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Solutions to Advanced Level Problem Solving-2206

JEE 2022 | Chemistry
OCOC-I, Organic Halides & Organic Concepts, p-Block Element-II,
Practical Organic Chemistry & Polymer

1. [A-q] [B-p] [C-s] [D-r]

(A) MPV reduction of  C  O (keto) group will take place
(B) With NaBH 4 , both keto and acid-chloride groups will be reduced
(C) With DIBAL-H acid derivatives is reduced
(D) LiAlH 4 reduces the left —COOH group

2.(3) Attack by  OMe on Cl(3) would form a carbanion, which can be stabilized by –R effect of NO2 group,
this Cl(3) is substituted by  OMe.
3.(B) HCl is most volatile due to weakest inter molecular attractive forces. While HF is least volatile because
of H-bonding.

4.(B) Phenols give violet colour with Fe Cl3 solution while alcohols do not.

5. [A-p, q, t] [B-r, s] [C-v] [D-u]

(A) All (p), (q), (t) gives this alcohol via Grignard synthesis
(B) Only (r) and (s) can give this alcohol via Grignard synthesis
(C) Only (v) can give this alcohol

(D)

6.(9) Aromatic species : 1, 3, 8, 9, 10, 11, 12, 13, 14.

7.(C) I  I bond is the weakest bond.

RCOOH 
 RCONH 2 
H O
  NH3  RCOOH
8.(B) 2
H
n NH3  1  n RCONH2
 Mo(amide)  59g  Mo(acid)  59  15  16  60g i.e. CH3COOH

9. [A-p, q] [B-p, q] [C-q, r] [D-q]

Other mechanisms can be done similar way.

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10.(8) The decreasing order of B.P.’s is: (3) > (8) > (2) > (6) > (7) > (1) > (4) > (5)
The sum of numbers pertaining to compounds with lowest & highest B.P. is 5 + 3 = 8.
11.(C) Xe form compounds with fluorine and oxygen and heavier noble gases can be easily liquefied.
38.7
12.(A) %C  38.7   3.225mol
12
16.17
%H  16.17   16.17 mol
1
45.17
% N  45.17   3.225mol
14
Divide by 3.225
C = 1, H = 5, N = 1
So, empirical formula is CNH5 i.e. CH 3 NH 2 .

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13. [A-q] [B-r] [C-p] [D-s]

14.(B) XeF4 is square planar and sp3d2 hybridized.

15.(D) CAN is a test of  OH group and not  COOH group.

16. [A-q, s] [B-p, r, s] [C-p, s] [D-p, r]

Other mechanisms can be done similar way.

17.(A) Zn  2NaOH 
 Na 2 ZnO2  H2 ; Zn  H2SO4 
 ZnSO4  H2

 y y
18.(D) CX H y   x   O2  xCO2  H 2O
 4 2
20
Moles of organic compound 
12x  y
10y 10
 Moles of H2O    18y  12x  y  17y  12x
12x  y 18
12x
y 7 1
%H  100    100  5.55%
12x  y  1  18
12x 1  
 17 
10
Mass of hydrogen (H 2 ) in the sample   2g
18
( After combustion all the hydrogen in the hydrocarbon will be present in the water formed)
10
2
 % of hydrogen  18  100  5.55%
20
19. [A-q] [B-r] [C-s] [D-p]
CH3CH2CH(OH)CH3 
2 4  CH CH  CHCH (cis  trans)
H SO
(A)  3 3
(Q)

(B)

(C) SN 2 of I  by OH will give overall meso product. (S)

(D)

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20.(D) More reactive halogen can displace less reactive halogen from their salts.

0.35  32
0.35
21.(C) Mass of sulphur   32g  % sulphur  233.43  100  18.5%
233.43 0.2595

22.(4) A =

Number of alcohol = Number of moles of Ac 2 O consumed = 4

23.(B) Cl2  H2O 

 HOCl  HCl

24.(D) Mass of nitrogen  200 103 14g  % of nitrogen 

 200 1 103 14 100  46.67%
6

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25.(2) 2 products are formed during reaction

26.(B) Total electron pairs around central atom are 5 hence its structure is trigonal bipyramidal.

27.(A) Silk is a natural product made from the fibres found in the cocoon of the mulberry silk worm. It is
actually made up of long strands of protein sericin and fibrosin which are polymers of amino acids.

28.(3) Attacking positions are indicated by arrow sign.

29.(D) Na 2S2O3  2HCl 

 2NaCl  SO2  S  H2O ;

Br2  SO2  H2O 

 2HBr  SO3

30.(B) Vulcanised rubber contains linear chains having some branches.

31.(3)

Number of alcohol is number of moles of anhydride consumed  3

32.(D) These are polar covalent compounds like ICl, ClF3 etc.

33.(C) CH3  CH 2  NH 2 has only one functional group, have it can’t undergo self-polymerisation.

m  m
34.(5) Number of hydroxyl group n 
42
Where m   Molcular mass of product
M  Molcular mass of unknown compound
390  180
n 5
42
35.(D) Oxygen cannot form more than three bonds.

36.(B) Polyethyene, PVC and polycryalonitrie (orlon) are addition polymers.

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37.(9)

All the above shown nine resonating structures are different.

38.(D) Sulphur is used for vulcanization of rubber.

39.(C)

(I) gives immediately turbidity by lucas reagent and (II) does not give turbidity appreciably.

40.(4)

2 60
41.(B) 2NaClO3  2NaCl  3O 2 ; w NaClO3   106.5  177.5g
3 24
42.(A) Volume of oxygen produced is equal to area under the curve.

43.(B) BaO 2  2HClO 

 BaCl2  12 O 2  H 2O

44.(C) The compound gives positive test with Na metal, 2, 4-DNP and it gives single product with

O3 .

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45.(3) 2HCHO  3HCOOH  CO 2

46.(B) The compound C30 H 60 O has one degree of unsaturation since it gives negative test with Br2 / H 2 O,
2, 4 - DNP and Na metal it must be an epoxide.

47.(6)

48.(ABCD)
Deacon’s process : 4HCl  O2 
CuCl
723K
2 2Cl2  2H2O
It is also prepared by electrolysis of chloride salt solutions.

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49.(A) Ziegler-Natta polymerization is an example of addition polymerization.

50.(D) All three (A, B & C) correctly represents addition polymerization process.

51.(A) SO 2 can decolourises characteristic colouration of these solution while CO 2 can’t decolourise.

52.(B) Bleaching action of SO 2 is due to its reducing nature. It reduces colouring matter and reduced colouring
matter will restore its colour by oxidation from air.

53.(D) Na 2SO3  S 
 Na 2S2O3

54.(13)

55.(AC)
By the condition of the question I & IV both compounds do not give iodoform test and I and II both give
similar test.

56.(60.56%)
75  85  95 100
Overall % yield   60.56
100 100 100 1

57.(C) A = F; B = I; BA 3  IF3 ; KHA y  KHF2 ; H x A  HF ; H x B  HI

2NaF  H 2SO 4  Na 2SO 4  2HF
2NaI  2H 2SO 4  Na 2SO 4  SO 2  I 2  2H 2O

58.(C) F2 do not disproportionate in water or alkali. F2  H 2O  2HF  O 2

59.(C)

60.(AB)
Methylaniline is the only base in the mixture and benzoic acid is a much stronger acid than phenol.

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61.(174)
Mass of P increases by 42 unit per OH group, molar mass of P is 90 g/mol.

62.(B)

63.(ABC)
Protein, nylon-6, 6 and nylon-6 are polyamide polymers since all of them have amide linkage.

64.(22) Compound ‘Y’ is n-pantane

Compounds ‘Y’ can form total 28 dichloro products and out of these 22 are optically active.
Compound ‘X’  No reaction at room temperature.
Lucas reagent

C5H8O   ppt, X  CH 4 ; X   n-pentane

Ammoniacal Excess of H 2 /Pt
AgNO 3 CH MgBr
3 HI excess

Above information suggest than X has a terminal triple bond and it contain primary —OH group.
Ag(NH )
 H — C  C — CH 2 — CH 2 — CH 2OH 
3 2
 Ag — C  C — CH 2CH 2CH 2OH
X
65.(ABC)
Gallium have very low melting point (303K) it exist in liquid form at or near normal room temperature.
Bromine and mercury are two well-known liquid substances.

66.(CD)
Since here two different substances polymerise, copolymerization is said to have occurred. Also since a
water molecule is lost in the process it is condensation polymerisation.
It involves branching by (C1  C6 ) glycosidic linkage.
67.(8)

68.(ABCD)
Species having unpaired electrons are paramagnetic.
O2 , O2 and S2 are paramagnetic on the basis of molecular orbital theory. In ClO 2 there is unpaired
electron in chlorine atom.

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69.(ACD)
Neoprene is –( CH 2  C  CH  CH 2 –)n
|
Cl
70.(3) Intermediate is 2, 3-dehydroanisole and H-bonded to benzene ring are vinylic H.

*71.(BD)
Inter halogen compounds are all covalent molecules and are diamagnetic in nature. Their physical
properties are intermediate between those of constituents halogens except that their melting point and
boiling point are little higher than excepted. In general, inter halogen compounds are more reactive than
halogens except fluorine.

*72.(AC)
(A) nHOOC  (CH2 )4  COOH  nH2 N  (CH2 )6  NH2 
 Nylon  6,6  H2O
(B) Cellulose triacetate is semi synthetic polymer

(C)

(D) Sucrose is disaccharide

73.(7) b, c, e, h, i, j, k

*74.(ABC)
Comproportionation is reverse of disproportionation

75.(ABCD)

Peptide linkage is an amide linkage capable to form H-bond (hydrophilic in nature) and connects
polypeptide chain in protein through H-bond.

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