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IIT-

IIT-JEE 2009

PART-I
SECTION-I
Single Correct Choice Type
This section contains 4 multiple choice questions. Each question has 4 choices (A), (B), (C) and (D) for its answer, out of which ONLY ONE is correct
1. The correct stability order of the following resonance structures is
+ − + − − + − +
H 2C = N = N H 2 C− N = N H 2 C− N ≡ N H 2 C− N = N
(I) (II) (III) (IV)

(A) (I) > (II) > (IV) > (III) (B) (I) > (III) > (II) > (IV) (C) (II) > (I) > (III) > (IV) (D) (III) > (I) > (IV) > (II)
+ − + − − + − +
Sol. (B) H 2C = N = N H 2 C− N = N H 2 C− N ≡ N H 2 C− N = N
(I) (II) (III) (IV)

octet complete octet incomplete octet complete octet incomplete


–ve charge on nitrogen –ve charge on nitrogen –ve charge on carbon –ve charge on carbon
2. In the following carbocation, H / CH 3 that is most likely to migrate to the positively charged carbon is

H H
1 + |2
|4 5
H 3 C — C — C — C — CH 3
| 3| |
HO H CH 3

(A) CH 3 at C − 4 (B) H at C − 4 (C) CH 3 at C − 2 (D) H at C − 2


Sol. (D)
H H H H
H H
1 + |2
|4 5 1 + | | 5 1
| | 5
1, 2 Hydride shift
H 3 C — C — C — C — CH 3   → H 3 C — C 2 — C 3 — C 4 — C H 3 H3 C— C 2 — C3 — C4 — C H3
| 3| |
| | | || | |
HO H CH3 H CH 3 H CH 3
HO: HO +
..

(More stable carbocation due to


+m effect of –OH group and +I and
hyperconjugative effect of −CH 3 group)
1
3. For a first order reaction A → P , the temperature (T) dependent rate constant (k) was found to follow the equation log k = −(2000) + 6.0 . The pre-
T
exponential factor A and the activation energy Ea , respectively, are

(A) 1.0 × 10 6 s −1 and 9.2 kJ mol −1 (B) 6.0 s −1 and 16.6 kJ mol −1

(C) 1.0 × 10 6 s −1 and 16.6 kJ mol −1 (D) 1.0 × 10 6 s −1 and 38.3 kJ mol −1

Sol. (D) From Arrhenius equation K = A e − Ea / RT


Ea
ln k = ln A −
RT
Ea
2.303 log K = 2.303 log A −
Rt
− Ea 1
log K = × + log A .....(i)
2.303 R T
1
log K = −(2000)
+6 .....(ii)
T
On comparing equation (i) and (ii)
− Ea
= −2000 .
2.303 R
Ea = 2.303 × 8.314 × 2000 = 38.29 kJ
and log A = 6 A = 10 6

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IIT-
IIT-JEE 2009
4. The spin only magnetic moment value (in Bohr magneton units) of Cr(CO)6 is
(A) 0 (B) 2.84 (C) 4.90 (D) 5.92
Sol. (A) The chromium is in zero oxidation state having configuration [ Ar] 3d 4 s . The CO is a strong field ligand so compels for the pairing of
18 5 1

electrons. Thus the complex has d 2 sp 3 hybridisation and is diamagnetic.

[Cr (CO)6 ]

Rearrangement d2sp3 hybridization

µ BM = n (n + 2) = 0 as there is no unpaired electrons.

SECTION – II
Multiple Correct Choice Type
This section contains 5 multiple choice questions. Each question has 4 choices (A), (B), (C) and (D) for its answer, out of which ONE OR MORE is/
are correct.

5. In the reaction , 2 X + B2 H 6 → [ BH 2 ( X ) 2 ]+ [ BH 4 ]− , the amine(s) X is (are)

(A) NH 3 (B) CH 3 NH 2 (C) (CH 3 ) 2 NH (D) (CH 3 )3 N

Sol. (A,B,C) Small amines such as NH 3 , CH 3 NH 2 and (CH 3 ) 2 NH give unsymmetrical cleavage of diborane according to following reaction.

B2 H 6 + 2 NH 3 → [ H 2 B ( NH 3 )2 ]+ [ BH 4 ]−

Large ammines, such as (CH 3 ) 3 N gives symmetrical cleavage of diborane according to following reaction.

B2 H 6 + 2 N (CH 3 ) 3 → 2H 3 B ←
 N (CH 3 ) 3

6. The nitrogen oxide(s) that contain(s) N − N bond(s) is (are)


(A) N 2O (B) N 2 O3 (C) N 2 O4 (D) N 2 O5
Sol. (A,B,C)
O O
1.126 Å 1.864 Å
1.186 Å
(A) N N   → O (B) N N
N 2O O
asymmetric form of N2O3

O O O O

(C) N N (D) N —O— N


O O O O
N 2O 4 N 2O 5

7. For the reduction of NO3− ion in an aqueous solution, E 0 is +0.96 V . Values of E 0 for some metal ions are given below

V 2 + (aq) + 2e − → V E 0 = −1.19 V

Fe 3 + (aq) + 3e − → Fe E 0 = −0.04 V

Au 3 + (aq) + 3e − → Au E 0 = +1.40 V

Hg 2 + (aq) + 2e − → Hg E 0 = +0.86 V

The pair(s) of metals that is(are) oxidized by NO3− in aqueous solution is(are)
(A) V and Hg (B) Hg and Fe (C) Fe and Au (D) Fe and V

(A,B,D) The species having less reduction potential with respect to NO 3 ( E 0 = 0.96 V ) will be oxidised by NO 3 .
− −
Sol.
These species are V , Fe, Hg .

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IIT-JEE 2009
8. The correct statement(s) about the following sugars X and Y is(are) CH2OH

O
CH2OH CH2OH H H H
O H H HO OH
O H HOH2C O
H H O
H H
O CH2OH
OH H H HO OH H OH H
HO HO H

H OH OH H H OH

X Y
(A) X is a reducing sugar and Y is a non-reducing sugar (B) X is a non-reducing sugar and Y is a reducing sugar
(C) The glucosidic linkages in X and Y are α and β , respectively (D) The glucosidic linkages in X and Y are β and α , respectively
Sol. (B,C) X has acetal linkage and Y has hemiacetal linkage. Carbohydrate with hemiacetal linkage are reducing sugars and carbohydrate with acetal
linkage are non reducing sugars.
X is α − anomer and Y is β − anomer of D (+) glucose.

9. Among the following, the state function(s) is(are)


(A) Internal energy (B) Irreversible expansion work (C) Reversible expansion work (D) Molar enthalpy
Sol. (A,D) State function are internal energy and molar enthalpy.
Work is path function whether it is reversible or irreversible.

SECTION – III
Matrix – Match Type
This section contains 2 questions. Each question contains statements given in two columns, which have to be matched. The statements in Column I
are labelled A, B, C and D, while the statements in Column II are labelled p, q, r, s and t. Any given statement in Column I can have correct
matching with ONE OR MORE statements(s) in Column II. The appropriate bubbles corresponding to the answers to these questions have to be
darkened as illustrated in the following example :
If the correct matches are A-p, s and t; B – q and r; C – p and q; and D- s and t; then the correct darkening of bubbles will look like the following.

p q r s t

A p q r s t

B p q r s t

C p q r s t

D p q r s t

10. Match each of the compounds given in Column I with the reaction(s), that they can undergo, given in Column II.
Column I Column II
Br
(A) (p) Nucleophilic substitution
O

OH
(B) (q) Elimination

CHO
(C) (r) Nucleophilic addition
OH

Br
(D) (s) Esterification with acetic anhydride
NO2
(t) Dehydrogenation

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IIT-JEE 2009
Sol. (A) p, q, t; (B) p, s, t; (C) r, s; (D) p

 Nu
Nu:
(p) +Br
O
Br
: B(− HBr )
(A) (p)
O O
Br
Pd − C(∆), − H2
(t)
O

HX (SN) X
(p) +H2O
OH
(B)

(CH3CO)2O O–C–CH3
(s)
O

Nu
Θ
N u : H⊕ OH
(r)

CHO OH
(C)
OH
CHO
(CH3CO)2O
(s)
O–C–CH3

O
Br Nu : Θ Nu
(D) (r) + Br:Θ
NO2

11. Match each of the reactions given in Column I with the corresponding product(s) given in Column II.
Column I Column II
(A) Cu + dil HNO3 (p) NO

(B) Cu + conc HNO3 (q) NO 2

(C) Zn + dil HNO3 (r) N 2O

(D) Zn + conc HNO 3 (s) Cu(NO3 ) 2

(t) Zn(NO3 ) 2
Sol. (A) p, s; (B) q, s; (C) r, t; (D) q, t
(A) 3Cu + 8 HNO3 (dilute HNO3 ) → 2 NO + Cu( NO3 )2 + 4 H 2 O

(B) Cu + 4 HNO3 (concentrated) → 2 NO2 + Cu( NO3 )2 + 2 H 2O

(C) 4 Zn + 10 HNO3 (dilute) → 4 Zn( NO3 )2 + N 2 O + 5 H 2O

(D) Zn + 4 HNO3 (concentrated) → Zn( NO3 )2 + 2 NO2 + 2H 2 O

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IIT-
IIT-JEE 2009
SECTION – IV
Integer Answer Type
This section contains 8 questions. The answer to each of the questions is a single digit integer, ranging from 0 to 9. The appropriate bubbles below the
respective question numbers in the ORS have to be darkened. For example, if the correct answers to question numbers X, Y, Z and W (say) are 6, 0, 9,
and 2, respectively, then the correct darkening of bubbles will look like the following :
X Y Z W
0 0 0 0
1 1 1 1
2 2 2 2
3 3 3 3
4 4 4 4
5 5 5 5
6 6 6 6
7 7 7 7
8 8 8 8
9 9 9 9

238 214
12. The total number of α and β particles emitted in the nuclear reaction 92 U → 82 Pb is

Sol. 238
92 U → 214
82 Pb + 6 (42 He) + 2 (−1 e 0 )

α = 6, β = 2
Total = 8 .
13. The number of water molecule(s) directly bonded to the metal centre in CuSO4 .5 H 2 O is

H H

O

H H H O O
Sol. (4) O Cu2+ :O O S

H H H O O
O

H H
14. The oxidation number of Mn in the product of alkaline oxidative fusion of MnO2 is

Sol. 2MnO2 + 4 KOH + O2  → 2 K 2 MnO4 + 2 H 2 O


fusion

2−
Let the oxidation state of Mn in MnO4 is x.

So, x + 4 (−2) = −2 or x = 6 .

15. The coordination number of Al in the crystalline state of AlCl 3 is


Sol. (6)
16. In a constant volume calorimeter, 3.5 g of a gas with molecular weight 28 was burnt in excess oxygen at 298.0 K . The temperature of the calorimeter

was found to increase from 298.0 K to 298.45 K due to the combustion process. Given that the heat capacity of the calorimeter is 2.5 kJ K −1 , the
numerical value for the enthalpy of combustion of the gas in kJ mol −1 is

3.5
Sol. n=
28
∆T = T2 − T1 = 298.45 − 298 = 0.45

CV = 2.5 kJ k −1 = 2500 JK −1

CP = CV + R = 2500 + 8.314 = 2508.314 JK −1

QP = CP ∆T = 1128.74 J

QP 1128.74
∆H = = ⇒ 9030 J mol −1 = 9.030 KJ mol −1 = 9 KJ mol −1 .
n 3.5 / 28

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IIT-JEE 2009
17. The total number of cyclic structural as well as stereo isomers possible for a compound with the molecular formula C 5 H 10 is
Sol. (7)

H3 C CH3 H3 C CH3 H3 C CH3


(1) (2) (3) (4) (5) (6) (7)
(cis, meso) Trans (±)

18. The dissociation constant of a substituted benzoic acid at 25 o C is 1.0 × 10 −4 . The pH of a 0.01M solution of its sodium salt is

Sol. Given K a = 10 −4

pK a = 4

C = 0.01 M

1 1 1 1
pH = 7 + pK a + log C = 7 + (4) + (−2) = 8 .
2 2 2 2

19. At 400 K , the root mean square (rms) speed of a gas X (molecular weight = 40) is equal to the most probable speed of gas Y at 60 K. The molecular
weight of the gas Y is
Sol. Vrms = Vmp

3 RT 2RT
=
MX MY

3 R × 400 2R × 60
=
40 MY

MY = 4 .

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