Class11 12 Nsec Incho

PATHFINDER-2013
FIITJEE
ALL INDIA SCREENING TEST
(NSEC + INCho)
Time: 3 Hours
Maximum Marks: 230.
A. General:
1. This Question Paper contains 2 Parts. Part-A & Part-B.
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separately for Part-A.
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B. Filling the top-half of the ORS:

7. Write your Name & Registration No. in the space provided in the bottom of this booklet.
8. Darken the appropriate bubbles below your Registration No. with HB Pencil.
C. Question paper format and Marking scheme:

9. The question paper consists of 2 Parts.
(i) Part-A (01 to 60) contains 60 multiple choice questions which have only one correct answer.
Each question carries +3 marks for correct answer and 1 mark for wrong answer.
(ii) Part-B (1 to 3) consists of 3 Subjective Questions each question containing sub parts with
marks indicated making up total of 50 Marks for 3 questions.
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P-AIST-2013-NSEC+INCho-SP-2
PART A
1.
When NH4Cl is dissolved in H2O, the temperature of H2O decreases it means:

(where, Hs = enthalpy of solution, Hi = enthalpy of ionisation and Hh = enthalpy of hydration of
ions)
(B) Hs = ve, Hi < Hh
(A) Hs = +ve, Hi < Hh
(D) Hs = +ve, Hi > Hh
(C) Hs = ve, Hi > Hh
2.
An electron in an atom jumps in such a way that its kinetic energy changes from x to
change in potential energy will be:
3
(A) + x
2
3
(C) + x
4
3.
x
, the
4
3
x
8
3
(D) x
4
(B)
The most reactive among the following for electrophilic substitution reaction is:
F
(A)
(B)
Cl
(C)
Br
(D)
4.
The product which is not formed during Kolbes electrolysis of propanoic acid.
(A) CH3CH2CH2CH2CH3
(B) CH3CH2COOCH2CH3
(D) None of the above
(C) CH2 = CH2
5.
2-halohexane is treated with CH3ONa and CH3OH. The highest ratio of amount of 1-hexene to 2hexene will be obtained, if halogen is
(A) F
(B) Cl
(C) Br
(D) I
Rough work
6.
Match the following:

Reaction
(a)
Borax
(i)
Product
Na[B(OH)4] + H3BO3
(b)
Borax + NH4 Cl
(ii)
NaBO2 + B2O3
(c)
HCl
Borax
(iii)
BN
(d)
Borax + H2O
(iv)
H3BO3
(A)
(B)
(C)
(D)
a
(ii)
(iii)
(ii)
(ii)
b
(iii)
(ii)
(iii)
(i)
c
(i)
(iv)
(iv)
(iv)
d
(iv)
(i)
(i)
(iii)
7.
The correct set of all the four quantum numbers for the 21st electron in scandium (Sc = 21) is:
1
1
(B) n = 3, l = 2, m = - 2, S = +
(A) n = 3, l = 1, m = - 2, S = +
2
2
1
1
(C) n = 4, l = 0, m = - 1, S = +
(D) n = 4, l = 0, m = - 2, S =
2
2
8.
Identify the incorrect statement of the following:

(A) Carbondioxide is isostructural with laughing gas.
(B) Borazole is isostructural with benzene.
(C) Azide ion is isostructural with polyiodide ion (I3 )
(D) Trimethyl amine is isostructural with trisilylamine.
9.
In which of the following reactions, hybridization of underlined atoms do not undergo any change?
3+
Fe ( CN)6
(A) Fe (H2 O )6 + 6CN
NO2+ + NO3
(C) N2 O5
10.
(B) LiH + AlH3 LiAlH4

(D) 2NH3 + H2 SO4
(NH4 )2 SO 4
The total volume of 0.1 M KMnO4 solution that are needed to oxidize 100 mg each of ferrous
oxalate and ferrous sulphate in a mixture in acidic medium is:
(A) 4.16 ml
(B) 1.32 ml
(C) 5.48 ml
(D) 2.64 ml
Rough work
11.
Identify the correct statement among the following:

(A) The number of isomers of compound with molecular formula C4H6 are 6
(B) Total number of aliphatic ethers corresponding to the molecular formula C5H12O are 6
(C) Total number of optically active isomers of HOOC-CH(OH) CH (OH) COOCH3; are 4
(D) All of the above
12.
Which of the following carbananion is most stable?

(A)
(B)
CH
2
(C)
(D)
CH3
HC
CH2
HC
CH3
NO2
13.
The temperature at which the reaction, Ag2 O ( s ) 2Ag ( s ) +
1
O2 ( g) is at equilibrium is ,
2
given H = 30.5 kJmol1 and S = 0.066 kJK 1mol1

(A) 462.12 K
(B) 362.12 K
(C) 262.12 K
(D) 562.12 K
14.
15.
Which of the following exist as dimer?

(A) CH3Li
(C) Al(CH3)3
(B) Si(CH3)4
(D) Be(CH3)2
Solubility of calcium phosphate (molecualr mass M) in m g per 100 mL at 25oC, its solubility
product at 25oC will be approximately.
m
(A) 107
M
m
(B) 107
M
m
(C) 105
M
m
(D) 103
M
Rough work
16.
1 M solution of CH3COOH should be diluted to ...................... times so that pH is doubled.

(A) four times
(B) 5.55 104 times
6
(C) 5.55 10 times
(D) 102 times
17.
The dissociation constants of HA and HB are 6 104 and 2.0 104 respectively. The pH of a
solution which is mixture of 0.5 M of HA and 0.5 M of HB is
(A) 2.00
(B) 1.70
(C) 2.30
(D) 1.90
18.
pKb of NH3 is 4.74 and pKb of A, B and C are 4, 5 and 6 respectively. Aqueous solution of 0.01
M has pH in the incrasing order.
(A) NH4A < NH4B < MH4C
(B) NH4C < NH4B < NH4A
(C) NH4C < NH4A < NH4B
(D) All have equal pH, being salt of weak acid and weak base
19.
Which of the following can be separated by H2S in dil HCl?

(ii) Al3+Hg2+
(i) Bi3+Mn2+
2+
2+
(iii) Zn Cu
(iv) Ni2+Cu2+
(A) (i) and (ii)
(B) (i) and (iii)
(C) (i), (ii), (iii)
(D) All
20.
+
o
-19
ZZZ
X
Kc for the reaction [Ag(CN)2]-1 YZZ
Z Ag + 2CN , the equilibrium constant at 25 C is 4 10 ,
then the silver ion concentration in the solution which was originally 0.1 M in KCN and 0.03 M in
AgNO3 is
(B) 7.5 10-18
(A) 7.5 1018
19
(C) 7.5 10
(D) 7.5 10-19
21.
Important ore of lead is:

(A) bauxite
(C) cinnabar
22.
(B) galena
(D) malachite
The ratio of the radius difference between 4th and 3rd orbit of H-atom and that of Li2+ ion is
(A) 1 : 1
(B) 3 : 1
(C) 3 : 4
(D) 1 : 3
Rough work
23.
For the reaction

FeS2 + KMnO4 + H+
Fe3 + + H2SO4 + Mn2+ + H2O , if the molar mass of FeS2 is M, then
equivalent mass of FeS2 would be equal to
(A) M
(B) M/10
(C) M/11
(D) M/15
24.
Borane have general formula

(A) BnHn+4
(C) BnH2n+2
(B) BnHn+6
(D) Both (A) and (B)
25.
NaOCl on heating with NH3 at high temperature gives:

(A) H2N NH2(hydrazine)
(B) Dinitrogen (N2)
(C) H2(Dihydrogen)
(D) Sodiumamide(NaNH2)
26.
S2 in vapour phase is
(A) paramagnetic
(C) ferromagnetic
(B) diamagnetic
(D) doesnt exist
27.
Which of the following statements is correct?

(A) B2H6 reacts with excess of NH3 at high temperature to form an ionic substance
(B) B2H6 reacts with excess of NH3 at low temperature to form a white slippery solid
(C) Boron nitride has layer structure
(D) orthoboric acid is monoprotic acid
28.
CH2 = CHCH2Cl and CH3CH = CH2Cl can be distinguished by the reaction with
(B) K2Cr2O7/H2SO4
(A) Br2 in CCl4
(C) AgNO3
(D) NaOI
29.
A sample of peanut oil weighing 1.576 g is added to 25 ml of 0.421 M KOH. After saponification is
complete, 8.46 ml of 0.273 M H2SO4 is needed to neutralize excess of KOH. The saponification
number of peanut oil is (saponification number is defined as the milligrams of KOH consumed by
1 g of oil)
(A) 209.6
(B) 108.9
(C) 98.9
(D) 218 .9
30.
At which of the following four conditions, the density of nitrogen will be the largest?
(A) STP
(B) 273 K and 2 atm
(C) 546 K and 1 atm
(D) 546 K and 2 atm
Rough work
31.
Cl2 gas has been introduced in an 8 litre cubical container at pressure 5 atm and 300 K
temperature. The following equilibrium has been achieved.
ZZZ
X
Al(s) + 3/2Cl2(g) YZZ
Z AlCl3(s)
If the thickness of inner side of walls has been decreased by 0.04 mm at equilibrium, then find out
Kp for the reaction ( Al = 1.13 g/cc)
(B) (2.7)3/2
(A) (2.7)+3/2
+3/2
(C) (5.4)
(D) (5.4)3/2
32.
A sample of hard water contains 0.005 mole of calcium chloride per litre. What is the minimum
concentration of sodium sulphate which must be added for removing the Ca2+ ions from this water
sample? (Ksp(CaSO4) = 2.4105)
(A) 4.8102
(B) 4.8103
2
(D) 2.4103
(C) 2.410
33.
ZZZ
X
N2 + 3H2 YZZ
Z 2NH3 + heat. The activation energy for the forward as well as backward reaction is
decreased by 100 J, then the equilibrium amount of NH3 will
(A) increase
(B) decrease
(C) remain constant
(D) cannot be predicted
34.
The coefficient of S in the balanced reaction is

As2S5 + H2 Cr2 O7 H3 AsO4 + S + Cr 3 +
(A) 5
(C) 15
(B) 10
(D) 1
35.
The pH of a saturated solution of M(OH)2 is 10. The Ksp value at this temperature is
(B) 5 1010
(A) 5 1013
8
(C) 5 10
36.
Which of the following statement is not correct?

(A) Hybridization is the mixing of atomic orbitals prior to their combining into molecular orbitals.
(B) sp2 hybrid orbitals are formed from two p-atomic orbitals and one s-atomic orbital.
(C) dsp3 hybrid orbitals are all at 90o to one another.
(D) d2sp3 hybrid orbitals are directed towards the corner of regular octahedral.
Rough work
37.
Which of the following statement is/are not true for bond ?

1. It is formed by the overlapping of p p or p d orbitals.
2. It is stronger than sigma bond.
3. It is formed when bond already exists.
4. It is resulted from sideways overlapping of orbitals.
(A) 1, 2, 3, 4
(B) 2, 3 and 4
(C) 2 and 4
(D) 1, 2 and 4
38.
A sample of water from newly dug well read pH = 7 in the field study on the night of
31st Dec. 2005 in Shimla. The sample was
(A) basic
(B) acidic
(C) neutral
(D) cannot be predicted
39.
The circumference of the 4th orbit of hydrogen is 5.32 nm. The wavelength of electron revolving in
the first Bohr orbit will be
(A) 0.133 nm
(B) 1.33 nm
(C) 4.32 nm
40.
In which reaction, product formation occurs by Saytzeff rule?
OH
Br
(1)
CH3
ONa ,
(2)
H3C
conc. H2SO4
H 2C
CH3
CH3
Br
(3)
CH3
Cl
aq. KOH/
CH3
Ph
CH3
(4)
Cl2 / h
F 3C
CH3
Cl
Select the correct alternative from the codes given below:

Codes:
(A) 1, 2 and 3
(B) 2 and 3
(C) 1, 2 and 4
(D) 2, 3 and 4
41.
What will be the molar solubility of molar solution of AgCl at 25oC if specific conductivity of
saturated AgCl solution is 2.3 106 S.cm1 at 25oC and molar conductivities of
Ag+ and Cl at infinite dilution are 61.9 and 76.3 Scm2mol1 respectively?
(B) 1.66 105 M
(A) 2.382 103 M
8
(C) 5 10 M
(D) 7.2 106 M
Rough work
42.
Following reaction occurs at 25oC,

2
o
ZZZ
X
2NO(g)(1 105 atm) + Cl2 (g)(1 10 2 atm) YZZ
Z 2NOCl(1 10 atm); the value of G is
(A) 45.65 kJ
(B) 28.53 kJ
(C) 22.82 kJ
(D) 57.06 kJ
43.
The approximate heat necessary to raise the temperature of 18.4 gm of ethyl alcohol from 45oC
to 55oC at 1 atm pressure (Cp = 26.8 cal/mole) is
(A) 53.6 cal
(B) 107.2 cal
(C) 214.4 cal
(D) 536 cal
44.
Find H at 358 K for the reaction,

Fe2 O3 (s) + 3H2 (g) 2Fe(s) + 3H2 O(A )
Given that, H298 = 33.29 kJ / mole and Cp for Fe2O3(s), Fe(s), H2 O(A ) and H2 (g) are 103.8, 25.1,
75.3 and 28.8 J/K mole.
(A) 85.9 kJ/mole
(B) 28.136 kJ/mole
(C) +28.136 kJ/mole
(D) 85.9 J/mole
45.
Give the correct increasing order of acid strength.

OH
OH
OH
OH
(I)
OMe
(II)
NO2
(III)
Cl
(IV)
(A) III > IV > I > II

(C) IV > I > II > III
(B) IV > III > I > II

(D) I > II > III > IV
Rough work
46.
In the following reaction

BH
CH COOH
3
3
CH3 CH = CH2
A
B
A and B are,
H3C
H3C
B ,
(A)
(B)
H3C
H3C
CH2
H3C
(C)
CH3
CH2
CH2
CH2
B ,
H3C
47.
O
H3C
B ,
CH3
H3C
CH3
For the following compounds
N
(I)
NH2
CH3
N
(II)
N
(III)
the correct order of basic strength

(A) IV < III < II < I
(C) II < IV < I < III
48.
CH3
H3C
(D)
H3C
B ,
CN
N
(IV)
(B) IV < I < III < II

(D) I < II < III < IV
Borazene, B3N3H6, is isoelectronic and isostructural with benzene. Which of the following
statement(s) is/are true about borazene?
(i) Borazene is aromatic.
(ii) There are four isotopic disubstituted borazene molecules, B3N3H4X2.
(iii) Borazene is more reactive towards addition reactions than benzene.
(A) Only (i)
(B) (i) and (ii)
(C) (i) and (iii)
(D) (i), (ii) and (iii)
Rough work
CH3
49.
Cl
HCl
A. A is
R O
H3C
(A)
2 2
CH3
H5 C 2
CH3 Cl
H3C
and formed through carbocation formation

CH3 Cl
CH3 Cl
(B)
C2H5
Cl
H3C
(C)
and formed through carbocation formation

CH3 H
CH3 Cl
C2H5
CH3 Cl
CH3 Cl
C2H 5
H3C
(D)
and formed through carbon free radical

Cl
H3C
and formed through carbon free radical

CH3 H
C2H 5
50.
In Castners process some sodium is lost because

(A) It reacts with dissolved O2 in molten NaOH
(B) Due to its high reactivity it attacks other substance present in the system
(C) At high temperature some of it vapourises
(D) All of the above
51.
One mole of a hydrocarbon (A), reacts with one mole of bromine in (CCl4), giving a dibromo
compound (C5H10Br2). Substance (A) on treatment with cold dil. Alkaline KMnO4 solution forms a
compound (C5H12O2). On ozonlysis (A) gives equimolar quantities of propanone and ethanol.
Hence compound (A) is
(A) 2-butene
(B) 2-methyl but-2-ene
(C) 1-methyl cyclobutene
(D) 2-methyl but-1-ene
52.
For the equilibrium at 298 K

+
ZZZ
X
2H2 O YZZ
Z H3 O + OH
G is approximately:
(A) 100 KJ
(C) 80 KJ
(B) 80 KJ
(D) 100 KJ
Rough work
53.
NCl3 on hydrolysis will give NH3 and HOCl but PCl3 on hydrolysis gives H3PO3 & HCl because
(A) N is more electronegative than phosphorus
(B) size of P is larger than nitrogen
(C) P is having vacant d-orbital
(D) A & C are correct
54.
Calculate resonance energy of N2O from the following data:

H0f (N2 O ) = 82KJ mol1
BE of N N = 946 KJ mol1
BE of O = O = 498 KJ mol1
(A) 68 KJ mol1
(C) 88 KJ mol1
55.
BE of N = N = 418 KJ mol1
BE of N = O = 607 KJ mol1
(B) 42 KJ mol1
(D) 56 KJ mol1
Consider the following single step conversion:

CH3
OH
( )
Re agent x
COOH
OH
The reagent (X) in the above reaction is

(A) MnO2
(C) KMnO4/OH
56.
(B) PbO2
(D) K2Cr2O7/H+
The standard reduction potential values of three metallic cations x, y, z are 0.52, 3.03 and 1.18
V respectively. The order of reducing power of the corresponding metal is
(A) y > z > x
(B) x > y > z
(C) z > y > x
(D) z > x > y
Rough work
57.
H
BH3 .THF
A, A is
H O / OH
2
O
H
(A)
(B)
CH3
(C)
58.
OH
(D)
In the following there are three carbon-oxygen bonds denoted by x, y and z:

O
x
H3C
CH3
Their lengths are in order

(A) x = y = z
(C) x < y = z
(B) x < y < z

(D) y < x < z
Rough work
59.
HO
CH3
The correct IUPAC name of the above compound:

(A) 4-(3-methyl-5-hydroxylphenyl)-3-methylpent-2-enal
(B) 4-(3-hydroxy-5-methylphenyl)-3-methylpent-2-enal
(C) 4-(3-methylphenol)-pent-2-enal
(D) 4-(3-hydroxy-5-methylphenyl)-3,4-dimethylbut-2-enal
60.
When acetylene is passed through conc. solution of Cu2Cl2 and ammonium chloride containing
some dil HCl and the substance formed reacts with dil HCl at 160C, if forms another substance
which then polymerizes. The polymer formed is
(A) Benzene
(B) Polyisoprene
(C) Neoprene
(D) PMMA
Rough work
PART B
Problem 1:
[16 marks]
Amount of 50 g of a 4 % sodium hydroxide solution and 50 g of a 1.825 % solution of hydrochloric acid

were mixed in a heat insulated vessel at a temperature of 20 C. The temperature of the solution obtained
in this way increased to 23.4 C. Then 70 g of a 3.5 % solution of sulphuric acid at a temperature of 20 C
were added to the above solution.
1.1
Calculate the final temperature of the resulting solution.
[1/2+1/2 +1/2+1 marks]
1.2
Determine the amount of a dry residue that remains after evaporation of the solution.
In calculating the first problem use the heat capacity value c = 4.19 J g1 K1.
Relative atomic masses:
Ar(H) = 1; Ar(O) = 16; Ar(Na)= 23; Ar(S) = 32; Ar(Cl) = 35.5.
[2 marks]
1.3
The gas escaping from a blast furnace has the following composition:
12.0 volume % of CO2 28.0 volume % of CO
0.6 volume % of CH4
3.0 volume % of H2
0.2 volume % of C2H4 56.2 volume % of N2
(i) Calculate the theoretical consumption of air (in m3) which is necessary for a total combustion
of 200 m3 of the above gas if both the gas and air are measured at the same temperature.
(Oxygen content in the air is about 20 % by volume).
[2 marks]
(ii) Determine the composition of combustion products if the gas is burned in a

20 % excess of air.
[3 marks]
1.4
A mixture of two solid elements with a mass of 1.52 g was treated with an excess of hydrochloric acid. A
volume of 0.896 dm3 of a gas was liberated in this process and 0.56 g of a residue remained which was
undissolved in the excess of the acid.
In another experiment, 1.52 g of the same mixture were allowed to react with an excess of a 10 % sodium
hydroxide solution. In this case 0.896 dm3 of a gas were also evolved but
0.96 g of an undissolved residue remained.
In the third experiment, 1.52 g of the initial mixture were heated to a high temperature without access of
the air. In this way a compound was formed which was totally soluble in hydrochloric acid and 0.448 dm3
of an unknown gas were released. All the gas obtained was introduced into a one litre closed vessel filled
with oxygen. After the reaction of the unknown gas with oxygen the pressure in the vessel decreased by
approximately ten times (T = const).
Write chemical equations for the above reactions and prove their correctness by calculations. In solving
the problem consider that the volumes of gases were measured at STP and round up the relative atomic
masses to whole numbers.
[1+1+1+1/2+1/2 marks]
1.5
(i) A mixture of metallic iron with freshly prepared iron (II) and iron (III) oxides was heated in a closed
vessel in the atmosphere of hydrogen. An amount of 4.72 g of the mixture when reacted, yields 3.92
g of iron and 0.90 g of water.
When the same amount of the mixture was allowed to react with an excess of a copper(II) sulphate
solution, 4.96 g of a solid mixture were obtained.
Calculate the amount of 7.3 % hydrochloric acid ( = 1.03 g cm-3) which is needed for a total
dissolution of 4.72 g of the starting mixture.
[2 marks]
(ii) What volume of a gas at STP is released?

Relative atomic masses:
Ar(O) = 16; Ar(S) = 32; Ar(Cl) = 35.5; Ar(Fe) = 56; Ar(Cu) = 64
[1/2 mark]
Problem 2:
[16 marks]
The sample A participates in the transformations in scheme 1. Only the products containing A are shown
in the scheme 1.
Scheme 1:
H2O
KOH
electrolysis
C
( 3) D
( 4) E
( 5) F
( 2)
O 2 + catalyst
O2
KOH
A
D
A
(1) B
( 6) G
( 7 ) H
(8) A + B + E
(9)
H 2 with heating
KOH
A
D
I
K
A+I+E
(10 ) J
(11)
(12)
(a) Substance A is a solid and is insoluble in water.

(b) Substances B and I are gases soluble in water.
(c) Substances E, F, J and K are solid and soluble in water.
(d) Aqueous solutions of B, G, H, I, J and K react with F, the products in all cases being E and D.
(e) The following transformations occur during the interaction with an aqueous solution
of iodine:
( )
( )
20
E ; H
A ; K
B
D ; G
L ; I
( 22) A ; J
( 23)
( 24 ) A
19
21
Write the chemical equations for the following interactions and balance them.
2.1
A B
[1 mark]
2.2
B C
[1 mark)
2.3
C D
[1 mark]
2.4
D E
[1 mark]
2.5
E F
[2 marks]
2.6
B G
[1 mark]
2.7
G H
[1 mark]
2.8
H A + B + E
[2 marks]
2.9
A I
[1 mark)
2.10
I J
[1 mark]
2.11
J K
[2 marks]
2.12
K A + I + E
[2 marks]
Problem 3:
[18 Marks]
A.
Structure Elucidation of Organic Compound
3.1
Compound A (C9H10O) shows a strong IR absorption at 1690 cm1). It shows the following signals
in its 1H NMR: 1.25 (3H, triplet), 3.0 (2H, quartet), 7.5 (3H, multiplet) and 8.0 (2H, multiplet).
A on oxidation with acidic potassium permanganate gives benzoic acid.
[Refer to the Table 1 and Table 2 give at the end of the problem]
(i) From the IR spectrum the compound A is expected to have functional group/s.
[1 mark]
(ii) The structure of A.
[3 marks)
+
Br2 / H
A
3.2
( C9H9BrO )
NaBH4
( C9H11BrO )
(i) Draw the structures of C and D.
[2 marks]
(ii) Draw the Fischer projection formulae of the isomers of D.
3.3
[2 marks]
Compound B, isomeric with A shows a strong IR absorption at 1730 cm1 and a medium peak at
2700 cm1. It shows the following signals in its 1H NMR spectrum: 2.7 (2H, triplet), 2.95 (2H,
triplet), 7.3 (5H, multiplet) and 9.7 (1H, singlet).
[Refer to the Table 1 and Table 2 give at the end of the problem]
(i) From the IR spectrum, the compound B is expected to have functional group/s.
[1 mark]
(ii) The structure of B.
[3 marks]
B.
Organic Reactions, Mechanisms and Stereochemistry
3.4
The reaction of cyclopentanol with sodium metal gives product A. A reacts with bromoethane to
give B.
(i) Identify A and B.
B
[2 marks]
(ii) Bromocyclopentane, on heating with sodium ethoxide, gives C. Identify C.
C
[1 mark]
(iii) In the above reaction (ii), ethoxide functions as:

(a) Electrophile
(b) Nucleophile
(c) Base
(d) Lewis acid
[1 mark]
When C is reacted with DBr (in dark), a mixture of products is obtained.

(iv) Draw the structures of the products.
[2 marks]
Table 1:
Some Characteristic Proton Chemical Shifts

Types of Proton
p,s,t-C-H
C = C-H
C = C-H
Ar H
Ar C H
OCH
O=CCH
ROOC C H
O=CH
R COOH
Table 1:
Chemical shift, (ppm)

0.9-1.5
4.6-5.9
2.0-2.3
6.0-8.5
2.2-3.0
3.3-4.0
2.0-2.7
2.0-2.6
9.0-10.0
610-12
Some Characteristic Infrared Absorption Frequencies

Compound Type
Alkanes
CH
Alkenes
CH
Aromatic
CH
Olefin
C=C
Alkyne C C
CO
C=O
OH
CN
Frequency Range (cm1)

2850 - 2960
1350 1470
3020 3080
675 1000
3000 3100
675 870
1640 1680
2100 2260
1080 1300
1650 1800
3200 3600
2210 - 2260
PATHFINDER-2013
FIITJEE
ALL INDIA SCREENING TEST
(NSEC + INCho)
ANSWERS, HINTS & SOLUTIONS
PART- A
1.
5.
9.
13.
17.
21.
25.
29.
33.
37.
41.
45.
49.
53.
57.
D
A
D
A
B
B
B
A
C
C
B
A
A
D
A
2.
6.
10.
14.
18.
22.
26.
30.
34.
38.
42.
46.
50.
54.
58.
A
C
C
C
B
B
A
B
C
B
A
C
A
C
B
3.
7.
11.
15.
19.
23.
27.
31.
35.
39.
43.
47.
51.
55.
59.
B
B
D
B
D
D
C
B
A
D
B
B
B
B
B
4.
8.
12.
16.
20.
24.
28.
32.
36.
40.
44.
48.
52.
56.
60.
D
D
D
B
B
D
C
B
C
B
B
D
C
A
C
HINTS & SOLUTIONS

PART- A
2x
2x + 8x 3
( 2x ) =
= x
4
4
2
2.
Change in P.E. = =
3.
F has dominating +M effect.
5.
F being the worst leaving group among halogens forms Hoffmann product.
7.
21st electron in Sc is present in 3dxy orbital. Hence, (B) is correct answer.
8.
(A) O = C = O & N N O , both are linear.

H
(b)
H
B
N
Benzene
H
Borazole
Hence, both are isostructural.

(C) Azide ion (N3 ) is linear (sp-hybridisation) while (I3 ) ion is also linear (AX2E3) geometry.
Hence, isostructural.
(D) Trimethylamine is pyramidal trisilyl while amine is triangular planar due to p d bonding
latter.
sp3
sp2
H3C
CH3
Pyramidal
H 3Si
CH3
SiH 3
SiH 3
Triangularplanar
sp2
sp d
(A) Fe (H2O )6
3 2
9.
3+
d sp
+ 6CN
Fe ( CN)6
sp3
(B) LiH + AlH3

LiAlH4
sp2
sp
sp2
(C) N2 O5
NO2+ + NO3
sp3
sp3
(D) 2NH3 + H2 SO4
NH4 SO4
2
Hence, (D) is the correct answer.
10.
Total meq. of KMnO4 = Total meq. of FeC2O4 + Total meq. of FeSO4

100 100
(0.1 5) V =
+
144 152
3
1
V = 5.48 ml.
Hence, (C) is the correct answer.
11.
(A) C C C;
CC CC
(B) C O C C C C;
C CO C C C;
C O C C C; C O C C C
C O C C;
C C O C C
(C)
H
HO
OH
HO
H
COOCH3
OH
HO
OH
OH
HO
COOCH3
12.
Increasing order of stability is

(C)<(A)<(B)<(D)
13.
G = H T S
At equilibrium G = 0
H = T S
30.5
H
T=
=
= 462.12 K
S 0.066
14.
AlCH3 is electron deficient, therefore it exist as dimer.

H
H
H
H3C
C
CH3
Al
Al
CH3
C
H3C
H
H
H
15.
K sp( Ca
10 m
= 108 S5 = 108
3 (PO4 )2 )
M
As, S =
16.
COOCH3
COOCH3
10 m
molL1
M
5
COOH
COOH
COOH
COOH
10 m
7 m
= 108
= 10 M approximately
3 (PO4 )2 )
M
K sp( Ca
pH = [pKa logC] = [pKa log1] =
pK a
2
pK a
= pK a
2
pH = pKa = [pKa logC]
pH' = 2 pH = 2
pKa = logC
logKa = logC
C = Ka = 1.8 105 M
1
Dilution = = 5.55 10 4 times
C
17.
H+ = K a1 C1 + K a2 C2 = ( 6 0.5 + 2 0.5 ) 10 4 = 2 10 2 M
pH = log(2 102) = log2 log102 = 0.3010 + 2.00 = 1.70
18.
Salts (NH4A, NH4B, NH4C) are of weak acid and weak base.
pK a pK b
pH = 7 +
2
2
Thus, greater the value of pKa of acid, greater the pH.
pKb (A, B, C): A < B < C
4
5
6
pKa (HA, HB, HC): HC < HB < HA
8
9
10
Thus pH (NH4C< NH4B < NH4A)
Hence (B) is the correct option.
Solution Bi3+ will form black precipitate where as Mn2+ does not in acidic medium due to higher
Ksp value.
Hg2+ gets precipitate as HgS but Al3+ does not.
Cu2+ gets precipitated as CuS(black) whereas Zn2+ gets precipitated but Ni2+ does not.
19.
20.
Kc = 4 10-19
ZZZ
X
Ag+ + 2CN YZZ
Z Ag ( CN)2
0.03 0.1
0
0.03
1
ZZZ
X
Ag ( CN) YZZ
Z Ag + 2CN
2
0.3
0
0.04
0.03 x
x
0.04 + 2x
t=0
Kc =
x ( 0.04 + 2x )
0.03 x
0.04 + 2x 0.04
0.03 x 0.03
Kc =
x. ( 0.04 )
= 4 1019
0.03
x = 7.5 10-18
= 4 1019
21.
Important ore of lead is galena (PbS).
22.
rn
n2
Z
42
32
, r3
= 16 9 = 7
1
1
16 9 7
r4 r3 for Li
=
3 3 3
for H, r4
7
=3
7/3
Ions = 3 : 1
So, ratio
23.
FeS2 + KMnO4 + H+
Fe3 + + H2SO4 + Mn2+ + H2O
FeS2
Fe3 +
Change of oxidation state of Fe is +1
FeS22 H2 SO4
1 2
25.
62
= 2
12
Change is 14
Total change 14 + 1 = 15,
n-factor = 15
Eq. wt. of FeS2 is M/15
2NaOCl + 2NH3 N2 + 3H2O + NaCl
28.
CH2 = CHCH2Cl reacts with AgNO3 form stable allylic carbocation and ppt. of AgCl but CH3CH =
CH2Cl form unstable vinyl carbocation so, reaction cannt occur in 2nd case.
29.
Equivalents of KOH used by oil = [25 0.421 8.46 0.273 2 ]103

Moles of KOH used = 5.90 103
Mass of KOH used in milligrams = 5.90 103 56 1000 = 330.40
330.40
Saponification number =
= 209.64
1.576
30.
Density of a gas is given =
PM
P
. Obviously, the choice that has greater
would have greater
RT
T
density.
(B)
31.
58
= 1.63
0.082 300
Mass of Al(s) = 0.05101(20206)1.13 = 13.56 gm
So, mass Al(s) dissociated = 0.5 moles
So, equilibrium established
ZZZ
X
Al(s) + 3/2 Cl2(g) YZZ
Z AlCl3(s)
nCl =
2
1.63
3
0.5
2
( )
So, Kp = pCl
32.
3 / 2
0.5
0.88 0.082 300
=
3 / 2
= (2.7)3/2
[Ca2+] = [CaCl2] = 0.005 (N)

K sp
= Ca2+ SO24
CaSO4
( )
2.40 10 5 = 0.005 SO24
2.4 105
SO24 =
(M) = 4.8103
5 103
35.
M(OH)2 M2+ + 2OH
pH = 14 pOH
10 = 14 pOH
pOH = 14 10 = 4
log OH = 4;
[OH] = 104 M
2
K sp = M OH
104
4 2
=
[10 ]
2
= 5 1013
38.
The value of K decreases with decreases in temperature.

K w < 1014 (at temperature > 25oC)
H+ < 107
For neutral water, pH = log H+
pH > 7
So, pH 7 indicated must be acidic.
39.
2r = n
Circumference = 2r = 5.32 = 4 4
5.32
= 1.33
4
Now, 2r1 = 1, also r4 = r1 42
Hence, (D).
4 =
40.
(1) proceeds through E2 path while (2) and (3) proceeds through E1 path and (4) proceeds
through E1CB path.
Hence, only 2 and 3 takes place through Saytzeff rule.
41.
S=
=
K 1000
oAgCl
2.3 10 6 1000
(61.9 + 76.3)
= 1.66 105 M
42.
K eq =
2
PNOCl
= 108
2
PNO
PCl2
G = RT An K eq = 2.303 8.314 298 8 = 45.65 kJ
18.4
= 0.4
46
Q = nCp T = 0.4 26.8 10 = 107.2 cal / mole
43.
n=
44.
Cp = 2 25.1 + 3 75.3 (103.8 + 3 28.8) = 85.9 J / mole
H358 H298
= Cp
T2 T1
H358 = 28.136 kJ / mole
45.
46.
The decreasing order of electron withdrawing group is

NO2 > Cl > OMe
So have NO2 is most strong electron withdrawing group.
BH3
CH3 COOH
CH3 CH = CH2
( CH3 CH2 CH2 )3 B
CH3 CH2 CH3
CH3
51.
H3C
O3 / H2 O / Zn
CH3
H3C CHO
C O
Ozonolysis
Ethanol
2 methyl but 2 ene
H3C
3-propanone
(A)
1% cold alk. KMnO 4
(hydroxylation )
H3C
CH
Br2 / CCl4
H 3C
CH3
Br
Br
H 3C
CH3
CH3
CH3
OH OH
52.
G = 2.303 RT log Keq

= 2.303 (8.314) 298 log 1014
= 79881.87 J
= 79.9 KJ 80 KJ
54.
From the given BE values

1
H0f (N2 O ) = BeNN + (BE )O =O (BE )N=N + (BE )N= O

2
498
= 946 +
418 + 607 = 1195 1025
2
= 170 KJ
Resonance energy = observed Hf calculated Hf = 82 170 = 88 KJ mol1
55.
PbO2 selectively oxides alkyl benzene to benzoic acid even in the presence of an electron
releasing group. If the same conversion is carried out by using KMnO4/OH, the benzene ring will
undergo cleavage.
56.
Lower the reduction potential, stronger is the reducing agent.
57.
O
C
H
BH3 , THF
O
C
H
C
OH
BH3 , THF
O
H
O
CH
60.
Cu2Cl2
H2 C
CH
HC
CH
NH4 Cl
CH2
CH2
HCl
H2C
160
CH
Polymerisation
H2 C
CH
C
Cl
Cl
Neoprene
PART B
Problem 1:
1.1
(a) NaOH + HCl NaCl + H2O

m (solution NaOH) w (NaOH) 50 g 0.04
=
= 0.05 mol
N(NaOH) =
M(NaOH)
40 g mol1
n (HCl) =
50 g 0.01825
= 0.025 mol
36.5g mol1
unreacted: n(NaOH) = 0.025 mol
(b) When 1 mol of water is formed, neutralization heat is:

mct
10g 4.19Jg1K 1 3.4K
Hneutr =
=
= 57000 J mol1
n (H2O)
0.025 mol
(c) NaOH + H2SO4 NaHSO4 + H2O
The temperature of the resulting solution is calculated according to the equation:
m1c1t1 + m2c2t2 = mct
c1 = c 2 = c
m1t1 + m2t2 = mt
m t + m2 t 2 (100 23.4) + (70 20.0)
=
= 220 C
t= 11
m
170
(d) The temperature increase due to the reaction of NaOH with H2SO4 is as follows:
n (H2O) Hneutr
0.025 mol 57000 jmol1
=
= 2K
t =
mc
170 g 4.19Jg1K 1
1.2
The final temperature of the solution: t = 22 + 2 = 24 C

When the solution has evaporated the following reaction is assumed to take place:
NaCl + NaHSO4 Na2SO4 + HCl
Na2SO4 is the dry residue.
m(Na2SO4) = n M = 0.025 mol 142 g mol-1 = 3.55 g
1.3
(i) 2CO + O2 2CO2
2H2 + O2 2H2O
CH4 + 2O2 CO2 + 2H2O
C2H4 + 3O2 2CO2 + 2H2O
O2
_______
14
1.5
1.2
0.6
_________
17.3 parts 5 = 86.5 parts of the air
1.4
200 m3 of the gas ........2 86.5 = 173.0 m3 of the air

+ 20%
34.6 m3
________________
207.6 m3 of the air
(ii) 207.6 : 5 = 41.52 parts of O2 : 2 = 20.76 parts of O2 for 100 m3 of the gas
20.76 4 = 83.04 parts of N2 for 100 m3 of the gas
H2O
N2
O2
Balance:
CO2
(Volume parts)
12.00
3.00
56.20
20.76
28.00
1.20
83.04
17.30
0.60
0.40
0.40
___________________________________________
41.00
4.60
139.24 3.46
Total: 41.00 + 4.60 + 139.24 + 3.46 = 188.30 of volume parts of the gaseous components.
4.60
% H2 O =
100 = 2.44
188.30
139.24
% N2 =
100 = 73.95
188.30
3.46
%O2 =
100 = 1.84
188.30
(a) Reaction with hydrochloric acid:
1.52 g 0.56 g = 0.96 g of a metal reacted and 0.896 dm3 of hydrogen (0.04 mol)
were
formed.
0.96
Combining mass of the metal: 11.2
= 12g
0.896
Possible solutions
Relative atomic mass of
Oxidation number
Element
Satisfying
the metal
12
I
C
No
24
II
Mg
Yes
36
III
Cl
No
MgCl2 + H2
Reaction: Mg + 2HCl
(b) Reaction with sodium hydroxide:
1.52 g 0.96 g = 0.56 g of an element reacted, 0.896 dm3 (0.04 mol) of hydrogen
were
formed.
0.56
Combining mass of the metal: 11.2
= 7g
0.896
Possible solutions
Relative atomic mass of
Oxidation number
Element
Satisfying
the element
7
I
Li
No
14
II
N
No
21
III
Ne
No
28
IV
Si
Yess
Reaction: Si + 2 NaOH + H2O Na2SiO3 + 2 H2
(c) Combining of both elements:
0.96 g Mg + 0.56 g Si = 1.52 g of silicide MgxSiy
0.96g
0.56g
w (Mg) =
= 0.63
w ( Si) =
= 0.37
1.52g
1.52g
0.63 0.37
x:y =
:
= 2 :1
24
28
(d) Reaction of the silicide with acid:

Mg2Si + 4Cl
2MgCl2 + SiH4
n (Mg2Si ) =
n ( SiH4 ) =
1.52g
= 0.02 mol
76gmol1
0.448 dm3
= 0.02mol
22.4 dm3 mol1
(e) Reaction of silane with oxygen

SiH4 + 2O2
SiO2 + 2H2O
V = 1dm3
On the assumption that T = const: p2 =

n1 ( O2 ) =
n2
p1
n1
1dm3
= 0.0446mol
22.4 dm3 mol1
Consumption of oxygen in the reaction:
n ( O2 ) = 0.04 mol
The remainder of oxygen in the closed vessel:

n2 ( O2 ) = 0.0446 mol 0.04 mol = 0.0046 mol
p2 =
1.5
0.0046 mol
p1 = 0.1p1
0.0446 mol
(i) (a) Reduction by hydrogen:
FeO + H2 Fe + H2O
n(Fe) = n(FeO); n(H2O) = n(FeO)
Fe2O3 + 3H2 2Fe + 3H2O
n(Fe) = 2n(Fe2O3); n(H2O) = 3n(Fe2O3)
The mass of iron after reduction: 3.92 g
The total amount of substance of iron after reduction:
n (Fe ) + n (FeO ) + 2n (Fe2O3 ) =
3.92g
= 0.07 mol
56 gmol1
(b) Reaction with copper(II) sulphate:
Fe + CuSO4
Cu + FeSO4
Increase of the mass: 4.96 g 4.72 g = 0.24 g
After reaction of 1 mol Fe, an increase of the molar mass would be
M ( Cu ) M (Fe ) = 64 g mol1 56g mol1 = 8g mol1

Amount of substance of iron in the mixture:
n (Fe ) =
0.24g
= 0.03 mol
8 g mol1
(c) Formation of water after reduction:

0.90 g H2O, i.e. 0.05 mol
0.05 mol = n(Fe) + 3 n(Fe2O3)
By solving equations (1), (2), and (3):
n(FeO) = 0.02 mol
n(Fe2O3) = 0.01 mol
(d) Consumption of acid:

Fe + 2HCl FeCl2 + H2
FeO + 2HCl FeCl2 + H2O
Fe2O3 + 6HCl 2FeCl2 + 3H2O
n(HCl) = 2n(Fe) + 2n(FeO) + 6n(Fe2O3)
= 0.06 mol + 0.04 mol + 0.06 mol = 0.16 mol
A part of iron reacts according to the equation:
Fe + 2FeCl3 3FeCl2
n(Fe) = 0.5 n(FeCl3) = n(Fe2O3)
n(Fe) = 0.01 mol
It means that the consumption of acid decreases by 0.02 mol.
The total consumption of acid: n(HCl) = 0.14 mol
n M 0.14 mol 36.5 g mol1
=
= 68 cm3
V ( 7.3%HCl ) =
w
0.073 1.03 g cm3
(ii) Volume of hydrogen:
Fe + 2HCl FeCl2 + H2
Iron in the mixture: 0.03 mol
Iron reacted with FeCl3: 0.01 mol
Iron reacted with acid: 0.02 mol
Hence, 0.02 mol of hydrogen, i.e. 0.448 dm3 of hydrogen are formed.
Problem 2:
2.1
S + O2
SO2
2.2
2 SO2 + O2
2SO3
2.3
SO3 + H2O
H2SO4
2.4
K2SO4 + 2 H2O
2 KOH + H2SO4
2.5
2SO24 2e
S2O82
2.6
SO2 + 2 KOH
K2SO3 + H2O
2.7
K2S2O3
K2SO3 + S
2.8
K2S2O3 + H2SO4
K2SO4 + S + SO2 + H2O
2.9
H2 + S
H2S
2.10
K2S + 2 H2O
H2S + 2 KOH
2.11
K2S + x S
K2S(x+1)
2.12
K2S(x+1) + H2SO4
K2SO4 + xS + H2S
A: S
E: K2SO4
I: H2S
Problem 3:
3.1
(i)
B: SO2
F: K2S2O8
J: K2S
C: SO3
G: K2SO3
K: K2Sx
D: H2SO4
H: K2S2O3
L: K2S4O6
(unsaturated ketone)
(ii)
CH2
CH3
OH Br
Br
3.2 (i)
O
CH
CH3
CH
CH3
Ph
(ii)
H
OH
Br
CH3
3.3 (i)
O
C
H group
O
(ii)
H2C
3.4 (i)
CH2
ONa
CH2 CH3
A
B
(Willianson's synthesis)
(ii)
(iii)
(iv)
C
Base right
D
Br
D
Br

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PATHFINDER-2013

Maximum Marks: 230.

B. Filling the top-half of the ORS:

C. Question paper format and Marking scheme:

Name of the Candidate : ___________________________________________________________

When NH4Cl is dissolved in H2O, the temperature of H2O decreases it means:

Match the following:

Identify the incorrect statement of the following:

(B) LiH + AlH3 LiAlH4

Identify the correct statement among the following:

Which of the following carbananion is most stable?

The temperature at which the reaction, Ag2 O ( s ) 2Ag ( s ) +

given H = 30.5 kJmol1 and S = 0.066 kJK 1mol1

Which of the following exist as dimer?

1 M solution of CH3COOH should be diluted to ...................... times so that pH is doubled.

Which of the following can be separated by H2S in dil HCl?

Important ore of lead is:

For the reaction

Borane have general formula

NaOCl on heating with NH3 at high temperature gives:

Which of the following statements is correct?

The coefficient of S in the balanced reaction is

Which of the following statement is not correct?

Which of the following statement is/are not true for bond ?

In which reaction, product formation occurs by Saytzeff rule?

Select the correct alternative from the codes given below:

Following reaction occurs at 25oC,

Find H at 358 K for the reaction,

Give the correct increasing order of acid strength.

(A) III > IV > I > II

(B) IV > III > I > II

In the following reaction

For the following compounds

the correct order of basic strength

(B) IV < I < III < II

and formed through carbocation formation

and formed through carbocation formation

and formed through carbon free radical

and formed through carbon free radical

In Castners process some sodium is lost because

For the equilibrium at 298 K

Calculate resonance energy of N2O from the following data:

Consider the following single step conversion:

The reagent (X) in the above reaction is

In the following there are three carbon-oxygen bonds denoted by x, y and z:

Their lengths are in order

(B) x < y < z

The correct IUPAC name of the above compound:

Amount of 50 g of a 4 % sodium hydroxide solution and 50 g of a 1.825 % solution of hydrochloric acid

Calculate the final temperature of the resulting solution.

[1/2+1/2 +1/2+1 marks]

(ii) Determine the composition of combustion products if the gas is burned in a

(ii) What volume of a gas at STP is released?

(a) Substance A is a solid and is insoluble in water.

Structure Elucidation of Organic Compound

(ii) The structure of A.

(i) Draw the structures of C and D.

(ii) Draw the Fischer projection formulae of the isomers of D.

(ii) The structure of B.

Organic Reactions, Mechanisms and Stereochemistry

(ii) Bromocyclopentane, on heating with sodium ethoxide, gives C. Identify C.

(iii) In the above reaction (ii), ethoxide functions as:

When C is reacted with DBr (in dark), a mixture of products is obtained.

Some Characteristic Proton Chemical Shifts