Ranjeet Shahi

R RR R a aa a n nn n j jj j e ee e e ee e t tt t S SS S h hh h a aa a h hh h i ii i C CC C h hh h e ee e m mm m i ii i s ss s t tt t r rr r y yy y C CC C l ll l a aa a s ss s s ss s e ee e s ss s
S CO 4 8 , I I
n d
Fl o o r , S e c t o r 2 0 C, CHANDI GARH Ph : 2 7 2 5 7 4 8 , 3 0 4 0 6 6 0
S C F 7 2 , S e c t o r 1 0 , P a n c h k u l a , P h : 3 9 1 4 8 4 4 T e s t - 4
1

PRACTICE TEST CHEMISTRY PRACTICE TEST CHEMISTRY PRACTICE TEST CHEMISTRY PRACTICE TEST CHEMISTRY
Duration: Two hours
MM: 178

S CO 4 8 , I I
n d
S C F 7 2 , S e c t o r 1 0 , P a n c h k u l a , P h : 3 9 1 4 8 4 4 T e s t - 4 A
2
f ff for IIT-JEE 2010
Section-A
1.
Which of the following compounds has highest enol content?
(a) (b) (c) (d)
O
CHO
O
O O

D
2.
Treatment of 1-pentol with excess of 1) BH
3
2) NaOH, H
2
O
2
will provide (major product):
OH
H
OH
OH
CHO
OH
OH
O
OH
H
OH
OH
H
OH
OH
CHO
OH
OH
O
OH
I II III
IV
V
VI
1-pentol

(a) I (b) I, II (c) III, IV (d) I, II, V, VI

A
3.
C
8
H
10
hydrocarbon is nitrated by HNO
3
and sulfuric acid. Two, and only two, C
8
H
9
NO
2
isomers are obtained. Which
of the following fits this evidence?
(a) ethylbenzene (b) ortho-xylene (c) meta-xylene (d) para-xylene

B
4.
The most reactive and the least reactive arene towards HNO
3
+H
2
SO
4
(both concentrated) are respectively:
C H
3
NH Cl
NO
2
NO
2
Br Br
Br
C CH
3
O
I II III IV

(a) I&IV (b) I&III (c) II&III (d) II&IV

B
5.
What is the major product obtained from the following reaction?
CH
3
ONa CH
3
CH
2
Br
H
3
O+
O
O O
CH
3
OH
heat

(a)
(b) (c) (d)
OH
O O
O
OH
O
O
OH
O

A
6.
Which of the following reaction cant produce acetamide?
(a) (CH
3
CO)
2
O + NH
3
(b) CH
3
CHO + NH
3
(c) CH
3
COBr + NH
3
(d)CH
3
COOCH
3
+NH
3

B
7.
Which of the followings compounds will most readily give a cyclic product when treated with a base?
(a) (b) (c)
RO OR
O O
RO OR
O O
CH
3
CH
3
RO
OR
O
O
RO
OR
O
O CH
3
CH
3
(d)

C

S CO 4 8 , I I
n d
3
8.
The major product of the following reaction is:
NH
2
O
2
N
NaNO
2
/HCl
C H
3
OH
N N C H
3
NO
2
(a) (b)
C H
3
NO
2
(c) N N
OH
CH
3
O
2
N
N N
CH
3
OH NO
2
(d)
0
o
C

C
9.
An equimolar mixture of benzoic acid and benzyl alcohol is dissolved in equal volumes of ether and 5% aqueous
NaOH. The resulting mixture separates into two immiscible liquid layers. Which of the following is approximately
correct?
(a) both organic solutes are largely in the ether layer (b) both organic solutes are largely in the water layer
(c) the benzyl alcohol is in the ether layer and the benzoic acid is in the water layer
(d) the benzyl alcohol is in the water layer and the benzoic acid is in the ether layer

C
10.
Fischer esterification of phenylacetic acid with 1-propanol gave a mixture of 93% of the ester, propyl phenylacetate,
contaminated with 7% unreacted acid. Which of the following treatments would be best used to purify the ester?
(a) reduce the unwanted acid with LiAlH
4
in ether.
(b) wash an ether solution of the crude product with concentrated brine (aq. NaCl).
(c) wash an ether solution of the crude product with 5% aqueous sulfuric acid.
(d) wash an ether solution of the crude product with 5% aqueous sodium carbonate.

D
11.
Which of the following is an intermediate in the Fischer esterification of propanoic acid with ethanol?
(a) 1-propoxy-1,1-dihydroxyethane (b) 2-propoxy-1,1-dihydroxyethane
(c) 1-ethoxy-1,1-dihydroxypropane (d) 2-ethoxy-1,1-dihydroxypropane

C
12.
Which statement regarding isotope exchange of
18
OH
2
with the oxygen of a carboxyl group is correct?
(a) no exchange occurs under any circumstances
(b) base-catalyzed exchange is more effective than acid-catalyzed exchange
(c) acid-catalyzed exchange is more effective than base-catalyzed exchange
(d) acids and bases are equally effective in catalyzing an exchange

D
13.
The major organic product of the following reaction is:
O
CHO
NaOH
(CH
3
)
2
CuLi
OH
2

(a) (b)
(c) (d)
O
CH
3
Ph
OH
Ph
CH
3
Ph
CH
3
Ph

B
14.
Reduction of 4-oxobutyric acid(X), also called succinic semialdehyde, by sodium borohydride followed by aqueous
acid gives?
18
O
OH
H
O
(i) NaBH
4
/H
2
O
(ii) dil. H
2
SO
4
X

(a) (d) (b) (c)
O
O
O
18
O
O H
18
O
O
18
O
O
18

C
15.
Which sequence of reactions would be best for the conversion of toluene into para-bromophenylacetic acid?
(NBS = N-bromosuccinimide )
(a) i) Br
2
& FeBr
3
; ii) KMnO
4
& heat; iii) NaCN in ethanol; iv) H
3
O
(+)
& heat
(b) i) Br
2
& FeBr
3
; ii) NBS in CCl
4
; iii) Mg in ether followed by CO
2
; iv) H
3
O
(+)

(c) i) Br
2
& FeBr
3
; ii) NBS in CCl
4
; iii) NaCN in ethanol; iv) H
3
O
(+)
& heat
(d) i) Br
2
& FeBr
3
; ii) KMnO
4
& heat; iii) Mg in ether followed by CO
2
; iv) H
3
O
(+)

C

S CO 4 8 , I I
n d
4
16.
What is the expected product from the reaction sequence drawn below?
O
O
O
AlCl
3
Heat
C
10
H
10
O
3
(i) Zn(Hg), HCl
(ii) SOCl
2
AlCl
3
Heat
+
?

(a) (d) (b) (c)
O O
O
O

C
17.
A mixture is comprised of the three compounds shown below:
This mixture is dissolved in diethyl ether, an organic solvent. The organic solution
is extracted with dilute aqueous HCl. After separation of the aq. layer from the
organic layer(A), the aq. solution is set aside. The organic solution(A) is then
extracted with dilute aqueous NaOH. Once again, after separation of the organic
layer(B), the aq. solution is set aside. Which compound or compounds remain
dissolved in the diethyl ether solution A and B?
(a) A-I and II; B-I (b) A-I and III; B-I (c) A-II and III; B-II (d) A-III; B-None

CH
3
NO
2
NH
2
CH
3
OH
CH
3
(I) (II)
(III)

B
18.
Predict major product of the following
reaction:
O
COOH
COOH
(i) Heat
(ii)CH
2
N
2
(1.0 equivalent)

(a) (d) (b) (c)
O
COOCH
3
COOH
O O
COOCH
3
COOH
O

B
19.
Which of the following is true regarding role of NO in nitrosobenzene when it is subjected to aromatic electrophilic
substitution reaction:
(a) meta directing and deactivating (b) ortho/para directing and deactivating
(c) meta directing and activating (d) ortho/para directing and activating

B
20.
Which of the following compounds undergoes nucleophilic substitution most readily?
Cl
COCH
3
(a) (b)
Cl
(c)
Cl
C H
3
(d)
Cl
O
2
N

D
21.
One of the completions A to D is incorrect. Choose the letter corresponding to the incorrect completion.
In the nitration of benzene by concentrated sulphuric and concentrated nitric acid
(a) the reaction is irreversible. (b) the rate determining step is the removal of H
+
from the intermediate.
(c) the attacking electrophile is NO
2
+
. (d) the 2
nd
nitro group enters the benzene ring meta to the first nitro group

B
22.
Choose the statement that is correct concerning the following reaction:
Phenol + CH
3
I/NaOH Major product
(a) This reaction results in methylation of oxygen in phenol. It is utilized frequently because the hydroxide group is
often highly activated. This reaction can be reversed with HI.
(b) This reaction results in methylation of oxygen in phenol. The resulting product is activated approximately the
same amount as in phenol. The reaction can be reversed with HI.
(c) This reaction results in methylation of oxygen in phenol. The resulting product is more highly activated than
phenol. This reaction can be reversed with HI.
(d) This reaction results in an SN-2 reaction between methyl iodide and NaOH. The resulting iodide ion substitutes
at ortho and para positions of phenol. Treatment of this product with Mg will give Grignard reagent.

A

S CO 4 8 , I I
n d
5
23.
Rank the following compounds in decreasing order of reactivity in electrophilic aromatic substitution reaction:
O
O
N
H
O
(I) (II) (III) (IV)

(a) IV > I > III > II (b) III > I > IV > II (c) I > III > IV > II (d) III > II > I > IV

B
24.
Select the best reaction sequence to accomplish the following transformation:
NH
2
HNO
3
H
2
SO
4
Cl
O
AlCl
3
Zn(Hg), HCl
excess
(a) (b)
HNO
3
H
2
SO
4
Cl
AlCl
3
Zn(Hg), HCl
excess
(c)
HNO
3
H
2
SO
4
Cl
O
AlCl
3
Zn(Hg), HCl
excess
Zn(Hg)
ClH
HNO
3
H
2
SO
4
Cl
O
AlCl
3
Zn(Hg), HCl
excess
(d)

D
25.
Two equivalents of the Wittig reagent (CH
3
)
2
C=CH-CH=P(C
6
H
5
)
3
were allowed to react with a C
4
H
4
O
2
compound.
The chief product was 2,11-dimethyl-2,4,6,8,10-dodecapentaene, (CH
3
)
2
C=CH(CH=CH)
3
CH=C(CH
3
)
2
. What was
the C
4
H
4
O
2
compound used in this reaction?
(a) 2-butyne-1,4-diol (b) 1,2-cyclobutanedione (c) 1,3-butadien-2,3-diol (d) 2-butenedial

D
26.
You have two C
6
H
10
O ketones, I and II. Both are optically active, but I is racemized by treatment with base and II is
not. Wolff-Kishner reduction of both ketones gives the same achiral hydrocarbon, formula C
6
H
12
. What reasonable
structures may be assigned to I and II?
(a) I is 3-methyl-4-penten-2-one; II is 4-methyl-1-penten-3-one
(b) I is 2-methylcyclopentanone; II is 3-methylcyclopentanone
(c) I is 3-methylcyclopentanone; II is 2-methylcyclopentanone
(d) I is 2-ethylcyclobutanone; II is 3-ethylcyclobutanone

B
27.
Which of the following reaction sequences would be best for preparing 2,2-dimethyl-3-hexanone from butanal?
(a) (i) addition of tert-butylmagnesium bromide in ether; (ii) hydrolysis workup; (iii) PCC in CH
2
Cl
2

(b) (i) NaBH
4
; (ii) PBr
3
; (iii) Mg in ether; (iv) 2,2-dimethylpropanal, followed by hydrolysis
(c) (i) Wittig reaction with (C
6
H
5
)
3
P=C(CH
3
)
2
; (ii) BH
3
in THF; (iii) H
2
O
2
& base; (iv) PCC in CH
2
Cl
2

(d) (i) Wittig reaction with (C
6
H
5
)
3
P=CHC(CH
3
)
3
; (ii) BH
3
in THF; (iii) H
2
O
2
& base; (iv) PCC in CH
2
Cl
2

A
28.
Which of the following procedures would not be suitable for preparing 3-methyl-1-phenyl-1-butanone,
C
6
H
5
COCH
2
CH(CH
3
)
2
?
(a) (i) C
6
H
5
COCH=CHCH
3
+ (CH
3
)
2
CuLi in ether; (ii) H
3
O
+
workup
(b) (i) benzene + (CH
3
)
2
CHCH
2
COCl & AlCl
3
(ii) H
3
O
+
workup
(c) (i) C
6
H
5
MgBr + (CH
3
)
2
CHCH
2
CHO in ether; (ii) H
3
O
+
workup; (iii) PCC in CH
2
Cl
2

(d) (i) (CH
3
)
2
CHMgBr + C
6
H
5
COCH
3
in ether; (ii) H
3
O
+
workup; (iii) PCC in CH
2
Cl
2

D
29.
Reduction of 4-oxobutyric acid, also called succinic
semialdehyde, by sodium borohydride followed by
aqueous acid gives a C
4
H
6
O
2
product.This product is
which of the following compounds?
O
O
O
O
O
OH
O
O
(a) (b) (c) (d)

D
30.
A C
7
H
9
N base reacts with sodium nitrite and hydrochloric acid at 0 C, giving a clear solution. On heating with KCN
and Cu
2
(CN)
2
a gas evolves, and continued heating with conc. HCl yields a C
8
H
8
O
2
crystalline acid. Heating this
acid with aqueous KMnO
4
produces a C
8
H
6
O
4
product, which dehydrates on strong heating to give a crystalline
C
8
H
4
O
3
compound. What is the C
7
H
9
N base?
(a) benzylamine (b) N-methylaniline (c) para-aminotoluene (d) ortho- aminotoluene
D

S CO 4 8 , I I
n d
6
Section-B

Following Five Questions may have more than one correct answer.

31. Which of the following will produce more than one stereomers of aldol in aldol condensation reaction?
(a) CH
3
CHO (b) Acetone (c) Cyclopentanone (d) C
6
H
5
CHO

A
C
32. Which of the following are more reactive than unsubstituted Benzaldehyde in a Perkin reaction?
(a) p-chloro Benzaldehyde (b) p-aminobenzaldehyde
(c) p-methoxy Benzaldehyde (d) benzene-1,4-dicarbaldehyde

A
D

33. Which of the following will be reduced in Cannizzaro reaction with C
6
H
5
CHO?
(a) p-methoxy Benzaldehyde (b) p-methyl Benzaldehyde
(c) m-chloro Benzaldehyde (d) p-aceto Benzaldehyde

C
D

34. Which of the following have meta-directing, deactivated aromatic ring?
(a)
CF
3
(b)
CONH
2
(c)
OCOCH
3
(d)

A
B

35. Which of the following compounds is(are) more reactive than chlorobenzene in reaction with NaCN(aq)?
(a)
CF
3
Cl
(b)
Cl
Cl
(c)
Cl
NH
2
(d)
Cl

A
B

Section-C

Following Five questions consist of a assertion followed by the reason:
In each question, choose the correct description and reason from the list below:
(a) The statement and reason are both factually true, and reason is the correct explanation of statement.
(b) The statement and reason are both factually true, but the reason is not correct explanation of statement.
(c) The statement is true but the reason is false. (d) The statement is false but reason is true.

36. Assertion: A 2
o
-amide does not undergo Hoffmanns bromamide degradation to amine on treatment with alkaline bromine
solution.
Reason: 2
o
-amide can not form isocynate, a key intermediate in the reaction.

A
37. Assertion: Phenol is brominated with Br
2
-H
2
O, even in absence of Lewis acid catalyst.
Reason: The HO-group in phenol is a strong activating group in electrophilic substitution reaction.

B
38. Assertion: Aliphatic amines do not forms diazonium salt as a stable product like aniline.
Reason: Benzene diazonium salt is stabilized by resonance.

A
39. Assertion: During Friedel Craft acylation of benzene using(CH
3
)
3
C-COCl/AlCl
3
, Some tertiary butyl benzene is also formed.
Reason: The acylium ion formed initially, decomposes partially in case where tertiary carbocation is formed.

A
40. Assertion: The equilibrium constant of the following process is greater than one.
O O
O OH

Reason: The enol is more stable than keto form due to conjugation and intramolecular H-bonding.

A

S CO 4 8 , I I
n d
7

Section-D
Comprehension Section

Comprehension-1:
Consider the following synthetic scheme to answer the next three questions:
C H
3
OC
2
H
5
O
CH
3
O
C
2
H
5
ONa
O
MeO
A
heat
B
NaBH
4
/H
2
O
C
H
+
heat
D
HO
/H
2
O

41. The structure of A and B respectively:
(a)
O
COOC
2
H
5
OMe
and
O
OMe
(b)
OMe
O
COOCH
3
OMe
O
and
(c)
OMe
O
COOC
2
H
5
O
and
OMe
O O
(d)
O
C H
3
O
C COOC
2
H
5
C
CH
3
O
C H
3
O
C CH
3
CH
and

C
42. If C is treated with excess of CH
3
COCl, what would be formed?
(a) (b)
(c) (d)
OCOCH
3
OMe
OCOCH
3
OMe
OCOCH
3
OCOCH
3
OMe
OCOCH
3
OCOCH
3

C

S CO 4 8 , I I
n d
8
43. Which of the following is the most likely structure of product D?
(a) (b) (c) (d)
OMe OMe OMe OMe

B
Passage-2
Consider the following cross aldol condensation reaction and the possible products:
O
O
X
Y
NaOH
O
O
O
O
Possible Enolates
OH
O O
OH
O
OH
O
OH
O
OH OH
O O
OH
O
OH
A
B
C
D
E F
G
H
(I) (II)
(III)
(IV)
+
H
2
O
+
+ +
Aldol Products

Answer the following questions based on the above information.

44. Which is the most stable enolate?
(a) I (b) II (c) III (d) IV

B
45. Which of the above enolate is formed most rapidly?
(a) I (b) II (c) III (d) IV

C
46. Nucleophilic addition of enolate on carbonyl compound gives A-H. Which of the following combination of enolate-
carbonyl compound and the resulting product is correctly matched?

(a) I + X A; II + X C and III + X D (b) II + X C; III + Y D and III + X E

(c) IV + Y F; III + Y H and IV + X G (d) I + Y E; II + Y D and III + X G

B

S CO 4 8 , I I
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9

Section-E
Single Integer Answer Type

47. If ethanedial (HOCCOH) is treated with excess of HCN(aq) followed by hydrolysis of product results in diacids. How many
different diacids would be formed?

3
48. An organic compound(X) has molecular formula C
7
H
6
O
2
and it does not effervesces with NaH. A on treatment with excess of
HBr(aq) gives Y(C
6
H
6
O
2
) and CH
2
Br
2
. Y forms a violet coloured solution with FeCl
3
. If X is treated with Br
2
/Fe, how many
different monobromination product would result?

2
49. An organic acid (X) has molecular formula C
8
H
16
O
2
. X on heating with NH
3
forms Y which on treatment with alkaline Br
2

forms Z. Z on treatment with HNO
2
followed by heating with H
2
SO
4
gives 2,4-dimethyl-2-pentene. How many different acids
(X) can give the indicated final product?

4
50. If CH
2
DCHO is treated with dilute alkaline solution, how many different aldols (excluding stereo-isomers) are expected? 4

S CO 4 8 , I I
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10
Answer Sheet
Name: _______________________________________________________________________
Batch: _______________________________________________________________________

1.
A B C D

18.
A B C D

35.
A B C D

2.
A B C D

19.
A B C D

36.
A B C D

3.
A B C D

20.
A B C D

37.
A B C D

4.
A B C D

21.
A B C D

38.
A B C D

5.
A B C D

22.
A B C D

39.
A B C D

6.
A B C D

23.
A B C D

40.
A B C D

7.
A B C D

24.
A B C D

41.
A B C D

8.
A B C D

25.
A B C D

42.
A B C D

9.
A B C D

26.
A B C D

43.
A B C D

10.
A B C D

27.
A B C D

44.
A B C D

11.
A B C D

28.
A B C D

45.
A B C D

12.
A B C D

29.
A B C D

46.
A B C D

13.
A B C D

30.
A B C D

14.
A B C D

31.
A B C D

15.
A B C D

32.
A B C D

16.
A B C D

33.
A B C D

17.
A B C D

34.
A B C D

50. 47.
48.
49.
50.

S CO 4 8 , I I
n d
11

Answer Test Series 4[+2] IIT-JEE 2010
Set
A AA A B C CC C
Set
A B C
Set

1.
D D B
21.
B D B
41.
C

2.
A C D
22.
A C C
42.
C

3.
B A B
23.
B B B
43.
B

4.
B C D
24.
D D C
44.
B

5.
A B A
25.
D A B
45.
C

6.
B B A
26.
B A B
46.
B

7.
C C D
27.
A D C
47.
3

8.
C B B
28.
D B A
48.
2

9.
C C C
29.
D D C
49.
4

10.
D B D
30.
D B D
50.
4

11.
C C D
31.
A C

12.
D D D
32.
A D

13.
B D B
33.
C D

14.
C B B
34.
A B

15.
C C A
35.
A B

16.
C A C
36.
A

17.
B B B
37.
B

18.
B B D
38.
A

19.
B D D
39.
A

20.
D D C
40.
A

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