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REACTION MECHANISM 1 ----------------------------------------------------------------------------------------------------

REACTION

MECHANISM

1

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IIT-JEE ChEmistry by N.J. sir

ORGANIC chemistry

DPP NO-01

Time: 15 minutes

Q.1

(a)

(b)

(c)

(d)

(e)

(f)

CH 3 —CH 2 —CH 2   
CH 3 —CH 2 —CH 2 



CH 3

CH —CH —CH —C—CH

3

2

2

CH

3

 CH 3 CH —CH —CH —C—CH 3 2 2 CH 3 2   

2



 CH 3 CH —CH —CH —C—CH 3 2 2 CH 3 2   (g) Ph—CH

 —CH —C—CH 3 2 2 CH 3 2    (g) Ph—CH 2 —CH 2


(g) Ph—CH 2 —CH 2

   (g) Ph—CH 2 —CH 2  ( h ) CH 3 CH 3



(h)

CH

3

CH 3 —CH—CH —CH

2

2  ( h ) CH 3 CH 3 —CH—CH —CH 2 2  (i) (

2



(i)

(j)

(k)

(l)

(m)

(n)

Ph

Me

Ph—C— CH—CH 2 —CH 2

j ) (k) (l) (m) (n) Ph Me Ph—C— CH—CH 2 —CH 2 D  CH

D



CH –O 3 
CH –O
3


Ph

C—CH —CH —CH

2

2

Ph

CH –O 3  Ph C—CH —CH —CH 2 2 Ph 2  CH —CH—CH —OH

2



CH —CH—CH —OH

3

2



OH

 CH 3 Me CH 3 —C— C—et OH

CH 3 Me
CH 3 —C— C—et
OH

(o)

(p)

(q)

(r)

(s)

(t)

(u)

(v)

CH 3 CH — C — C = O: 3 :
CH 3
CH — C — C = O:
3
:

H

CH—OH  CH 2   CH 2   `  
CH—OH

CH 2
 
CH
2


`
 

 CH 2   `     _ _ OH (w)  OH

 2   `    _ _ OH (w)  OH (x)  `

_

_

OH (w)  OH (x)  `
OH
(w)

OH
(x)

`

2

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ETOOS Academy Pvt. Ltd.

F-106, Road No. 2, Indraprastha Industrial Area, End of Evergreen Motors (Mahindra Showroom), BSNL Office Lane, Jhalawar Road, Kota, Rajasthan (324005)

IIT-JEE ChEmistry by N.J. sir

ORGANIC chemistry

DPP NO-02

Time: 15 minutes

Dehydration of Alcohol Q.1 CH 3 —CH 2 —CH 2 —OH CH 3 —CH=CH 2
Dehydration of Alcohol
Q.1 CH 3 —CH 2 —CH 2 —OH
CH 3 —CH=CH 2
 Conc.H 170  C SO
2
4
Mechanism:–
(1)
CH 3 — CH 2 — CH 2 — O   — H
+ H +
CH 3 — CH 2 — CH 2 —
rds
CH—CH—CH
CH 3 — CH 2 — CH 2  + 
3
3
H
+
(2)
+
CH —CH=CH + H O
CH — CH — CH
:O:
3
2
3
3
3
H

Energy profile diagram:—

E Reaction H  /  Q.1  _ OH H  /  Q.2
E
Reaction
H
 / 
Q.1

_
OH
H
 / 
Q.2


Q.3

Q.4

Q.5

Q.6

OH

H  /   OH H  /  OH  _ Conc.H SO
H
 / 

OH
H
 / 
OH

_
Conc.H SO

2
4
OH
Conc.H SO
OH

2
4

OH

H  Q.7   OH Conc.H SO Q.8  2 4  H 
H
Q.7

OH
Conc.H SO
Q.8

2
4
H
 / 
Q.9
OH

Q.10
OH
H
 / 


Q.11

Q.10 OH H  /   Q.11 OH H  /    

OH

H

/

Q.8 3, 3–Dimethyl–butan–2–ol 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:– C = C  ENu C — C
Electrophilic addition:–
C = C
 ENu C — C

E

Nu

Mechanism:–

C = C + E
C = C
+ E



—C — C— E  Nu Nu :
—C — C—
E
Nu
Nu
:

—C — C—

E

Q.1

Compare rate of electrophilic addition on alkenes:–

(a)

(i) (ii)
(i)
(ii)

(b) CH = CH 2 (b) CH = CH 2

NO 2

(i)

CH = CH

alkenes:– (a) (i) (ii) (b) CH = CH 2 NO 2 (i) CH = CH CN

CN

(ii)

(iii) (iv) CH = CH 2 2
(iii)
(iv)
CH = CH 2
2

(iii)

CH = CH 2 CH = CH 2 O – Me NH 2 (iv) (v)
CH = CH
2 CH = CH
2
O – Me
NH
2
(iv)
(v)

COOH (c) COOH

(i)

(ii) (iii) (iv) (v)
(ii)
(iii)
(iv)
(v)

(d) Ph — CH = CH 2 (i)

PH — CH = CH — Ph (ii)

3

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ETOOS Academy Pvt. Ltd.

F-106, Road No. 2, Indraprastha Industrial Area, End of Evergreen Motors (Mahindra Showroom), BSNL Office Lane, Jhalawar Road, Kota, Rajasthan (324005)

Q.1

Q.2

CH 2 = CH 2

HI



KBr

CH 2 = CH 2

Q.3  KBr HI Q.4  KBr HI C = CH 2 HI Q.5 
Q.3
 KBr HI
Q.4
 KBr HI
C = CH 2
HI
Q.5

_ _
KF
HI
Q.6

Q.7
HCl

O
HI
Q.8
_

HI
Q.9
(Ph) CH—CH—CH=CH
2 
2

Q.10

Q.11

Q.12

Q.13

Q.14

Me

HBr2  2 Q . 1 0 Q.11 Q.12 Q.13 Q.14 Me C = CH—Ph 

C = CH—Ph



HCl _ _   HBr CH 2 = CH — Cl  HCl
HCl
_
_

 HBr
CH 2 = CH — Cl 
HCl

CH CH HCl(2eq.)

Q.15

Q.16

Q.17

Q.18

Q.19

Q.20

Q.21

Q.22

Q.23

Q.24

Q.25

Q.26

Q.27

Q.28

 HCl(2eq.) CH 3 — C  CH  HCl  dil.H SO 2 4
 HCl(2eq.)
CH 3 — C 
CH
 HCl
 dil.H SO
2
4
H
 /H O

2
 H /R–OH
H
 /H O

2
_

Me

HCl _ D  H CH = CH 2 D  /D O  2
HCl
_
D 
H
CH = CH
2
D
 /D O

2
O
+
H
H
HBr

_
CH 
C — CH
2 — CH = CH
HCl
2 
CH  C — CH = CH
HCl
2 
H
HO—CH —CH —CH —CH = CH
2
2
2
2 
MeOH

OH

CH = CH—CH—CH=CH

2

2

 H /MeOH

H  Q.29  O
H 
Q.29

O

H

4

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ETOOS Academy Pvt. Ltd.

F-106, Road No. 2, Indraprastha Industrial Area, End of Evergreen Motors (Mahindra Showroom), BSNL Office Lane, Jhalawar Road, Kota, Rajasthan (324005)

:

:

:
:

IIT-JEE ChEmistry by N.J. sir

ORGANIC chemistry

DPP NO-03

Time: 15 minutes

Q.1 OH OH O H H H  H  Q.3   CH 3
Q.1
OH
OH
O
H
H
H
H
Q.3
 
CH 3 —CH—CH—CH 3
 
CH 3 —CH 2 —C—CH 3
OH
OH
OH
OH
Mechanism:–
CH 3
CH 3
(1)
H
+
Q.4
 
CH —CH—CH—CH
+ H
+ 
H O + CH —CH—CH—CH
3
3
2
3
3
O–H O–H
O–H
OH
OH
H
Q.5

CHO
C — C —
3
H
H
+
OH
OH
s 
CH — CH —C—CH

CH — CH —C—CH
3
2
3
3
2
3
H
O—H
Q.6

O—H
+
CH
CH
3
OH
OH
3
H
H
Q.1

Et — C — C —Et
Q.7
:
:

OH
OH
Ph
Diazotization of primary amine:–
H
Q.2
Ph— C — CH

2

NaNO
:
2
OH
OH
R — NH

R — N
N:

R
N
2
HCl
2

Mechanism:–

(1)

(2)

NaNO 2 + HCl  H—O—N=O + NaCl

H — O — N = O + H

H O +

2

H R—N: + N = O :
H
R—N: +
N = O
:

H



N=O + H :
N=O
+
H
:
R—N — N = O : H
R—N — N = O
:
H

(3)



H

N=O + H : R—N — N = O : H (3)  H R—N—N =

R—N—N = O—H

:: H R—N= N—O—H
::
H
R—N= N—O—H

N

2

R

R — N N:

R—N = N

R    R — N N:   R—N = N   H :
 
  H : H

H

:

  H : H

H

+

O

 R—N = N—O:

H H

H

H H

H

5

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ETOOS Academy Pvt. Ltd.

F-106, Road No. 2, Indraprastha Industrial Area, End of Evergreen Motors (Mahindra Showroom), BSNL Office Lane, Jhalawar Road, Kota, Rajasthan (324005)

Demjanov Reaction:–

OH

NH 2

CH — CH—CH—CH

3

3

 NaNO HCl

2

O

2 CH — CH—CH—CH 3 3  NaNO HCl 2 O CH — C—CH —CH 3

CH — C—CH —CH

3

2

3

Mechanism:–

(1)

OH

NH 2

CH — CH—CH—CH

3

3

 NaNO HCl

2

OH

2 CH — CH—CH—CH 3 3  NaNO HCl 2 OH CH — CH—CH—CH + N

CH — CH—CH—CH + N

3

3

NaNO HCl 2 OH CH — CH—CH—CH + N 3 3 H + Q.1 Q.2 Q.3

H +

Q.1

Q.2

Q.3

O OH 3  CH — C—CH —CH CH — C—CH —CH 3 2 3
O
OH
3 
CH — C—CH —CH
CH — C—CH —CH
3
2
3
2
OH
NH
2
NaNO

2
CH — CH —
—OCH
3 HCl
NH
2 NaNO

2
HCl
OH
NH
2 OH
NaNO

2
HCl

3

2

Q.4

Q.5

Q.6

Q.7

Q.8

IIT-JEE ChEmistry by N.J. sir

OH NH 2 CH — CH —CH— 3  SbCl  5 Cl O—H OH
OH
NH 2
CH — CH —CH—
3
 SbCl 
5
Cl
O—H
OH
Br
 AlBr 
3
AgI

_

I O—H

NaNO HCl

2

OH I
OH
I

aq.AgNO

3



ORGANIC chemistry

DPP NO-04

Time: 15 minutes

Non Classical Carbocation:–

DPP NO-04 Time: 15 minutes Non Classical Carbocation:– E—Nu C = C  Nu —C —

E—NuDPP NO-04 Time: 15 minutes Non Classical Carbocation:– C = C  Nu —C — C—

C = C NO-04 Time: 15 minutes Non Classical Carbocation:– E—Nu  Nu —C — C— E Mechanism:– (1)

Time: 15 minutes Non Classical Carbocation:– E—Nu C = C  Nu —C — C— E



Nu

—C — C—

E

Mechanism:– (1)  C = C —C — C— + Nu E Nu : Nu
Mechanism:–
(1)

C = C
—C — C—
+
Nu
E
Nu
:
Nu
—C — C—
E
 Br
2
Q.1
CH 2 = CH 2
Q.2
CH 2 = CH 2
Br 2
O
H
H
Br
Q.3

2
CCl
4

Q.4

Q.5

Q.6

Q.7

Q.8

Q.9

Q.10

Q.11

Br  2 CCl 4 ICl CH —  CH = CH _ 3 2
Br

2
CCl
4
ICl
CH
— 
CH = CH
_
3
2
HOCl
CH
— 
CH = CH
3
2
Cl

2
CCl
4
Br

2
CCl
4
Br
/H O

2
2
Br

2
H O
2
2
4
 Br (1eq.) /CCl

6

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ETOOS Academy Pvt. Ltd.

F-106, Road No. 2, Indraprastha Industrial Area, End of Evergreen Motors (Mahindra Showroom), BSNL Office Lane, Jhalawar Road, Kota, Rajasthan (324005)

Q.12

Q.13

Q.14

H

N  Br (1eq.) (CCl ) 2 4 CH 3 — CH = CH 2
N
 Br (1eq.) (CCl )
2
4
CH 3 — CH = CH 2
 HCl
CH Cl / AlCl
3
3
CH Cl
3
CH = CH 2  HCl CH Cl / AlCl 3 3 CH Cl 3 H
H H–O
H H–O

CH 3

HCl Q.15 CH 3 O— 
HCl
Q.15
CH
3 O—


Q.13

Ans.

Q.18

Ans.

Q.23

Ans.

Q.26

Ans.

Q.5

Ans.

The reaction of propene with HOCl proceeds via

the addition of

(A)

(B)

(C) OH in first step

[IIT '2001]

H + in first step Cl + in first step

(D)

Cl + and OH

in single step

B

OH

(D) Cl + and OH – in single step B OH H  x Br 

H

x Br



H O

2

 2

(C) 4

5 compounds of

[IIT '2003]

(D) 5

(mixture)

Br 2

molecular formula C H

4

(B) 3

8

Number of compounds in X will be :

(A) 2

B

CH 3 – CH = CH 2 + NOCl P

Identify the adduct.

(A) CH 3 – CH – CH 2

[IIT '2006]

(B) CH 3 – CH – CH 2

Cl

(C) CH 3 – CH 2

NO

NO

– CH

NO

Cl

(D) CH 2 – CH 2 – CH 2

Cl

NO

Cl

A

The number of stereoisomers obtained by

bromination of trans-2-butene is

(A) 1

A

[IIT '2007]

(D) 4

(B) 2

(C) 3

Write down the structures of the stereoismers formed when cis-2-butene is reacted with bromine. [IIT '1995]

H

Br

Me

is reacted with bromine. [IIT '1995] H Br Me Me Br H + Me Br H

Me

Br

H

+

Me

Br H H Br
Br
H
H
Br

Me

Diel’s Alder Reaction:–

Q.1

Q.2

Q.3

Q.4

Q.5

Q.6

Q.7

+ | |   COOH +  COOH COOH +  HOOC + 
+ |
|


COOH
+

COOH
COOH
+

HOOC
+

NO
2

+
+

+ +
+
+

NO 2  + +  + +  Q.8 + Q.9 + O Q.10 +

+ +  + +  Q.8 + Q.9 + O Q.10 + O Q.11 Q.12

Q.8 + Q.9 + O Q.10 + O
Q.8
+
Q.9
+
O
Q.10
+
O

Q.11

Q.12

+ + O
+
+
O

O

Q.8 + Q.9 + O Q.10 + O Q.11 Q.12 + + O O  

Q.9 + O Q.10 + O Q.11 Q.12 + + O O    






   7

7

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IIT-JEE ChEmistry by N.J. sir

ORGANIC chemistry

DPP NO- 05

Time: 15 minutes

Fill in the blanks:– CH 3 OH Q.1 OH H
Fill in the blanks:–
CH 3
OH
Q.1
OH
H

O

 H   Mechanism :– CH 3 O OH (i) + H + H
H

Mechanism :–
CH 3
O
OH
(i)
+ H + H
H
OH
H



Intermediatecarbocation

(ii) 

Rearrargemet



Intermediatecarbocation

Rearrangedcarbocation

O

(iii)   H + + Rearrangedcarbocation   [H ] (iv) = - -
(iii) 
 H
+ +
Rearrangedcarbocation
 [H ]
(iv)
= -
- - -
- -
- -
- - -
- -
- -
 t
(v) Name of Reaction is - -
- -
- -
- -
- -
- - -
- - -
OH
OH
H
Q.2
CH — O
C
C
CH 3
 Product
3
H

Mechanism : –

OH OH CH — O C C CH + H   3 3 IntermediateCarbocation
OH
OH
CH — O
C
C
CH
+ H
 
3
3
IntermediateCarbocation

H

IntermediateCarbocation
rearrangedCarbocation

(i)

(ii)



RearrangedCarbocation





 H

+

Pr oduct



NH 2 OH NaNO |HCl. Q.3  2 PH C C CH Pr oduct 3
NH
2 OH
NaNO |HCl.
Q.3

2
PH
C
C
CH
Pr oduct
3

H
H
Mechanism : –
NH
2 OH
NaNO |HCl.
(i) PH
 - - - -
2
- - -
- -
- -
- -
C
C
CH 3
H
H
Rearrangement
- -
None of Reaction - - - - - - - - - - - - - -
H + +
- -
- -
- -
- - -

- - -
- -
- - -
- -
- -

8

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Q.4

CH

CH 3 CH 3 C° + CH 3 C° 3
CH 3
CH 3
+
CH 3
3



          Q.5 (Major Pr oduct)

CH 3 CH 3 C + C Q.6   Q.7 (explain) Mechanism : –
CH 3
CH 3
C
+
C
Q.6

 Q.7
(explain)
Mechanism : –

CH 3 — C ° H 2 + CH 3 — C°H 2 

 (Major Pr oduct)

Ph

H H C C CH 3 CH 3
H
H
C
C
CH 3
CH 3
O + CH = CH 2  H / Ph H
O
+
CH = CH 2  H / Ph
H

(i)

H H Ph C C CH = CH 2 CH 3 CH 3
H
H
Ph
C
C
CH = CH 2
CH 3
CH 3

+ H 

Pr oduct



Nucleophile



Intermediate



3



(Intermediate )

1

(Rearrangement) 3  (Intermediate ) 1  (Intermediate ) 2  Q.8 A



(Intermediate )

2



Q.8

A
A

HCl | CCl

4
4

Ph—CH= CH

HBr

CCl 4
CCl
4
B
B
D
D
D 2
2
2

HCl

R–O–O–R/CCl

4

HBr

(R–O–O–R)/CCl

C
C

4

 

Q.9

CH

CH 3 3 C
CH
3
3 C

H

CH

2

CH

Br /h

3 

2

2

A
A

aq.KOH



CH

CH 3 3 C
CH
3
3 C

OH

CH

2

CH

Q.10

Conc. H 2 SO 4 HBr(R–O–O–R) C  B CCl 4 A & C are
Conc. H
2 SO
4
HBr(R–O–O–R)
C

B
CCl
4
A
& C
are
Idenitcal / Isomers / Positon Isomers.
   
Ph
O
NaOH

Ph
C
C
OH
electrolysis

Ph

Anode (I) Ph O (ii) Ph C C
Anode
(I)
Ph
O
(ii) Ph
C
C

Ph

Ph O e — + Ph C C O° Ph O° CO 2 + 
Ph
O
e — +
Ph
C
C
Ph
O° CO 2 +

Intermediate

(iii) Intermediate

- - - - - - - - - - - -



(i)

Cathode

2H 2 O + 2e

3

9

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IIT-JEE ChEmistry by N.J. sir

ORGANIC chemistry

DPP NO- 06

Time: 15 minutes

1.

2.

Which

rearrangement?

of

following

carbocation

will undergo (d) + +
will
undergo
(d)
+
+
O
O
+ + CH 2 CH 2 (b) (c) + + + + (f) (g)
+
+
CH 2
CH 2
(b)
(c)
+
+
+
+ (f)
(g)
(d) + + O + + CH 2 CH 2 (b) (c) + + + +

(h)

(a)

(e)

Ph

(i)

(j)

+ CH — O — CH — CH — CH 2 2 2 2 +
+
CH — O — CH
— CH — CH
2
2
2
2
+
+

CH (i) (j) + CH — O — CH — CH — CH 2 2 2 2

(l)

+ +
+
+

(p)

Ph

CH

+
+

(k)

(m)

2 — C = O

+ CH — CH — CH (n) 2 (o) 2 2 CH — CH —
+
CH — CH — CH
(n)
2 (o)
2
2
CH
— CH — O
3
2

(q)

— CH — CH (n) 2 (o) 2 2 CH — CH — O 3 2
+ CH
+
CH
— CH (n) 2 (o) 2 2 CH — CH — O 3 2 (q) +

(r) CH 3 CH 2 CH 2 +

(s) (CH 3 ) 2 CH

CHCH

3

(t) (CH 3 ) 3 C

CHCH

3

) 2 CH  CHCH 3 (t) (CH 3 ) 3 C  CHCH 3 CH

CH —OH

2

(u) (CH 3 CH 2 ) 3 CCH 2

H



(A)

+

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

structure of (B). CH 3 (A) (B)
structure of (B).
CH
3
(A)
(B)
(C) (D)
(C)
(D)
OH
OH
Ph — CH — Ph CH — CH — OH 2 2 H  3.
Ph — CH — Ph
CH — CH — OH
2
2
H
3.


4.

5.

(A) , Major product (A) is

(major)

(A)

(B)

(C)

(D)

Ph — C — Ph

CH — CH 2 3 Ph — CH — Ph CH — CH 3
CH — CH
2
3
Ph — CH — Ph
CH — CH
3
Ph — CH — Ph CH — CH 2
Ph — CH — Ph
CH — CH
2
Ph Ph — C — OH CH — CH 2 3
Ph
Ph — C — OH
CH — CH
2
3

OH

H  Reaction-1  (A)  (major) H  Reaction-2  (A)  (major) OH
H
Reaction-1

(A)
(major)
H
Reaction-2

(A)
(major)
OH
H
Reaction-3

(A)
OH
(major)
Sum of -hydrogen (A + B + C) is.
H
(A)

(x)

OH

10

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F-106, Road No. 2, Indraprastha Industrial Area, End of Evergreen Motors (Mahindra Showroom), BSNL Office Lane, Jhalawar Road, Kota, Rajasthan (324005)

(B)

(C)

(D)

H    OH OH H   
H

OH
OH
H


OH

(y)

H



(p)

(z)

Total

number

of

products

obtained

in

above

reactions

including

minor

products

is

(include

stereoisomer) x y z p
stereoisomer)
x
y
z
p

6. In which of following reaction rearrangement take

place with change is carbon skeleton.

7.

(A)

(C)

(D)

CH 3 + (B) CH CH — C — CH 3 2 CH 3 +
CH
3
+
(B) CH
CH — C — CH
3
2
CH
3
+
CH — CH — CH — CH
3
2
2
CH
3
CH
3 — CH
 — CH
3

3

— CH 2 CH 2

Sum

reaction.

of

-hydrogen in major product of the

Reaction-1

OH

of  -hydrogen in major product of the Reaction-1 OH H    (A) OH

H



(A)

OH H  Reaction-2  (B)  Reaction-3 OH H    H 
OH
H
Reaction-2

(B)
Reaction-3
OH
H

H
Reaction-4
OH

(D)
Sum of -hydrogen is
A + B + C + D =

(C)

8. In which of following reaction resonance stabilized

product will form.

CH —OH 2 (A) OH (B) CH (C) OH (D) All
CH —OH
2
(A)
OH
(B)
CH
(C)
OH
(D) All

H



H



3 H



11

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IIT-JEE ChEmistry by N.J. sir

ORGANIC chemistry

DPP NO- 07

Time: 15 minutes

Q.1

Q.2

Q.3

Compare rate of dehydration (acid-catalyzed)

OH

Q.2 Q.3 Compare rate of dehydration (acid-catalyzed) O H OH (a) (b) (c) (e) OH OH
Q.2 Q.3 Compare rate of dehydration (acid-catalyzed) O H OH (a) (b) (c) (e) OH OH

OH

(a)

(b)

(c)

(e)

OH OH OH OH (d) OH OH
OH
OH
OH
OH
(d)
OH
OH

OH

(a) (b) (c) (e) OH OH OH OH (d) OH OH OH the OH major product

the

OH major product
OH
major
product

of

acid-catalyzed

Predict

dehydration of alcohols

(A) 2-pentanol (B) 1-methyl cyclopentanol (C) 2-methyl cyclohexanol (D) 2, 2-dimethyl-1-propanol Identify-Product
(A)
2-pentanol
(B)
1-methyl cyclopentanol
(C)
2-methyl cyclohexanol
(D)
2, 2-dimethyl-1-propanol
Identify-Product
H SO
(a)

2
4
OH
CH
3 CH
3
H
SO
(b)

2
4
CH —CH —C — CH—CH
3
2
3 
OH
— CH — OH
2
H PO
(c)

3
4
OH
H
PO
(d)

3
4
— CH — CH — CH
2
3

(e)

(f)

(g)

OH  H   CH 3  H  CH —CH —CH — C
OH
H

CH 3
H

CH —CH —CH — C —CH
3
2
3 
OH
CH 3
OH
H


Q.4

(h)

(i)

(j)

(k)

(l)

(m)

(n)

OH

 H   Q.4 (h) (i) (j) (k) (l) (m) (n) OH  A +

 A + B

H

 H  A + B H H  CH 3 OH CH 3 
H
 A + B
H
H
CH 3
OH
CH 3
H
 A + B
OH
OH
KHSO

4
170C

OH

H SO  2 4  OH H SO  2 4  CH 3
H
SO

2
4
OH
H SO

2
4
CH
3

OH

2 4  OH H SO  2 4  CH 3 OH OH  

OH



H SO

2

4

 H (o)   CD 3 OH  H (p)   OH CH
H
(o)

CD
3
OH
H
(p)

OH
CH
3
D
D
H
(q) D
D

Cl  H (r)   OH H PO (s)  3 4  OH
Cl
H
(r)

OH
H PO
(s)

3
4
OH
Write – Mechanism
H
(a)
OH

H SO
(b)

2
4

(c)

CH

2

OH

— CH — CH — CH — CH

2

2

2

H



OH

OH

18

O
O

CH 3

+ H 2

18

O

12

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Q.5

Ans.1

Ans.2

Ans.3

Predict Major Product

HCl (a)  CH 2 HCl (b)  HCl (c)  HCl (d) 2-methyl propene
HCl
(a)

CH 2
HCl
(b)

HCl
(c)

HCl
(d) 2-methyl propene

Hl
(e) 1-methyl cyclohexene

OH
(a)
OH
OH
OH
(b)
OH
OH
(c)
(d)
OH
OH
OH
(e)
OH
C
(A)
(B)
(C)
(D)
C — C = C — C
(a)
(b)
(c)
(d)
(e)
(f)
(g)
(h)
+

Ans.5

(i)

(j)

Me Me
Me
Me

(k)

(c) (d) (e) (f) (g) (h) + Ans.5 (i) (j) Me Me (k) Cl Cl (m)
(c) (d) (e) (f) (g) (h) + Ans.5 (i) (j) Me Me (k) Cl Cl (m)

Cl

(c) (d) (e) (f) (g) (h) + Ans.5 (i) (j) Me Me (k) Cl Cl (m)

Cl

(m)(d) (e) (f) (g) (h) + Ans.5 (i) (j) Me Me (k) Cl Cl (o) CD

(o) CD 3 D D (q) D
(o)
CD
3
D
D
(q) D
+ Ans.5 (i) (j) Me Me (k) Cl Cl (m) (o) CD 3 D D (q)

Cl

(i) (j) Me Me (k) Cl Cl (m) (o) CD 3 D D (q) D Cl
Cl I
Cl
I

(s)

(b)

(d)

(l)

(n)

(p)

(r)

(a)

(c)

(e)

13

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IIT-JEE ChEmistry by N.J. sir

ORGANIC chemistry

DPP NO- 08

Time: 15 minutes

Q.1

Q.2

Identify major products: H H  H O (d)  3 CH 3 C =
Identify major products:
H
H
H O
(d)

3
CH 3
C = C
HgSO
(a)

4
Ph
Ph
CH
3 — C — C
CH
H SO
2
4
HBr
CH 3
(e)

CCl
4
HgSO
(b)
CH 3 — C  CH

4
H
2 SO
4
(f)
D–Cl (x)
+
D O
3
HgSO
(y)
(c)
CH 3
C  C

4
H SO
2
4
Q.3
What
will
be
major
product
obtained
from
C
CH
addition
of
HBr
to
each
of
the
following
HgSO
(d)

4
compounds.
H SO
2
4
(a) CH
— CH
2 — CH = CH
3
2
CH
CH 2
C
CH
3
H
O
(e)

3
(b)
(c)
CH
3
HgSO
(f)
CH
3 — C  CH

4
— CH = C — CH
(d) CH
3
3
H
2 SO
4
CH
C
CH
3
H
O
(g)

3
(e)
H C =
C
CH
— CH
2
2
3
(f) CH
— CH = CH — CH
3
3
H O
(h)
l-phenyl cyclohexene

3
(g) HO
CH = CH
H O
2
(i)
l-methyl cyclopetene

3
HBr
(j)

(h) CH
— CH
CH
— CH = CH 2
3
2
CH
3
HBr
(k)
Ph — CH
2 — CH = CH
 
2
CCl
4
Find total product in following reaction ? (including
(i)
(j)
stereoisomer)
CH 3
H
(a)
 (x) products
OH
(k)
Br
2
Ans.
(z) (products)
CCl
O
4
O
HBr
 (y) (products) (Markonikoff products)
CCl
4
1.
(a)
(b)
O
OH
(c)
Me
H
HBr
(b)

(A)
 (B)
CCl
4
Br 2
(C)
CCl 4
OH
H
(c)


14

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O O (d) (e)
O
O
(d)
(e)

O

(f) (g)
(f)
(g)
O CHD 2
O
CHD 2

OH

OH (h) Ph (i) Br (j) (k)
OH
(h)
Ph
(i)
Br
(j)
(k)

Br

(e) O (f) (g) O CHD 2 OH OH (h) Ph (i) Br (j) (k) Br

2. (a)

(b)

(c)

(e)

x 3 ; y 2 ; z 5

A 1 ; B 1 ; C 2

3

(d) 2

4

(f) x 4 ; y 4

3.

(a)

(c)

(e)

M. I.

(h)

(j)

(k)

* M. I. (b) Br Br (d)
*
M. I. (b)
Br
Br
(d)

B r Br

I. (h) (j) (k) * M. I. (b) Br Br (d) B r Br * Br

Br

* Br M. I. *
*
Br
M. I.
*

(f)(k) * M. I. (b) Br Br (d) B r Br * Br M. I. *

Br

(g)

HO

I. (b) Br Br (d) B r Br * Br M. I. * (f) Br (g)

Br

Br Br * M. I. (i) Me HO M. I.
Br
Br
*
M. I. (i)
Me
HO
M. I.

Br * (f) Br (g) H O Br Br Br * M. I. (i) Me HO M.

Br

15

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IIT-JEE ChEmistry by N.J. sir

ORGANIC chemistry

DPP NO- 09

Time: 15 minutes

Q.1

Q.2

Q.3

How will prepare following compound using alkene as the starting material ?

(a)

(c)

(e)

(g)

OH

using alkene as the starting material ? (a) (c) (e) (g) OH Br CH 3 OH

Br

CH 3
CH 3
alkene as the starting material ? (a) (c) (e) (g) OH Br CH 3 OH Br
OH
OH

Br

(b)

(d)

Br (f) Br 3
3

CH — O — C — CH

3

CH 3

OHCH 3 OH Br (b) (d) Br (f) 3 CH — O — C — CH

OCH (i) OCH

3

Identify reactant in following reaction

Br (a) (A)  meso – 2, 3 – dibromobutane 2 CCl 4 Br Br
Br
(a)
(A)
 meso – 2, 3 – dibromobutane
2
CCl
4
Br
Br
(b)
(B)

2
+ Mirror Image
CCl
4
Br
HBr
(c)
(C)

CCl
4
Br
Br
HBr
(d)
(D)

CCl
4
CH
3
HBr
(e)
(E)

CH
3 — C — CH
2 — Br
CCl
4
CH
3

(f)

(F)



H O

3

O

CH 2 — Br CCl 4 CH 3 (f) (F)   H O 3 O
HBr (g) (G)  racemic mixture of 2, 3 – CCl 4 dibromobutane. Write –
HBr
(g)
(G)
 racemic mixture of 2, 3 –
CCl
4
dibromobutane.
Write – Mechanism
H
(a)


(b) Ph—CH 2 —CH 2 —OH

OH

Ph — CH — CH 3

3

H O

Ans.

1. (a)

(b)

(c)

(d)

(e)

(f)

(g)

(h)

 H O  3  H O or  3
H O

3
H O
or

3
 H O  3  H O or  3 or or or HBr 

or

 H O  3  H O or  3 or or or HBr 

or

H O  3  H O or  3 or or or HBr  CCl

or

HBr



CCl

4

HBr  or CCl 4 MeOH  HBr  CCl 4 or or
HBr

or
CCl
4
MeOH

HBr

CCl
4
or
or

4 MeOH  HBr  CCl 4 or or MeOH 2. (a) A  Trans but-2-ene

MeOH

2.

(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



H O

3

16

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IIT-JEE Chemistry by N.J. sir

ORGANIC chemistry

DPP NO-10

Time: 15 minutes

OZONOLYSIS:

Example 1:

Mechanism:

The reaction of alkene of alkene with ozone (O 3 ) followed by hydrolysis is known as ozonolysis.

It is two types : (I)

Reductive ozonolysis In presence of reducing agent

Oxidative ozonolysis In presence of oxidizing agent Zn, H 2 O or Zn, CH 3 COOH or (CH 3 ) 2 S or (Ph) 3 P etc. H 2 O 2 or R – C – O – O – H or Ag 2 O etc. |

(II)

Reducing agents:

Oxidising agents:

|

O

R

R

R’ O 3 C = C step I
R’
O 3
C = C
step I

H

–70°C

R

O R’ Zn/H O 2 C C Reductive
O
R’
Zn/H O
2
C
C Reductive
R O O H O 2 2
R
O O
H O
2
2

H

ozonolysis

R

R

C = O + R’– C – H
C = O
+ R’– C – H

O

Oxidative

ozonolysis

[SCT-Cut the double bond

and paste two oxygen atoms

and vice versa]

R – C – R + R’ – C – OH O O
R – C – R
+ R’ – C – OH
O
O
R R R R O O R — C — O C C O +
R
R
R
R
O
O
R
— C — O
C
C
O
+
+
+
O
O
R +
C
R’
— C — O
R’
H
O
H
R
R
O
R — C — O
C
O
O
+
R
O
R’
R – C – R
+ R’ – C – H
C
R’
O = C
H
H
O
O

R’

H

C = O R + R’ – C – H C R’ O = C H H O O
C = O

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.

(i)

(ii)

(iii)

(iv)

(v)

(vi)

[ 7 × 2 = 14]

(i)O 3 H C = CH  2 2 (ii)Zn/H O 2 (i)O 3 CH
(i)O
3
H C = CH

2
2
(ii)Zn/H O
2
(i)O
3
CH
3 — CH = CH

2
(ii)Zn/H O
2
CH
3
(i)O
3

CH
– C = CH
(ii)Zn/H O
3
2
2
(i)O
3

(ii)Zn/H O
2
(i)O
3

(ii)Zn/H O
2
(i)O
3

(ii)Zn/H O
2
H

Q.2

(vii)

H 2 C = CH — CH

(i)O

3



(ii)Zn/H O

2

2 – CH = CH – CH 3

Find out the structure of reactant.

(i)

(ii)

(iii)

X

X

X

[11 × 2 = 22]

(i)O

3

 CH 3 – CH 2 C H

(ii)Zn/H O

2

CH 3 – CH 2 – C – H (ii)Zn/H O 2 O (i)O 3 

O

(i)O

3



(ii)Zn/H O

2

(i)O

3



(ii)Zn/H O

2

H O + H O + O H
H
O +
H
O +
O
H

O

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O O (i)O 3 (iv) X  + (ii)Zn/H O 2 H H (i)O 3
O
O
(i)O
3
(iv)
X

+
(ii)Zn/H O
2
H H
(i)O
3
(v)
X

(ii)Zn/H O
O
2
O
CH 3
(i)O
(vi)
X
+
3

C = O + H
C = O
(ii)Zn/H O
2
H C
H
3

Q.3

(vii)

(viii)

(ix)

(x)

(xi)

X

(i)O

3



(ii)Zn/H O

2

O

O

(ix) (x) (xi) X (i)O 3  (ii)Zn/H O 2 O O O (i)O O 3

O

(i)O O 3 X  + HCHO (ii)Zn/H O O 2 C H 10 12
(i)O
O
3
X

+ HCHO
(ii)Zn/H O
O
2
C
H
10
12
O
O
(i)O
3
X

+
(ii)Zn/H O
2
C
H
12
18
O = C = O +
O + HCHO
O
(i)O
C H
3
 C
H O
6
4
3
2
3
(ii)Zn/H O
2

(X)

C

X

12

H

18

(i)O

3



(ii)Zn/H O

2

O O
O
O

O

+ HCHO

Give the ozonolysis product of the following.

H

O (  ) 3 (i) X  3 Zn O C H O O
O
(
 )
3
(i) X
 3
Zn
O
C
H
O
O
3
(ii)
 ?
Zn/H O
2
How many species will be formed.

(iii)

? Zn/H O 2 How many species will be formed. (iii) O 3 /  

O

3

/



Zn/H O

2

How many species will be formed.

Q.4

How many initial ozonoids are possible in given reaction.

(i)

(i)O

3

/

CH 2 = CH 2



(ii)Zn/H O

2

(ii)

CH 3 – CH = CH – CH 3

(i)O

3

/



(ii)Zn/H O

2

(iii)

CH 3 – CH = CH

2

(i)O

3

/



(ii)Zn/H O

2

Q.9 Only mole of the compound A (molecular formula

12 ), incapable of showing stereoisomerism,

2 on hydrogenation

over Pd. A undergoes ozonolysis to give a

O ). What are the

C H

8

reacts with only one mole of H

symmetrical diketone B(C H 8 12 structure of A and B? O (A) (B) O
symmetrical diketone B(C H
8
12
structure of A and B?
O
(A)
(B)
O
If
after
complete
ozonolysis

2

Ans.

Q.21

of

monomer of natural polymer gives two moles of

of

one

mole

Ans.

CH

3

and one mole of O = C CH = O .

Identify

the monomer and draw the all-cis structure of

natural polymer.

CH 2 O

[IIT '2005]

(a)

CH

CH 3

2 = C – CH = CH

2

CH  3 (b) C = C (CH  2
CH 
3
(b) C = C
(CH 
2

H

CH 2 ) n

OH H   , (i)O Q.22  X  Y 3 (ii) Zn /
OH
H
 
,
(i)O
Q.22

X
 Y
3
(ii) Zn / Cl COOH
3
Identify X and Y.
O
Ans.
(X)
, (Y)
CH
– C – (CH )
4 – CH = O
3
2

CH

3

18

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IIT-JEE ChEmistry by N.J. sir

ORGANIC chemistry

DPP NO-11

Time: 15 minutes

Q.1

O CHO CHO O
O CHO
CHO
O

CHO

is obtained by the ozonolysis of following?

(A) (B) (C) (D)
(A)
(B)
(C)
(D)

Q.2

Q.3

Q.4

Which starting material should be used to produce

the compound shown below?

H O O O O (B) (D)
H
O
O
O
O
(B)
(D)

(A)

O ?  3 H Zn  H O 2
O
?

3
H
Zn
H O
2

(A)

(C) CH 3 | H   CH — C — CH 3  |
(C)
CH
3
|
H

CH — C — CH
3
| 3

O

(P) + HCHO

3

Zn,H O

2

OH

Product (P) is

O

||

CH — C — CH

(A) CH 3 — CH 2 — CHO (B)

(C) CH — CH — OH

3

(D) CH 3 — CHO

3

|

CH

3

3

The reactants that lead to product (a) and (b) on

ozonolysis are

O O CHO
O
O
CHO
(a) (A) (B)
(a)
(A)
(B)

HCHO

(b)

and (b) on ozonolysis are O O CHO (a) (A) (B) HCHO (b) Q.5 Q.6 Q.7

Q.5

Q.6

Q.7

Q.8

(C) (D)
(C)
(D)
O O CHO (a) (A) (B) HCHO (b) Q.5 Q.6 Q.7 Q.8 (C) (D) This compound

This compound on ozonolysis gives which of the following compounds

O

on ozonolysis gives which of the following compounds O (I) O O O (II) O O

(I)

O O O (II) O O
O
O
O (II)
O
O

O

(III)

of the following compounds O (I) O O O (II) O O O (III) (IV) O

(IV)

O

OHC—C—C—CH —C—CHO

2

O O O OHC—C—C—CH —CH = O 2
O
O
O
OHC—C—C—CH —CH = O
2

O

(A)

(C)

I, II, III & IV

I, II, III

(B) I, III, IV

(D) I, II, IV

Which of the following will give three different

compounds on ozonolysis

(A)

(C)

(B)will give three different compounds on ozonolysis (A) (C) (D) Me Me Which one of the

(D)give three different compounds on ozonolysis (A) (C) (B) Me Me Which one of the following

Me Me
Me
Me

Which one of the following compounds gives

acetone (CH ) C=O as one of the products of its

ozonolysis?

3

2

(A)

(B)(CH ) C=O as one of the products of its ozonolysis? 3 2 (A) (C) (D)

) C=O as one of the products of its ozonolysis? 3 2 (A) (B) (C) (D)

(C)

(D)as one of the products of its ozonolysis? 3 2 (A) (B) (C) Sentene ozonolysis 

one of the products of its ozonolysis? 3 2 (A) (B) (C) (D) Sentene ozonolysis 

Sentene

ozonolysis



O O
O
O

Which is the correct structure of Sentene.

Q.9

(A) (B)
(A)
(B)

(C)

(D)Which is the correct structure of Sentene. Q.9 (A) (B) (C) In which of following reaction

is the correct structure of Sentene. Q.9 (A) (B) (C) (D) In which of following reaction

In which of following reaction product formed is aromatic

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(A)

(B)

OH

 HBr  HBr

 HF  HF

(C)  KH  OH (D)  H SO  2 4 HO
(C)
 KH 
OH
(D)
 H SO 
2
4
HO

OH

Q.10 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-2- methylpropane 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 Cl 2 in similar conditions. (Round answer to nearest integer)

IIT-JEE ChEmistry by N.J. sir

ORGANIC chemistry

DPP NO-12

Time: 15 minutes

Free Radicals:–

Wurtz Reaction:–

R — X

Na

 R— R

ether

Mechanism:– (Free radical Mechanism)

+ – (1) Na Na + e  (2) R — X + e –
+
(1)
Na Na
+ e
(2)
R — X
+ e
– R +
X
(3)
R +
R R — R
(Ionic Mechanism)
+
(1)
Na Na
+ e
(2)
R — X
+ 2e
–  R+
X

(3)
R  + R — X R — R +
X
Na
Q.1
CH 3 — Cl

ether
Na
Q.2
Et — Cl 
ether
Na
Q.3
CH 3 — Cl + Et — Cl

ether
Na
Q.4
(Ph) 3 CI

ether
Na
Q.5
I 
ether
Na
Q.6
Cl
Br

ether
Br
Na
Q.7

ether
Br
:
:
:

Q.8

Q.9

Q.10

Q.11

Q.12

Q.13

Q.14

Q.15

Q.16

Q.17

Q.18

Na  ether Cl Cl Cl Na  ether Br Na  Cl Cl ether
Na

ether
Cl
Cl
Cl
Na

ether
Br
Na

Cl
Cl
ether
Cl
Na

Cl
ether
Na Ph — Cl  THF Na Cl + Cl — CH  3 THF
Na
Ph — Cl

THF
Na
Cl + Cl — CH

3
THF
Cl
Na

ether
Cl
Zn
CH —CH
2

2
Br
Br
Cl
Ag/Powder
H—C—Cl

Cl
Na

CH —CH=CH—CH
ether
2
2
Br
Br
I
I

Br

Na



ether

(fitting Reaction)

(Wurtz fitting)

20

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ETOOS Academy Pvt. Ltd.

F-106, Road No. 2, Indraprastha Industrial Area, End of Evergreen Motors (Mahindra Showroom), BSNL Office Lane, KJhalawar Road, Kota, Rajasthan (324005)

IIT-JEE ChEmistry by N.J. sir

ORGANIC chemistry

DPP NO-13

Time: 15 minutes

Q.1.

Q.2.

Q.3

Q.4.

Q.5.

Q.6

Q.7.

Q.8.

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 o hydrogen in neopentane compare with the of a 1 o hydrogen in ethane? Give product(s) in each of the following reactions

CH 3 CH CH 2 CH 2 CH 3

the following reactions CH 3 CH CH 2 CH 2 CH 3  (A) 2 Br

 (A)

2

Br

/ hv

CH 3

Bromination of methane is slowed down by addition of fairly large amount of HBr.

(a)

(b)

Suggest a possible explanation for this.

Account for the fact that addition of HCl does not have a similar effect upon chlorination of CH 4 .

Which of the following compounds on gentle heating, will undergo homolytic bond cleavage easily:

(A)

(C)

O

(CH O C 3 ) 2 C (CH ) C ─ C H 3 3
(CH
O
C
3 )
2 C
(CH ) C ─ C H
3
3
6
5

CH

3

(B)

(D)

(CH 3 ) 3 C ─ OC(CH 3 ) 3

(CH 3 ) 3 C ─O─O─C(CH 3 ) 3

Amongst the following, the most basic compound is:

(A) C 6 H 5 NH 2

Which of the following is most acidic?

(B) p-NO 2 ─C 6 H 4 NH 2

(C) m-NO 2 ─C 6 H 4 NH 2

(A)

NH 2
NH
2

(B)

CH 3 NH 3

(C)

NH 3
NH
3

Write mechanism of following reactions?

(a)

- HC
-
HC

(b)

Ph

3

C─Cl

Na



 

Et O

2

Cl

Na CH 2 Et 2 O
Na
CH
2
Et
2 O



Ph

2

C

2

  Et O 2 Cl Na CH 2 Et 2 O  Ph 2 C 2

CH

CPh 2

(D) C 6 H 5 CH 2 NH 2

(D)

NH 3
NH
3

Arrange the following in increasing order of stability.

(a)

, , , ,
,
,
,
,
 
   

(regarding stability of free radical)

 
   

CH

3

(b)

CH

CH 2
CH
2

CH

 
CH CH CH 2 2
CH
CH
CH
2
2

CH

,

,
 
CH
CH

2

2

2

,