl HON=O + NaCl

Diazotization of primary amine:

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IIT-JEE ChEmistry by N.J. sir

+ CH3 CCH2CH3 CH3 CCH2CH3

---------------------------------------------------------------------------------------------------ETOOS Academy Pvt. Ltd.

Diels Alder Reaction:

The reaction of propene with HOCl proceeds via

(C) CH3 CH2 CH

The number of stereoisomers

Write down the structures of the stereoismers

(D) CH2 CH2 CH2

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IIT-JEE ChEmistry by N.J. sir

Fill in the blanks:

Intermediate Carbocation rearrangedCarbocation

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Q.5 CH3 CH2 + CH3 CH2

A & C are Idenitcal / Isomers / Positon Isomers.

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IIT-JEE ChEmistry by N.J. sir

Which of following carbocation will undergo

(A) , Major product (A) is

(i) CH2 O CH2 CH2 CH2

(n) CH2 CH2 CH2

(t) (CH3)3 C CHCH3

(s) (CH3)2 CH CHCH3

(A) an heating isomerizes to (B). What is the

Sum of -hydrogen (A + B + C) is.

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In which of following reaction rearrangement take

(D) CH3 CH CH3

In which of following reaction resonance stabilized

Sum of -hydrogen in major product of the

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IIT-JEE ChEmistry by N.J. sir

Compare rate of dehydration (acid-catalyzed)

Predict the major product

CH2 CH CH2 CH2 CH2

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Predict Major Product

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IIT-JEE ChEmistry by N.J. sir

Identify major products:

What will be major product obtained from

CH3 CH CH2 CH = CH2

Find total product in following reaction ? (including

(y) (products) (Markonikoff products)

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IIT-JEE ChEmistry by N.J. sir

How will prepare following compound using alkene