JEE (MAIN + ADVANCED) Examination (2018) (Page # 19)

TM JEE ADVANCED 2018 [PAPER - 1]

[CHEMISTRY]
Section - 1 : (Maximum Marks : 24)
 This section contains SIX (06) questions.
 Each questions has FOUR options for correct answer(s). ONE OR MORE THAN ONE of these
four option(s) is (are) correct option (s).
 For each question, choose the correct option(s) to answer the questions
 Answer to each question will be evaluated according to the following marking chosen.
Full Marks : +4 If only (all) the correct option(s) is (are) chosen.
Partial Marks :+3 If all the four options are correct but ONLY three options are chosen.
Partial Marks : +2 If three or more options are correct but ONLY two options are
chosen, both of which are correct options.
Partial Marks : +1 If two or more options are correct but ONLY one option is chosen
and it is a correct option.
Zero Marks : 0 If none of the options is chosen (i.e., the question is unanswered)
Negative Marks : –2 In all other cases.
- For Example : If first, third and fourth are the ONLY three correct options for a question with
second option being an incorrect option : Selecting only two of the three correct options (e.g., the
first and fourth options), without selecting any incorrect option (second option in this case) will
result in +2 marks. Selecting only one of the three correct options (either first or thrid or fourth
option), without selecting any incorrect option (second option in this case), will result in +1 marks.
Selecting any incorrect option(s) (second option in this case), with or without selection of any
correct option(s), will result in –2 marks.

1. The compound(s) which generate(s) N2 gas upon thermal decomposition below 300°C is (are)
(A) NH4NO3 (B) (NH4)2Cr2O7 (C) Ba(N3)2 (D) Mg3N2
; kS
fxd t ks300°C dsuhpsr ki h; vi ?kVu i j N2 xS
l mRiUu dj r k gS
&
(A) NH4NO3 (B) (NH4)2Cr2O7 (C) Ba(N3)2 (D) Mg3N2
Sol. B, C
NH4NO3 
T 300 C
 N2O + H2O [NH4NO3 
T 300 C
 N2 + O2 + H2O]
explosive
(NH4)2Cr2O7 

 N2 + Cr2O3 + H2O
volcanic reaction

Ba(N3)2 

 Ba + N2 (Method for getting purest form of Nitrogen)
Mg3N2  Ionic conp. (Does not decompose)

2. The correct statement(s) regarding the binary transition metal carbonyl compounds is (are)
(Atomic numbers : Fe = 26, Ni = 28)
(A) Total number of valence shell electrons at metal centre in Fe(CO5 or Ni(CO)4 is 16
(B) These are predominantly low spin in nature
(C) Metal - carbon bond strengthens when the oxidation state of the metal is lowered
(D) The carbonyl C–O bond weakens when the oxidation state of the metal is increased
f} ?kVdh; l a Øe.k /kkr qdkcksZfuy ; kS fxd dsl a nHkZesal ghdFku gS %
(i j ek.kqØeka d : Fe = 26, Ni = 28)
(A) Fe(CO5 ; kNi(CO)4 es a/kkr qdsUnzi j l a ; kst hdks'k by sDVªkW
uksadhdq
y la [ ; k 16 gS
(B) ; seq [ ; r %fuEu pØ.k i zd f̀r dsgksrsgS
(C) /kkr q&dkcZ u ca/k i zcy gksrk gS ] t c /kkr qdhvkW Dl hdj .k voLFkk de gksrhgS
(D) dkcks Z
fuy C–O ca /k nq
cZ
y gksrk gS ] t c /kkr qdhvkW Dl hdj .k voLFkk vf/kd gksrhgS
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Sol B, C
Fe(CO)5 & Ni(CO)4 metal carbonyl has 18e in valence shell
Valence shell electron in metal carbonyl = no. of (n–1) d- electron in metal
+ no. of electron acquired by metal through ligands
[Fe(Co)5] O oxidation no Fe [Ar]3d64s2
valence shell electron = 6 + 2 + 5 x 2 = 18e
[Ni(Co)4] valence shell electron = 10 + 4 x 2 = 18e
zero oxidation no.
Ni [Ar]3d84s2
these are low spin complexes as CO is strong field ligand both complex are dimagnetic with sp3
hybridisation.
CO involves synergic bonding with transition metal

3. Based on the compounds of group 15 elements , the correct statement(s) is (are)

(A) Bi2O5 is more basic than N2O5
(B) NF3 is more covalent than BiF3
(C) PH3 boils at lower temperature than NH3
(D) The N–N single bond is stronger than the P–P single bond
oxZ15 dsr Roksadsvk/kkj i j l gh dFku gS %
(A) Bi2O5, N2O5 l svf/kd {kkj h; gS
(B) NF3, BiF3 l svf/kd l gl a; kst hgS
(C) PH3, NH3 dh vi s {kk de r ki i j mcy r k gS
(D) N–N , dy ca /k] P–P , dy ca /k l si zcy gksrk gS
Sol. A,B,C
Bi2O5 & N2O5 Bi2O5 is Metallicoxide (Basicoxide) as Bi has high metallic character
same for NF3 & BiF3
Boiling point NH3 is more than PH3 due to H-Bonding N–N Bond is weaker than P–P bond due to
repulsion of non bonding electron present in Nitrogen of relatively small size.

4. In the following reaction sequence, the correct structure(s) of X is (are)

Me N3
(1) PBr3, Et2O
X
(2) NaI, Me2CO
(3) NaN3, HCONMe2
enantiomerically pure

Me OH Me OH
(A) (B) (C) (D)
Me OH Me OH

fuEu vfHkfØ; k vuq

Øe esa
] X dhl ghl a
j puk gS
%
Me N3
(1) PBr3, Et2O
X
(2) NaI, Me 2CO
(3) NaN3, HCONMe 2
i zfr fcEc l eko; fod : i l s' kq
}

Me OH Me OH
(A) (B) (C) (D)
Me OH Me OH

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 JEE (MAIN + ADVANCED) Examination (2018) (Page # 21)

Sol. B

Me N3
(1) PBr3Et2O
X
(2) NaI, Me2C = O
(3) NaN3, HCONMe2

Me OH
all the three reaction are SN2 so X is

5. The reaction(s) leading to the formation of 1,3,5-trimethylbenzene is (are)

O Conc. H2SO 4 heated iron tube

(A) (B) Me H
873 K

O
1. Br2, NaOH CHO
2. H3O+
Zn/Hg, HCl
(C) (D)
OHC CHO
O O

vfHkfØ; k ft l esa1,3,5-VªkbZ
esfFky csUt hu dk fuekZ
. k gksrk gS
%
O Conc. H2SO 4 heated iron tube
(A) (B) Me H
873 K

O
1. Br2, NaOH CHO
2. H3O+
Zn/Hg, HCl
(C) (D)
OHC CHO
O O

Sol. A, B, D

O
Conc H2SO4
(A) (B) Me H

O COOH

1. Br2, NaOH 3. Soda lime

(C) 2. H3O+
HOOC COOH
O O

CHO

(D) Zn/Hg, HCl

OHC CHO
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6. A reversible cyclic process for an ideal gas is shown below. Here, P, V and T are pressure , volume
and temperature , respectively. The thermodynamic parameters q, w, H and U are heat, work,
enthalpy and internal energy, respectively.
A(P1,V1,T1) C(P2,V 1,T2)

Volume (V)
B(P2,V2,T1)

Temperature (T)
, d vkn' kZxS
l dsfy , mRØe.kh; pØh; i zØe uhpsn' kkZ ; k x; k gS A ; gk¡ P, V r Fkk T Øe' k%nkc] vk; r u r Fkk r ki gS
A
Å"ekxfr dh; eki ka
d q, w, H r FkkU Øe' k%Å"ek] dk; Z
] , UFksYi hr Fkk vka
r fj d Åt kZgSA

A(P1,V1,T1) C(P2,V 1,T2)

vk; r u (V)

B(P2,V2,T1)

r ki (T)

Sol. B, C
‘AB’  isothermal
UAB = 0
WAB = –qAB = –nRT1n (V2/V1)
= nRT1 n (V1/V2)
AC isochoric
WAC= 0
qAC = AC = nCv (T2 – T1)
HAC = UAC + (PV)
= nCV(T2 – T1) + nR (T2 – T1)
= nCp (T2 – T1)
qCA = UCA
= nCV (T1 – T2)
= (–)ve
HCA = nCp(T1 – T2)
= (–)ve
BC Isobaric
WBC = –nR(T2 – T1)
= –P2 (V1 – V2) = P2(V2 – V1)
UBC = m Cv (T2 – T1)
qBC = UBC – WBC
= nCv (T2 – T1) + nR(T2– T1)
= ncp (T2 – T1)
qAB + qBC + qCA + WAB + WBC + WCa = 0 (qAB = WAB, WCA = 0)
UBC + qCA = 0
qAC = UBC
qBC = HAC = nCp (T2 – T1)

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 JEE (MAIN + ADVANCED) Examination (2018) (Page # 23)

7. Among the species given below, the total number of diamagnetic species is____.

H atom, NO2 monomer, O2 (superoxide), dimeric sulphur in vapour phase,

Mn3O4, (NH4)2[FeCl4], (NH4)2[NiCl4], K2MnO4, K2CrO4

uhpsnhxbZLi h'kht ksaesal si zfr pq
Ecdh; Li h'kht ksadhdq
y la
[ ; k gS
%
H i j ek.kqNO2 , dy d O2 (l q
i j vkW
Dl kbM), ok"i voLFkk esaf} y dh; l YQj
Mn3O4, (NH4)2[FeCl4], (NH4)2[NiCl4], K2MnO4, K2CrO4
Sol. 1

H– atom = 1 Paramagnetic
1s1

N
NO2 = odd electron species Paramagnetic
O O

O2 (superoxide) = One unpaired electrons in * M.O.. Paramagnetic

S2 (in vapour phase) = same as O2, two unpaired e– s are present in * M.O. Paramagnetic
2 4
Mn3O4 = 2 MnO . MnO2 Paramagnetic
(NH4)2[FeCl4] = Fe +2
= 3d 4s
6 0

Paramagnetic

Cl Cl Cl Cl

sp3 – hybridisation
(NH4)2 [NiCl4] = Ni = 3d8 4s2
Ni = 3d8 4s2

Paramagnetic

Cl Cl Cl Cl

sp3 – hybridisation

Mn
K2MnO4 = 2K+ , Mn+6 = [Ar]3d1 Paramagnetic
O O O

Cr
K2CrO4 = 2K+ , Cr+6 = [Ar]3d0 `Diamagnetic
O O O

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8. The ammonia prepared by treating ammonium sulphate with calcium hydroxide is completely
usedby NiCl2.6H2O to form a stable coordination compound. Assume that both the reactions are
100% complete. If 1584 g of ammonium sulphate and 952g of NiCl2.6H2 O are used in the
preparation, the combined weight (in grams) of gypsum and the nickel-ammonia coordination
compound thus produced is___.
(Atomic weights in g mol–1: H = 1, N = 14, O = 16, S = 32, Cl = 35.5, Ca = 40, Ni = 59)
dsfY' k; e gkbMªksDl kbMdsl kFkveksfu; e l YQsV dhfØ; k} kj kfufeZ
r veksfu; k] NiCl2.6H2O dsl kFki w
. kZ: i l si z;q
Dr gksd j
, d LFkk; h mi l gl a
; kst d ; kS
fxd cukr h gS
A ekuk nksuksavfHkfØ; k, a100% i w . kZgksrh gS
A ; fn foj pu esa1584 g veksfu; e
l YQsV r Fkk952g, NiCl2.6H2O i z;q Dr gksrsgS
] r ksfufeZ
r gq, ft Il e r Fkkfudy veksfu; kmi l gl a ; kst d ; kS
fxd dk; q
fXer
Hkkj ¼xzke esa
½
(i j ek.kqH
kkj ] g mol–1 esa: H = 1, N = 14, O = 16, S = 32, Cl = 35.5, Ca = 40, Ni = 59)
Sol. 2992
69+36
(NH4)2SO4 + Ca(OH)2 2NH3 + [CaSO4 + H2O]

1584gm
= 12mol 24mol CaSO4.2H2O
132amu
12mol
6NH3 + NiCl2.6H2O  [Ni(NH3)6]Cl2 + 6H2O
24mol 4 mol 232

232 × 4 + 12 × [40+96+36] = 920 + 8 + 132 + 80 + 172 × 12

= 928 + 2064 = 2992

9. Consider an ionic solid MX with NaCl structur. Construct a new structure (Z) whose unit cell is
constructed from the unit cell of MX following the sequential instruction given below. Neglect fthe
charge balance.
(i) Remove all the anions (X) except the central one
(ii) Replace all the face centered cations (M) by anions (X)
(iii) Remove all the corner cations (M)
(iv) Replace the central anion (X) with cation (M)
number of anions 
The value of number of cations in Z is ____________ .
 
ekuk, d MX vk; fud Bksl NaCl i zd kj dhl a j pukj [ kr kgS
A, d u; hl aj puk(Z) cukb, t ksuhpsfn, x, vuq
ns'kdki ky u
dj r sgq , MX dhbdkbZdksf"Bdk l sfufeZ r gksrhgS
A vkos'k l arq
y u dksux.; ekur sgS A
(i) , d ds Unzh; vk; u dsvy kok l Hkh_ .kk; uksa(X) dkseq Dr dj r sgS
(ii) _ .kk; uks a(X) } kj k Qy d dsfUnzr /kuk; uksa(M) dksfoLFkkfi r dj r sgS
(iii) l H khdksusds/kuk; uksa(M) dkseq Dr dj r sgS
(iv) /kuk; u (M) dsl kFk ds Unzh; _ .kk; u (X) dkseq Dr dj r sgS
 _ .kk; uksadhl a[; k
Z es a /kuk; uksadh l a
 [ ; k  dk eku g% S
Sol. 3

(i) (ii) (iii) (iv)

1 1 1 1 1 M0 M1×1
M 6× +8× M 6× +8× M8 ×
2 8 2 8 8
1
X 12× +1×1 X X 1 X 1×1+6× 1 X 1
4 1×1 1×1+6× 6×
2 2 2

No. of anions = 3
No. of cations = 1
Ans. 3/1
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 JEE (MAIN + ADVANCED) Examination (2018) (Page # 25)

10. For the electrochemical cell,

Mg(s)Mg2+(aq, 1M) Cu2+ (aq, 1M) Cu(s)

the standard emf of the cell is 2.70 V at 300 K. When the concentration of Mg2+ is changed to x
M, the cell potential changes to 2.67 V at 300 K. The value of x is____.

F
(given,  11500KV–1 , where F is the Faraday constant and R is the gas constant, In(10) = 2.30)
R
, d fo| q
r j kl k; fud l sy
Mg(s)Mg2+(aq, 1M) Cu2+ (aq, 1M) Cu(s)

dsfy , 300K i j l sy dk ekud emf, 2.70V gS A t c Mg2+ dhl kUnzrk x M esai fj ofr Z
r gksrhgS
] r ks300K i j l sy foHko
2.67 V esai fj ofr Z
r gkst kr k gS
A x dk eku gS
%
F
(fn; k gS
,  11500KV–1 , t gk¡F QsjkMsfu; r ka
d r FkkR xS
l fu; r ka
d gS
, In(10) = 2.30)
R
Sol. 10
Mg(s) + Cu2+(aq)  Mg2+(aq) + Cu(s)
E°Cell = 2.70 ECell = 2.67 Mg2+ = x M
Cu2+ = 1 M

RT RT
ECell = E°Cell – ln x = 2.67 = 2.70 – ln x
nF 2F

R  300 0.03  2 F
–0.03 = – × ln x = lnx = ×
2F 300 R

0.03  2  11500
= = lnx = 2.30 = ln(10) = x = 10
300  1

11. A closed tank has two compartments A and B, both filled with oxygen (assumed to be ideal gas).
The partition separating the two compartments is fixed and is a perfect heat insulator (Figure 1).
If the old partition is replaced by a new partition which can slide and conduct heat but does NOT
allow the gas to leak across (Figure 2), the volume (im m3) of the compartment A after the
system attains equilibrium is_____.
, d ca n Vsa
d nksHkkx A r FkkB esafoHkkft r gSr Fkk nksuksavkW Dl ht u (vkn' kZxSl dsvuq fn' k) l sHkj sgq
, gS
A nksuksaHkkxksadks
foHkkft r dj usoky k foHkkt d fLFkj gSr Fkk i zcy Å"ekj ks/khgS(fp=k1)A; fn i qj kusfoHkkt d dksu; sfoHkkt d l sfoLFkkfi r dj
fn; k t k, t ksfQl y l dr k gSr Fkk Å"ek dk pky u dj r k gS ] fdUr qxS
l dksfj l usughansrk gS(fp=k2)Ar ksfudk; dsl kE;
i zkIr dj usdsi ' pkr ~Hkkx A dk vk; r u (m3 esa ) Kkr dj ks %

1m3,5bar 3m3, 1 bar, 300 K

400 K B
A

Figure 1

A B

Figure 2

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Sol. 2.22
P & T both will be same in both container there fore
V
= const
n
V1 V2
n1 = n2
v 4  v
51 = 1 3
R  400 R  300
4v 12  3V
=
5 3
1 2V + 15V = 60
27V = 60
20
= v 2.22
9

12. Liquid A and B form ideal solution over the entire range of composition. At temperature T, equimolar
binary solution of liquids A and B has vapour pressure 45 T orr. At the same temperature, a new
solution of A and B having mole fraction xA and xB, respectively, has vapour pressure of 22.5 Torr.
The value of xA/xB in the new solution is _______.
(given that the vapour pressure of pure liquid A is 20 Torr at temperature T)
nzo A r FkkB l a?kBUk dhi w. kZi j kl i j vkn' kZfoy ; u cukr sgSA r ki T i j nzoksaA r FkkB dk f} ?kVdh; foy ; u ok"i nkc 45
Torr j [ kr k gS
A ml hr ki i j A r FkkB dk u; k foy ; u Øe' k%xA r FkkxB eksy i zHkkt j [ kr k gS ] ft l dk ok"i nkc 22.5 Torr
gS
A u; sfoy ; u esaxA/xB dk eku gksxk%
(fn; k gSfd r ki T i j ' kq
} nzo A dk ok"i nkc 20 Torr gS )
Sol. 19
P°A + P°B = 90
xAP°A + (1 – xA) P°B = 22.5
P°A = 20
 P°B = 70
45
20xA + (1 – xA)70 =
2
45
70 – 50xA =
2
95
xA =
100
xA 0.95
xB = 0.05 = 19
13. The solubility of a salt of weak acid(AB) at pH 3 is Y × 10–3 mol L–1. The value of Y is___.
(Given that the value of solubility product of AB (Ksp) = 2 × 10–10 and the value of ionization
constant of HB(Ka) = 1 × 10–8)
pH = 3 i j nq cZ
y vEy (AB) dsy o.k dh?kq y u' khy r k Y × 10–3 mol L–1 gS
A Y dk eku gksxk%
(fn; k gSfd AB dk foy s
; r k xq
. kuQy (Ksp) = 2 × 10–10 r FkkHB dk vk; uu fLFkj ka
d (Ka) = 1 × 10–8) gS
A
Sol. 0.95
AB  A+ + B–
y× 10 –3
y× 10–3 [B–] [y × 10–3] = 2 × 1010 ....(1)
B –
+ H+
 HB
y×10–3 10–3
[B  ][103  x]
y × 10–3 – x 10–3 – x x, = 10–8 ....(2)
x
(1)  (2)
y  103 2  1010
x
= = 2 × 10–2
10 3
x  108

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 JEE (MAIN + ADVANCED) Examination (2018) (Page # 27)

y2  103 y2 2000
= 2 × 10–2
 =
1  y  1y 100
y2 + 20y – 20 = 0
20  400  80
y=
2
21.90  20 1.90
y= = = 0.95
2 2
14. The plot given below shows P–T curves (where P is the pressure and T is the temperature) for two
solvents X and Y and isomolal solutions of NaCl in these solvents. NaCl completely dissociates in
both the solvents.

1 2 3 4

760
Pressure (mmHg)

1. solvent X
2. solution of NaCl in solvent X
3. solvent Y
4. solution of Nacl in solvent Y
360
362

367
368

Temperature (K)
On addition of equal number of moles a non-volatile solute S in equal amount (in kg) of these
solvents, the elevation of boiling point of solvent X is three times that of solvent Y. Solute S is
known to undergo dimerization in these solvents. If the degree of dimerization is 0.7 in solvent
Y, the degree of dimerization in solvent X is ___.
uhpsfn; k x; k oØ nksfoy k; dksaX and Y r Fkk bu foy k; dksaesaNaCl dsl eeksy y foy ; uksadsfy , P–T oØ (t gk¡P nkc
r Fkk T r ki gS
) n' kkZ
r k gS
ANaCl nksuksafoy k; dksaesai w
. kZfo; ksft r gkst kr k gS
A

1 2 3 4

760

1. foy k; d X
nkc (mmHg)

2. foy k; d X es
aNaCl dk foy ; u
3. foy k; d Y
4. foy k; d Y es
aNacl dk foy ; u
360
362

367
368

r ki (K)
bu foy k; dksadhl eku ek=kk(kg esa ) esa, d vok"i ' khy foy s; S dseksy ksadhl eku l a
[ ; kfey kusi j foy k; d X dsDoFkkukad
esafoy k; d Y dk r hu xq
uk mUu; u gksrk gS A foy s; S bu foy k; dksaesaf} y dhdj .k dsfy , t kuk t kr k gS
A ; fn foy k; d Y esa
f} y dhdj .k dhek=kk0.7 gS A r ksfoy k; d X esaf} y dhdj .k dhek=kk gksxhA
Sol. 0.05
Tb(x) = 360
Tb(x) = 2 = i × kb(x) × m
Tb(y) = 367
Tb(y) = 1 = i × kb(y) × m

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kb  x  2
kb  y  = 1
Tb(x) = 3 T2(y)
ix × kb(x) × m = 3 × iy + kb(y) × m
2 × [1 + (1/2–1)] = 3 × [1 + (1/2 – 1)0.7]
3
[1 –/2] = [1 – 0.35] = 3/2 × 0.65
2
3
/2 = 1 – × 0.65
2
 = 2 [1 – 0.975]
 = 2 × 0.025 = 0.05

Paragraph "X"
Treatment of benzene with CO/HCl in the presence of anhydrous AlCl3/CuCl followed by reaction
with Ac2O/NaOAc gives compound X as the major product. Compound X upon reaction with Br2/
Na2CO3, followed by heating at 473 K with moist KOH furnishes Y as the major product. Reaction
of X with H2/Pd-C, followed by H3PO4 treatment gives Z as the major product. (There are two
questions based on PARAGRAPH "X", the question given below is one of them)
csUt hu dkCO/HCl dsl kFk fut Z
y h; AlCl3/CuCl dhmi fLFkfr esami pkj r FkkfQj Ac2O/NaOAc dsl kFk vfHkfØ; kdj okus
i j eq
[ ; mRikn ds: i esa; kS
fxd X i zkIr gksrkgS
A; kS
fxd X, Br2/Na2CO3 dsl kFkvfHkfØ; kr FkkfQj vknzZKOH dsl kFk473
K i j xeZdj usi j eq
[ ; mRikn ds: i esaY cukr k gS A ; kS
fxd X, H2/Pd-C dsl kFkvfHkfØ; k r Fkk fQj H3PO4 dsl kFk mi pkj
i j eq
[ ; mRikn ds: i esaZ nsrk gSA(vuq PNsn "X" i j vk/kkfj r nksi z'u gS
] muesal s, d i z'u uhpsfn; k x; k gS
)
15. The compound Y is :–
; kS
fxd Y gS
%
OH
COBr Br

(A) (B)

HO O
Br
COBr

(C) (D)
Br
Sol. C
CHO Peek in CH=CH—COOH
condensation
CO + HCl AC2O
AlCl 3/CuCl ACONa
Gatter mann (X)
Koach RXn
Br2/Na2CO3

Br Br
C CH CH—CH
moist KOH
473 K COONa
Elementary Rxn

(1) H2 Pd–C
(X)
(2) H3PO4

(Z)

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 JEE (MAIN + ADVANCED) Examination (2018) (Page # 29)

Paragraph "X"
Treatment of benzene with CO/HCl in the presence of anhydrous AlCl3/CuCl followed by reaction
with Ac2O/NaOAc gives compound X as the major product. Compound X upon reaction with Br2/
Na2CO3, followed by heating at 473 K with moist KOH furnishes Y as the major product. Reaction
of X with H2/Pd-C, followed by H3PO4 treatment gives Z as the major product.
(There are two question based on PARAGARAPH "X", the question given below is one of them)
csUt hu dkCO/HCl dsl kFk fut Z y h; AlCl3/CuCl dhmi fLFkfr esami pkj r FkkfQj Ac2O/NaOAc dsl kFk vfHkfØ; kdj okus
i j eq[ ; mRikn ds: i esa; kS
fxd X i zkIr gksrkgS
A; kS
fxd X, Br2/Na2CO3 dsl kFkvfHkfØ; kr FkkfQj vknzZKOH dsl kFk473
K i j xeZdj usi j eq[ ; mRikn ds: i esaY cukr k gS A ; kS
fxd X, H2/Pd-C dsl kFkvfHkfØ; k r Fkk fQj H3PO4 dsl kFk mi pkj
i j eq[ ; mRikn ds: i esaZ nsrk gSA(vuq PNsn "X" i j vk/kkfj r nksi z'u gS
] muesal s, d i z'u uhpsfn; k x; k gS
)
16. The compound Z is :-
; kS
fxd Z gS
%

(A) (B)

O O
OH

(C) (D)

Sol. A
CHO CH CH—COOH

CO + HCl AC2O
AlCl3/CuCl ACONa

(X)

Br2/Na2CO3

Br Br
CH—CH OH
–CO 2
COONa Ph—CH—CH—Br

OH
Ph—CH CHBr

Ph—C CH
(Y)

Paragraph "A"
An organic acid P (C11H12O2) can easily be oxidized to a dibasic acid which reacts with ethyleneglycol
to produce a polymer dacron. Upon ozonolysis, P gives an aliphatic ketone as one of the products.
P undergoes the following reaction sequences to furnish R via Q. The compound P also undergoes
another set of reactions to produce S.

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(Page # 30) JEE (MAIN + ADVANCED) Examination (2018)

, d dkcZ fud vEy P (C11H12O2) l j y r k l s, d f} {kkj dh; vEy esavkW Dl hdr̀ gksl dr k gSt ks, fFky huXy kbdksy dsl kFk
fØ; k i j , d cgq y d MsØksu cukr k gS
A vkst ksuksi?kVu i j P , d mRikn ds: i esa, sfy QsfVd dhVksu nsrk gS A
P fuEu vfH kfØ; kvuqØe dk vuq l j .kdj r sgq, Q } kj kR cukr k gS
A ; kS
fxd P , d vU; vfHkfØ; k } kj kmRikn S Hkhcukr k gSA

(1) H2/Pd-C
(1) H2/Pd-C (1) HCl
(3) Br2/NaOH (2) SOCl2 (2) Mg/Et2O
S P Q R
(3) MeMgBr, CdCl2 (3) CO2 (dry ice)
+
(5) H2/Pd-C (4) NaBH 4 (4) H3O

(There are two questions based on PARAGRAPH "A", the question given below is one of them)
(vuq
PNsn "A" i j vk/kkfj r nksi z'u gS
] ft uesal s, d uhpsfn; k x; k gS
)
17. The compound R is:-
; kS
fxd R gS
%

HO2C

(A) CO2H (B)

CO2H CO2H

(C) (D)

Ans. A
Paragraph "A"
An organic acid P (C11H12O2) can easily be oxidized to a dibasic acid which reacts with ethyleneglycol
to produce a polymer dacron. Upon ozonolysis, P gives an aliphatic ketone as one of the products.
P undergoes the following reaction sequences to furnish R via Q. The compound P also undergoes
another set of reactions to produce S.
, d dkcZ fud vEy P (C11H12O2) l j y r k l s, d f} {kkj dh; vEy esavkW Dl hdr̀ gksl dr k gSt ks, fFky huXy kbdksy dsl kFk
fØ; k i j , d cgq y d MsØksu cukr k gS
A vkst ksuksi?kVu i j P , d mRikn ds: i esa, sfy QsfVd dhVksu nsrk gS A
P fuEu vfH kfØ; kvuqØe dk vuq l j .kdj r sgq, Q } kj kR cukr k gS
A ; kS
fxd P , d vU; vfHkfØ; k } kj kmRikn S Hkhcukr k gSA

(1) H2/Pd-C
(1) H2/Pd-C (1) HCl
(3) Br2/NaOH (2) SOCl2 (2) Mg/Et2O
S P Q R
(3) MeMgBr, CdCl2 (3) CO2 (dry ice)
+
(5) H2/Pd-C (4) NaBH 4 (4) H3O

(There are two questions based on PARAGRAPH "A", the question given below is one of them)
(vuq
PNsn "A" i j vk/kkfj r nksi z'u gS
] ft uesal s, d uhpsfn; k x; k gS
)

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99, 8003899588
 JEE (MAIN + ADVANCED) Examination (2018) (Page # 31)

18. The compound S is

; kS
fxd S gS
%

NH 2 H
N
(A) (B) (C) (D)

NH 2 HN

Ans. B
COOH
OH
[O] OH
C11H12O2 dacron
(P)
H+

COOH
COOH

H2Pd/C
H2Pd/C

COOH COOH COCl

SOCl2

McMgCl/CdCl2

O
CONH2 C—Me

Br2 NaOH NaBH4

NH2
OH

(Q)
CHCl3/KOH
HCl

NC NH—CH3
H2

Pd/C

(S)

1. CO2 Mg/Et2O
MgCl Cl
2. H3O

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