Chemistry Advanced Level Problem Solving (ALPS-5) - Paper

Vidyamandir Classes: Innovating for Your Success
Advanced Level Problem Solving-2205

JEE 2022 | Chemistry
OCOC-I, Organic Halides & Organic Concepts, p-Block Element-II
*Mark questions are more than one options correct type
*1. Consider the reactions T and U.

CH3 CH3
H D   D H  
T: 
EtO K
EtOH U: 
EtO K
EtOH
H Br H Br
CH3 CH3
(A) T gives cis-2-butene with loss of deuterium
(B) T gives trans-2-butene with loss of deuterium
(C) U gives trans-2-butene without loss of deuterium
(D) T gives cis-2-butene without loss of deuterium
*2. Which of the following chloride(s) is/are partially hydrolysed in water ?

(A) BiCl3 (B) PCl3 (C) AsCl3 (D) SbCl3
3. Consider the reaction.
A; Here A is :
(A) (B)
(C) (D) None of these
VMC | Chemistry 1 ALPS-2205| JEE-2022

*4. Which of the following is/are not mentioning major products in the given reactions?
(A)
EtOH
(B)
Br
Br
Ether
(C) ONa
O
NO2 NO2
CF3 RO CF2
(D)
O2 N NO2
*5. Select CORRECT matching out of given oxides:

(A) N 2 O : Colourless gas, neutral towards litmus
(B) NO: Brown gas, neutral towards litmus
(C) N 2 O 3 : Blue, acidic
(D) NO 2 : Brown, acidic
6. ; Major product obtained in this reaction is :
(A) (B)
(C) (D)
*7. Treatment of A and B with conc. HCl gives the same two isomeric alkyl chlorides; then A and B are
(A) (A) = Me3C–CH=CH2 ; (B) = Me3C–CH(OH)Me
(B) (A) = H3C–CH2–CH=CH2 ; (B) = H3C–CH=CH–CH3
OH
(C)
A B
(D) (A) = Me2CH–CH=CH2 ; (B) = Me3C–CH=CH–CH3
*8.  
Some metal salt M  X  when react with conc. H 2SO 4 produces HX acid as a main product according
to given reaction:
2MX  H 2SO 4  M 2SO 4  2HX
‘X’ can be:
(A) F (B) Cl  (C) Br  (D) NO3

9. Product :
(A) (B)
(C) (D)
10. The hyperconjugative stabilities of tert-butyl cation and 2-butene, respectively, are due to
Paragraph for Questions No. 11 - 13

Action of nitric acid on Metals: Nitric acid reacts with most of the metals (except noble metals like gold and
platinum) and nonmetals. Towards its reaction with metals, HNO3 acts as an acid as well as an oxidizing agent.
Like other acids, HNO3 liberate nascent H from metals which further reduces the nitric acid into number of
products like NO, NO 2 , N 2 O, N 2 , NH 2 OH or NH 3 according to the following reactions:
Metal  HNO3  Nitrate  H , 2HNO3  2H  2NO  2H 2O
2HNO3  6H  2NO  4H 2O , 2HNO3  10H  N 2  6H 2 O
2HNO3  16H  2NH 3  6H 2 O
11. Which reactions is used to prepare laughing gas ?

(A) Reaction of Sn with very dil. HNO3 (B) Reaction of Hg with dil. HNO3
(C) Reaction of Zn with dil. HNO3 (D) Reaction of Al with dil. HNO3
12. Gold and Platinum are not soluble in HNO3 but soluble in 1:3 mixture of HNO3 and HCl due to the
formation of respectively :
(A) Au  NO3 3 ,  Pt  NO3 2  (B) H 2  AuCl6  , H 2  PtCl6 
(C) Au  NO3 4  Cl, Pt  NO3 6  Cl2

    (D) H  AuCl4  Cl, H 2  PtCl6 

13. Consider the following reaction sequence :

Metal  M  
very dil.HNO
3
no reaction
Metal  M  3
 light blue solution (A) + gas (B)
con.HNO
Select CORRECT statement.

(A) Gas (B) is diamagnetic (B) Solution (C) contains only NaNO 2 salt
(C) Dark blue solution is paramagnetic (D) Metal (M) is extracted by thermite process
14. Glycerol 

KHSO4
 A 
LiAlH4
 B.
A and B are :
(A) Acrolein, allyl alcohol (B) Glyceryl sulphate, acrylic acid
(C) Allyl alcohol, acrolein (D) Only acrolein (B is not formed)
*15. Which of the following will not form a Grignard reagent on treatment with Mg in dry ether?
(A) BrCH2CH2Br (B) BrCH2CH2CH2Br
(C) BrCH2CH2CH2CH2Br (D) All the three above can form Grignard reagent
PARAGRAPH FOR QUESTIONS 16 - 18

A tertiary alcohol H upon acid catalysed dehydration gives a product I. Ozonolysis of I leads to compounds J
and K. Compound J upon reaction with KOH gives benzyl alcohol and compound L, whereas K on reaction with
KOH gives only M.
16. Compound H is formed by the reaction of :
(A) + PhMgBr (B)  PhCH 2 MgBr
(C)  PhCH 2 MgBr (D)
17. The structure of compound I is :
(A) (B) (C) (D)

18. The structure of compounds J, K and L respectively, are :

(A) PhCOCH3 , PhCH2COCH3 and PhCH2COO K 
(B) PhCHO, PhCH2CHO and PhCOOK 
(C) PhCOCH3 , PhCH2CHO and CH3COO K
(D) PhCHO,PhCOCH3 and PhCOO K
*19. The reactivity of compound Z with different halogens under appropriate conditions is given below:
The observed pattern of electrophilic substitution can be explained by

(A) the steric effect of the halogen
(B) the steric effect of the tert-butyl group
(C) the electronic effect of the phenolic group
(D) the electronic effect of the tert-butyl group

When triatomic gas X3 reacts with an excess of potassium iodide solution buffered with a borate buffer
(pH  9.2), diatomic product Y2 is liberated which can be titrated against a standard solution of sodium
thiosulphate. This is a quantitative method for the estimation of X3 gas in the mixture of X3 and X 2 of some
atom X.
20. X 2 and Y2 are respectively :

(A) Cl2 , I 2 (B) O 2 , I2 (C) N 2 , I2 (D) O2 , H 2
21. When liberated Y2 reacts with sodium thiosulphate it produces (Z). Identify (Z) :
(A) Na 2SO 4 (B) Na 2SO 4  S (C) Na 2S2 O 3 (D) Na 2S4 O 6
22. Which of the following is/are paramagnetic?

(A) Y2 (B) X3 (C) X2 (D) All of these
23. Select INCORRECT statement :

(A) Y2 produces blue colour with starch
(B) X 2 is thermodynamically more stable as compared to X3
(C) Y2 can produce brown colouration due to the presence of excess KI
(D) X 2 and X3 both are colourless and odourless gases
*24. Among the following, the number of reaction(s) that produce(s) benzaldehyde is :

*25. The sequence of reagents used in that order to distinguish the following compounds taken in three
different test tubes.
(1) CH3–CH=CHCl (2) CH3CH2CH2Cl (3) CH2=CH–CH2Cl
would be :
(A) Br2 in CCl4, alcoholic AgNO3
(B) Cold alkaline KMnO4, ammoniacal AgNO3
(C) Alcoholic AgNO3, Br2 in CCl4
(D) Ammoniacal AgNO3, cold alkaline KMnO4
PARAGRAPH FOR QUESTIONS 26 - 28

Acid catalyzed conversion of 1, 2-diol or vicinal diol, into carbonyl compound known as pinacol-pinacolone
rearrangement.
Generally more electron donating group migrate during mechanism, migration of —H is faster because of its
smaller size.
26. What would be the major product of reaction ?
(A) (B) (C) (D)
27.
In this sequence of reaction final product is :
(A) (B) (C) (D)

28. Which of the following is not correct about this rearrangement ?
(A) Migratory order for substituent in phenyl is
(B) The carbocation is stabilized by 1, 2-shift

(C) Migratory aptitude for substituent is in R —  H—  C6 H5
(D) Product of reaction is carbonyl compound
29. Which of the following reaction will proceed with retention of configuration only at the chiral centre ?
C2H5
H
O–
dil. OH–
(A) CH3 – C – C (B) CH3 – C – Br H2O
O
C2H5
Br
CH3
CH3
H2O
(C) C6H5 – C – Br (D) C – CH2 – S – CH3 H2O
Ag+
C2H5 H
I
30. The major product in the following reaction is :
(A) (B)
(C) (D)

The reactions of Cl 2 gas with cold-dilute and hot-concentrated NaOH in water give sodium salts of two
(different) oxoacids of chlorine, P and Q, respectively. The Cl 2 gas reacts with SO 2 gas, in presence of
charcoal, to give a product R. R reacts with white phosphorus to give a compound S. On hydrolysis, S gives an
oxoacid of phosphorus T.
31. P and Q, respectively, are the sodium salts of :

(A) hypochlorus and chloric acids (B) hypochlorus and chlorus acids
(C) chloric and perchloric acids (D) chloric and hypochlorus acids
32. R, S and T respectively, are :

(A) SO 2 Cl 2 , PCl5 and H 3 PO 4 (B) SO 2 Cl2 , PCl3 and H3 PO3
(C) SOCl2 , PCl3 and H 3PO 2 (D) SOCl2 , PCl5 and H 3PO 4

33. Match the Column-I and Column-II :

Column I Column II
(A) Cl is less reactive than Cl (p) S N1
Cl
Cl
(B) CH3 (q) S N2
is less reactive than
Cl
Cl
(C) is less reactive than
(r) E1
CH3 H3C Cl
H3C
(D) C C C C (s) E2
is less reactive than
H H CH3
Cl
*34. What are the expected products of the following dehydration reaction ?
(A) (B) (C) (D)
35.
Column I Column II
H
CH3 Br CH3
(A) alc. KOH (p)
H H CH3–C=CH–CH3
Et
CH3
H H alc.KOH
(B) (q) E2
Et F
H
CH3
H H pot.t.butoxide
CH3
(C) (r)
Et Br CH2=C–CH2–CH3
H
H
CH3 Et pot.t.butoxide
(D) (s) E1CB
H H
F

36. How many of the following solvents are suitable for SN 2 reactions ?


Upon heating KClO 3 in the presence of catalytic amount of MnO 2 , a gas W is formed Excess amount of W
reacts with white phosphorus to give X. The reaction of X with pure HNO3 gives Y and Z.
37. W and X are respectively :

(A) O3 and P4 O6 (B) O 2 and P4 O10 (C) O3 and P4 O10 (D) O 2 and P4 O 6
38. Y and Z are respectively :

(A) N 2 O 4 and H 3 PO3 (B) N 2 O 4 and HPO3
(C) N 2 O5 and HPO3 (D) N 2 O3 and H 3 PO 4
*39. Methanol and ethanol can be distinguished by :

(A) Heating with I2 / NaOH (B) Treatment with Schiff’s reagent
(C) Treatment with H 2 CrO 4 (D) Treatment with acidic KMnO 4
40. Match the Column-I and Column-II :
Column I Column II

(A) CHCl3 
OH
 (p) ElCB mechanism

(B) CHCl 2  CF3 
C2 H5O
(q) Benzyne mechanism
O
(C) Br2/CCl4 (r) , -elimination
R C OAg
NaOH
(D) Cl (s) Free radical mechanism
high temperature pressure
*41. Pick the correct statement :
(A)
(B)
(C)
(D)

42.
Column I Column II
Cl
NO2
(A) NaOH (p) Nucleophilic substitution
NO2
F
(B) EtO–Na+ (q) Elimination
CH3–CH–CH2CH3 in EtOH
CH3
CH3O–Na
(C) CH3–C–Br in MeOH (r) Carbanion
CH3
CH3 E2 E
(D) NaNH2 (s)  1
CH3CH2–CH–CH2–Br in liq. NH3 SN 2 SN 1
43. Match the matrix.

Column –I Column-II
(A)  NH4 2 CO3s 

 (P) No residue obtain

(B) NH4 NO3s    (Q) Brown gas is produced

(C) NH4 NO2s    (R) Same gas is obtained which is obtained by
reaction of calcium nitride + water
(D) Hg  NO3 2s  
 
(S) N 2 is not produced
*44. Consider the following compound . Select the correct statement(s) :
(A) It is more acidic than methanol (B) It is more acidic than acetic acid
(C) It reacts very fast with Lucas reagent (D) It is diacidic
45.
The total number of possible substitution product will be :

Column-I Column-II
(A) HOCl (P) Monobasic acid
(B) HOClO (Q) Most acidic
(C) HOClO 2 (R) Thermal stability is maximum
(D) HOClO3 (S) Most oxidizing
(T) +ve oxidation state of halogen atom

*47. Which of the following gives ether successfully ?
(A)
(B) C2H5ONa  (CH3 )2 SO4 


(C) CH3ONa  CH3CH 2 OSO 2 


(D) (CH3 )3 CBr  C2 H5ONa 


48. The number of uncharged resonating structures of are ________.


Column –I Column-II
(Heating effect) (Related observation)

(A) KClO3 s  
MnO
(P) Produce metal
2

(B) Ag 2Os    (Q) Produce metal oxide

(C) HgOs    (R) No solid product

(D) PbO2s    (S) Produce O 2
*50. The correct statement(s) about the following reaction sequence is/(are) :
Cumene (C9 H12 )  
 P 
CHCl3 / NaOH
 Q(major) + R(minor), Q 
(i) O2 NaOH
PhCH Br
S
(ii) H3O 2
(A) R is steam volatile

(B) Q gives dark violet colouration with 1% aqueous FeCl3 solution
(C) S gives yellow precipitate with 2, 4-dinitrophenylhydrazine
(D) S gives dark violet colouration with 1% aqueous FeCl3 solution
51. On conversion into Grignard reagent followed by treatment with water, how many alkyl bromide would
yield isopentane ?
Match the column :

The following columns-1, 2, 3 represent the various methods for the preparation of nitrogen oxide and their
properties observed.
Answer the question that follow:
Column -1 : Column method for preparation of oxide of nitrogen.
Column -2 : Oxidation number of nitrogen in oxide of nitrogen (in product).
Column -3 : Physical/chemical properties of nitrogen oxide.
Column-1 Column-2 Column-3
Common method for preparation Oxidation number of nitrogen Physical/Chemical properties
of oxide of nitrogen in product oxide of nitrogen of nitrogen oxide
(P) Pb(NO3 )2(s) 

673K (I) + 2 (i) Colourless
(Q) HNO3  P4O10(s) 

 (II) + 3 (ii) Coloured
(R) Cu  dil HNO3 

 (III) + 4 (iii) Neutral for litmus
 (IV) + 5 (iv) Paramagnetic

(S) NH 4 NO3 
Heat

52. Select correct combination for the oxide of nitrogen which is formed by without change in
oxidation number of nitrogen.
(A) (P), (III), (ii) (B) (Q), (IV), (i) (C) (R), (I), (i), (iv) (D) (S), (III), (i), (iii)
53. Select correct for the oxide of nitrogen form when nitrogen oxide of reaction-I and nitrogen oxide of
reaction-III are allowed to cool at 250 K.
(A) (II)  (ii) (B) (III)  (ii), (iv) (C) (IV)  (i), (iii) (D) (II)  (ii), (iii), (iv)

54. Select correct for the oxide of nitrogen which is produced by Ostwald ammonia method.
(A) (Q), (I), (i) (B) (R), (I), (i), (iii), (iv)
(C) (S), (III), (i), (iii) (D) (P), (III), (ii), (iv)
55. Product of following reaction is :
(A) (B) (C) (D)
56. How many structural methyl ketones of molecular mass 100 are possible?
*57. The product(s) of the following reaction is/are :
(A) P (B) Q (C) R (D) S
58. The total number of contributing structure(s) showing hyperconjugation (involving C-H bonds) for the
following species is/are _______.
*59. In the following reaction, the formed is/are :
(A) (P) (B) (Q) (C) (R) (D) (S)
60. How many of the following compounds reac with CH3MgBr to liberate CH4 gas ?

61. Maximum number of halogen atoms possible in uncharged interhalogen compound.
*62. The following conversion reaction can be carried out by using reaction sequences :
Zn  Hg / HCl H  O, 
   

2 3 Br , hv KCN
(A)
Al O , 
    
O / H O (Oxidation)

NaBH
4 2 3 3 2
(B)
 I  NaOH H
(C) 
 
2

 


(D) KMnO4 / OH / 
63. How many of the following compounds can undergo SN1 reaction at significant rate with H 2O ?
64. Consider the following list of reagents.

Acidified K 2 Cr2 O7 , alkaline KMnO 4 , CuSO 4 , H 2 O 2 , Cl2 , O3 , FeCl3 , HNO3 and Na 2S2 O 3 . The total
number of reagents that can oxidise aqueous iodide to iodine is :
*65. Product
Which of the following are possible products in significant amounts ?
(A) (B) (C) (D)
*66. Which of the following reactions will give ether as main product ?
Me3C — OH  
Na
(A) (B) C H Br
6 5
Me3C — OH   CH3CH2CH2OH  

Na Na
(C) CH CH CH Br
(D) Me C—Br
3 2 2 3

67. 
H

 Possible products 
Br2
 Products
x
CCl4
x
OH
The total number of possible products (x + y) (including stereoisomerisms) is/are ________.
68. H2S does not produce metallic sulphide with :

(A) CdCl2 (B) ZnCl2 (C) COCl2 (D) CuCl2
*69. Glycerol can be converted to acrolein by dehydration in presence of :

(A) Conc. H 2SO 4 (B) KHSO 4 (C) CaCl2 (D) Anhyd. ZnCl2

70. How many of the following reactions can be used to prepare Aryl Halide.
CH3
(A) CH2 COOAg 

Br2 /CCl4
 (B) 
Cl2 /h

(C) 
Br2 /CCl4
 (D)
N2Cl
(E) 
HBF4

 (F)
HCl 1/2O 2
 
71. Amongst H 2 O, H 2S, H 2Se and H 2 Te, the one with highest boiling point is :
(A) H2O because of hydrogen bonding
(B) H2Te because of higher molecular weight
(C) H2S because of hydrogen bonding
(D) H2Se because of lower molecular weight
*72. ; Products can be :
(A) (B) (C) (D)
73. How many of the following subtrates will react faster when compared with 1-bromopropane towards
SN1 reaction in similar conditions ?
(i) CH3  CH  CH  Br (ii) CH 2  CH  CH 2 Br (iii) CH3  Br
(iv) C6 H5CH 2 Br (v) C6 H 5 Br (vi)
(vii) (CH3 )3 CBr (viii) (CH 3 ) 2 CHBr (ix)
Br
74. Which of the following has greatest reducing power ?
(A) HI (B) HBr (C) HCl (D) HF
*75. Among the following gemdiols which are stable with respect to corresponding carbonyls :
(A) (B)
(C) (D)

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Vidyamandir Classes: Innovating for Your Success

Advanced Level Problem Solving-2205

*1. Consider the reactions T and U.

*2. Which of the following chloride(s) is/are partially hydrolysed in water ?

3. Consider the reaction.

(C) (D) None of these

VMC | Chemistry 1 ALPS-2205| JEE-2022

*5. Select CORRECT matching out of given oxides:

6. ; Major product obtained in this reaction is :

VMC | Chemistry 2 ALPS-2205| JEE-2022

Paragraph for Questions No. 11 - 13

11. Which reactions is used to prepare laughing gas ?

(C) Au  NO3 4  Cl, Pt  NO3 6  Cl2

VMC | Chemistry 3 ALPS-2205| JEE-2022

13. Consider the following reaction sequence :

Select CORRECT statement.

14. Glycerol 

PARAGRAPH FOR QUESTIONS 16 - 18

16. Compound H is formed by the reaction of :

(A) + PhMgBr (B)  PhCH 2 MgBr

(C)  PhCH 2 MgBr (D)

17. The structure of compound I is :

(A) (B) (C) (D)

VMC | Chemistry 4 ALPS-2205| JEE-2022

18. The structure of compounds J, K and L respectively, are :

The observed pattern of electrophilic substitution can be explained by

Paragraph for Questions No. 20 - 23

20. X 2 and Y2 are respectively :

22. Which of the following is/are paramagnetic?

23. Select INCORRECT statement :

VMC | Chemistry 5 ALPS-2205| JEE-2022

PARAGRAPH FOR QUESTIONS 26 - 28

26. What would be the major product of reaction ?

(A) (B) (C) (D)

In this sequence of reaction final product is :

(A) (B) (C) (D)

VMC | Chemistry 6 ALPS-2205| JEE-2022

28. Which of the following is not correct about this rearrangement ?

(A) Migratory order for substituent in phenyl is

(B) The carbocation is stabilized by 1, 2-shift

Paragraph for Questions No. 31 - 32

31. P and Q, respectively, are the sodium salts of :

32. R, S and T respectively, are :

VMC | Chemistry 7 ALPS-2205| JEE-2022

33. Match the Column-I and Column-II :

(A) Cl is less reactive than Cl (p) S N1

(A) (B) (C) (D)

VMC | Chemistry 8 ALPS-2205| JEE-2022

VMC | Chemistry 9 ALPS-2205| JEE-2022

Paragraph for Questions No. 37 - 38

37. W and X are respectively :

38. Y and Z are respectively :

*39. Methanol and ethanol can be distinguished by :

*41. Pick the correct statement :

VMC | Chemistry 10 ALPS-2205| JEE-2022

43. Match the matrix.

*44. Consider the following compound . Select the correct statement(s) :

The total number of possible substitution product will be :

46. Match the matrix.

VMC | Chemistry 11 ALPS-2205| JEE-2022

*47. Which of the following gives ether successfully ?

(B) C2H5ONa  (CH3 )2 SO4 

(C) CH3ONa  CH3CH 2 OSO 2 