Page No # 1

This DPP & CT-3 is to be discussed (29-04-2014)

DPP No. # 06 (JEE-ADVANCED)
Total Marks : 169 Max. Time : 118 min.
Single correct Objective ('1' negative marking) Q.1 to Q.15 (3 marks, 2 min.) [45, 30]
One or more correct objective (no negative marking) Q.16 to Q.20 (4 marks, 2 min.) [20, 10]
Single digit integer type ('1' negative marking) Q.21 to Q.25 (4 marks, 3 min.) [20, 15]
Double digit integer type (no negative marking) Q.26 to Q.29 (4 marks, 3 min.) [16, 12]
Assertion and Reason ('1' negative marking) Q.30 to Q.32 (3 marks, 3 min.) [09, 09]
Comprehension ('1' negative marking) Q.33 to Q.41 (3 marks, 2 min.) [27, 18]
Match the Following (no negative marking) Q.42 to Q.45 (8 marks, 6 min.) [32, 24]
1. C NH
2
||
O

!
" " " # "
10 4
O P
P
$
" " " " # "
O H
MeMgBr
3
Q " " " " " # "
2 2
I , ) OH ( Ca
R, compound R is :
(A) C CH
3
||
O
(B)
COOH
(C) C
||
O
(D)
2.
COOH
(I) PCl
5
X
(II) H ,Pd/BaSO
2 4
(III) HCN
(III) H O
3
+
; X is :
(A) COOH CH Ph
|
OH
% % (B) 3
CH CH Ph
|
OH
% %
(C) COCl CH Ph
|
OH
% % (D)
COOH CH CH
|
OH
3
% %
3.
O
Me
Me
OH

X
H SO
2 4
CH OH, H O
3 2
; X is :
(A)
Me
OH
OH
Me
(B)
Me
OH
Me
OH
(C)
Me
OH
OH
Me
(D)
OH
OH
TARGET : JEE (ADVANCED) 2014
TEST SYLLABUS
Date : 30.04.2014 TEST : PART TEST-3 (PT-3)
Syllabus : Aromatic compound, Carbonyl compound, Carboxylic acids
& their derivatives, Grignard reagent.
Course : VIJETA (JPAD)
& VIJAY (JRAD)
Date : 27-04-2014
DPP No. : 06
ORGANIC CHEMISTRY
Page No # 2
4.
M
HNO
3
H SO
2 4
N
HNO
3
H SO
2 4
O
(NH ) S
4 2
P
NaNO ,HCl
2
0C
H O,
2
Q
Sn ,HCl
R ; R is :
(A)
OH
NH
2
(B)
OH
NO
2
(C)
OH
NH
2
(D)
OH
NH
2
5. Compound A (C
10
H
14
O) does not react with Br
2
water, acetyl chloride or boiling NaOH solution. On reaction
with excess of HI, A is converted into B (C
3
H
7
I) and C (C
7
H
7
I). B can be hydrolysed by aq. NaOH to D
(C
3
H
8
O) which gives iodoform test. C can be oxidized to carboxylic acid E (C
7
H
6
O
2
) by chromic acid. Assign
structures to A.
(A) PhCH
2
O Pr (B) PhCH
2
O iPr (C) Ph

O iPr (D) PhCH
2
CH
2
iPr
6. A mixture of two aromatic compounds (A) and (B) was separated by dissolving in chloroform followed by
extraction with aqueous KOH solution. The organic layer containing compound (A) when heated with
alcholic solution of KOH produced a compound C (C
7
H
5
N), associated with an unpleasant odour. The
alkaline aqueous layer on the other hand, when heated with chloroform and then acidified gave a mixture of
two isomeric compounds (D) and (E) of molecular formula C
7
H
6
O
2
. Identify (A).
(A) PhNC (B) PhOH (C) PhNH
2
(D) Salisaldehyde
7. Which can be the product of the following reaction ?
+
(A) (B) (C) (D)
8. S
1
: Diazocoupling in aniline is carried out in sightly acidic medium.
S
2
: Carbonyl compounds undergo electrophilic as well as nucleophilic addition reaction.
S
3
: Secondary amines give insoluble precipitate with aqueous alkaline PhSO
2
Cl.
S
4
: Benzaldehyde reacts faster with grignard reagent than benzene-1,2-dicarbaldehyde.
(A) FTFT (B) TTFT (C) TTTF (D) TFTF
Page No # 3
9. The intermediate of the following reaction is :
(A) (B) (C) (D)
10. Consider the following sequence of reaction and identify the end product(R) :
COOH
CH Ph
2
SOCl
2
P
AlCl
3
Q
Zn-Hg
R
HCl
(A)
O
Ph
O
(B)
Ph
O
(C) (D)
11. In the following sequence of reactions;
Ph
Ph
M
O
N PhCH OH + PhCOO
2

M + N
O
3
Zn/H O
2
Q .
The compound Q is :
(A) PhCH
2
CH=CHPh (B)
Ph
Ph
=CHCH
3
(C)
Ph
=CHPh
(D) PhCH=CHPh
Page No # 4
12. Observe the following reaction;
Br CH C C OH
2
|
| ||
CH
3
O
CH
3
+ Na
2
CO
3
"# "
!

Br CH C C O
2
..
- | ||
CH
3
O
|
CH
3

"# "
CH = C
2
CH
3
CH
3
+ HBr + CO
2
What will be the product of following given reaction ?
Br Br
| |
OH C CH CH Ph
||
O
% % % %

Alc. KOH
heat
"""""#
(A)
Br
|
COOH C CH Ph % & % (B)
PhC=CH
2
Br
(C) Ph CH = CH Br (D) Ph C ' C COOH
13. Predict the major product of given reaction.

N H /KOHH O
2 4 2
(Wolf-kishner reduction)
(A)
Major
Product A is :
(A) (B)
(C) (D)
14.
) A (
H
!
" "# "
$
, Product (A) is :
(A) (B) (C) (D)
O
| |
Page No # 5
15.
OH OH
OH OH
OH O
, This conversion can be achieved by :
(A) Me
2
CO/H
+
, H
3
O
(
, KMnO
4
/HO

(B) Me
2
CO/H
+
, KMnO
4
,H
3
O
$
(C) KMnO
4
/NaO
4
,

Me
2
CO/H
+
, H
3
O
+
(D) KMnO
4
/NaIO
4
, H
3
O
+
, Me
2
CO/H
+
16. Compound A (C
5
H
7
OCl) reacts rapidly with ethanol and catalytic amount of acid to form a plesant smelling
substance, B (C
7
H
12
O
2
) . A also reacts with H
2
O to form C with neutralisation equivalent of 100. A,B and C
all react with Br
2
water. Acid C, which can also be obtained by acidic hydrolysis of B is oxidised to new acid
D (C
4
H
6
O
3
) and CO
2
. D on heating with soda lime gives acetone. Identify A to D .
(A) A = CH C CH C Cl
3 2
CH
2
O
(B) B = CH C CH C OEt
3 2
CH
2
O
(C) C = CH C CH C COOH
3 2
CH
2
O
(D) D =
17. Identify A,B,C,D,E and F in the following :
A(C H NO Cl )
7 5 2 2
Sn + HCl
B
NaNO / HCl
2
CAN is
(Ceric Ammoium Nitrate)
D
oxidation
E(acid) F
CAN
C (colour)
HNO / H SO
3 2 4
G (single mononitro derivative)
soda lime
(A) A =
Cl
Cl
CH NO
2 2
(B) D =
Cl
Cl
CH OH
2
(C) F =
Cl
Cl
(D) G =
Cl
18. Identify A,B,C, and D in the following :
(A) D is Cis (B) D is trans (C) B is Cis (D) B is trans
Page No # 6
19. Primary (1) amine group is formed in :
(A)
" " " # "
NaHS
(B)
" " " " # "
KOH / Br
2
(C)
" " " " " " " " # "
! / O Cu / NH CH
2 2 3 (D)
" " " # "
HCl / Zn
20.
CONH
2
Which statement(s) is/are correct :
(A) Reduced product of P and Q will be metamers to each other.
(B) By dry distillation of hydrolysed products of P with Ca(OH)
2
, gives benzophenone.
(C) Hydrolysed product of Q, reacts with NaNO
2
+ HCl followed by reaction with phenol, gives orange red
dye.
(D) Electrophile involved in the formation of Q is dichlorocarbene.
21. Number of electrophilic substitution which takes place when salicylic acid is reacted with bromine water ?
22. The number of stereoisomers of the product obtained in the following reaction is :
) (
Me
|
O CH CH Ph
)
& % % +
23. In the following sequence of reaction number of Nucleophilic substitution is :
24.
!
!
" " " " " " " # "
/ SO H . dil ) 2 (
/ O ) 1 (
4 2
2
?
Total number of organic products formed (major, minor all).
Page No # 7
25.
" " # "
3
O

excess
H / OH NH
2
" " " " " # "
(
The total number of isomeric products (including stereomers) formed at the end of the reaction is :
26. How many aromatic diazonium chlorides of xylene can be reduced to meta-xylene by H
3
PO
2
?

" " " " # "
! , PO H
2 3
(m-Xylene)
27. Find the total number of groups with which the Grignard Reagent (CH
3
MgBr) can react.
28. How many types of Grignard reagent can be used to prepare the following alcohol, by using different Ketones.
OH
|
) Me ( CH C Me
|
Et
2
29. Observe the following reaction,
'X'
) 1 (
HCl . OH NH
2
" " " " " # "

) 2 (
SO H
4 2
" " " # "

) 3 (
boil , KOH
" " " " # "

) 4 (
ion Acidificat H
" " " " " " " # "
$
H
2
N CH
2
CH
2
CH
2
COOH
molecular mass of 'X' is :
30. Statement-1 : NaHSO
3
is used in seperation and purification of aldehydes.
Statements-2 : NaHSO
3
is reducing agent.
(A) Statement-1 is True, Statement-2 is True; Statement-2 is a correct explanation for Statement-1.
(B) Statement-1 is True, Statement-2 is True; Statement-2 is NOT a correct explanation for Statement-1.
(C) Statement-1 is True, Statement-2 is False.
(D) Statement-1 is False, Statement-2 is True.
31. Statement-1 : CCl
3
CHO forms an isolable crystalline hydrate.
Statement-2 : Electron withdrawing chlorine atoms stabilise hydrate by intramolecular H-bonding.
(A) Statement-1 is True, Statement-2 is True; Statement-2 is a correct explanation for Statement-1.
(B) Statement-1 is True, Statement-2 is True; Statement-2 is NOT a correct explanation for Statement-1.
(C) Statement-1 is True, Statement-2 is False.
(D) Statement-1 is False, Statement-2 is True.
Page No # 8
32._ S t a t e m e n t -1 : CH
3
MgBr can not be prepared in cold aqueous solution.
Statement-2 : Water molecules stablise grignard molecules by Hbonding.
(A) Statement-1 is True, Statement-2 is True; Statement-2 is a correct explanation for Statement-1.
(B) Statement-1 is True, Statement-2 is True; Statement-2 is NOT a correct explanation for Statement-1.
(C) Statement-1 is True, Statement-2 is False.
(D) Statement-1 is False, Statement-2 is True.
Comprehension # 1
Methyl red is commonly used as indicator for acid base titrations. It is prepared by treating NaNO
2
/HCl with
anthranilic acid and the resulting solution is mixed with N,N dimethylaniline and shaked well the solution for
some minutes to get Methyl Red.
Given : (anthranilic acid)
33. Which is most likely to be Methyl Red ?
(A) (B)
(C) (D)
34. The two organic materials anthranilic acid and N,N dimethylaniline used in preparation of methyl Red can be
best distinguished by :
(A) HCl solution (B) Br
2
water (C) CHCl
3
/KOH (D) FeCl
3
Comprehension # 2
The relative comparision of equilibrium constants of addition of RMgBr on four carbonyl compounds has been
shown by the graph below.
35. Which compound corresponds to H if the four given compounds are :
(A) P NO
2
C
6
H
4
CHO (B) C
6
H
5
CHO (C) P MeOC
6
H
4
CHO (D) CH
3
COCH
2
CH
3
36. Which compound corresponds to G if the four given compounds are :
(A) CH
3
CHO (B) C
6
H
5
COCH
3
(C) C
6
H
5
CHO (D) C
6
H
5
COC
6
H
5
Page No # 9
Comprehension # 3

3
2 2 3
AlCl
Cl CH CH CH
" " " " " " # "
X $
" "# "
O H
O
3
2
+
37. Which of the following compound is 'P' ?
(A) (B) (C) (D)
38. S is a well known pain killer which of the following is 'R' ?
(A) (B) (C) (D)
Comprehension # 4
Observe the following sequence of reaction
Y
CHCl /NaOH
3
Z
(2) H O
2
W
(H O)
2
U
O
3
Zn/H O
2
X
39. The product Y is
(A)
O
(B)
O
(C)
OH
(D)
OH
40. The product U is
(A)
O
O
(B)
O
O
(C)
O
O
(D)
O
O
Page No # 10
41. Compound on reaction with CO
2
/NaOH followed by CH CCl
3
O
and pyridine produces :
(A)
COOH
OCOCH
3
(B)
COOH
OCOCH
3
(C)
COOH
COOCH
3
(D)
COOH
COOCH
3
42. Column-I Column-II
(A)
" " " # "
*
OH
(p) Aromatic ring substitution
(B)
" " " " " " " # "
*
& OH / O CH CH
3 (q) Nucleophilic addition
(C)
" " " " " " # "
$
4 2 3
SO H HNO
(r) Condensation reaction
(D)
" " " " # "
(
H / KCN
(s) Formation of more than one organic products
43. Match the column
Column I Column II
(A) MeCO(CH
2
)
4
COMe
!
$
*
" " " # "
/ H ) ii (
OH ) i (
(p)
(B) (CH
2
)
4
" " # "
*
OEt
(q)
(C) PhCHO +
" " " " # "

3
COO CH
(r)
OH
|
COO C ) Ph (

2
(D) PhCOCOPh
" " # "
*
OH
(s)
Page No # 11
44. Column-I Column-II
(Reactions) (Features)
(A)
4
SO
2
H
3
HNO
" " " # "
(p) K
H
/K
D
= 1
(B)
" " " # "
Fe /
2
Cl
(q) K
H
/K
D
> 1
(C)
" " " " " # "
4
SO
2
H . Conc
(r) Deactivated reactant
(D)
" " " " " # "
(
H / OH
5
H
2
C
(s) Ortho and para substituted products are major
(t) Meta substituted product is major.
45. Column I Column II
(Compounds) (Type of possible reactions)
(A) (p) Nucleophilic addtion
(B) (q) Aliphatic nucleophilic substitution
(C) (r) Elimination
(D) (s) Electrophilic addition reaction
(t) Electrophilic substitution reaction