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Advanced Level Problem Solving-2323

JEE 2023 | Chemistry
Halogen containing organic compounds & organic concept

*Mark questions are more than one options correct type

1. []

2. []

3. If relative reactivity ratio of 3°, 2° and 1° hydogen atoms for free radical []
chlorination is 5 : 4 : 1 then what is the percent yield of the major product (C) in
above sequence of reaction.

4. Alkenes (A) and (B) yield the same alcohol (C) on hydration. On vigorous oxidation
with K M nO 4 , (A) gives a carbonyl compound (D) and an acid (E) each containing four
carbon atoms. On the other hand, (B) gives an acid (F) and a carbonyl compound (G).
In (G) no two identical groups are attached to the same carbon atom. What is
equivalent mass of F? []

Paragraph for Q. No. 5 – 6 []

Hydrocarbon (A), C 6 H 10 ,on treatment with H 2 N i,H 2 Lindlar catalyst and Na/liquid N H 3 forms
three different reduction products (B), (C) and (D) respectively. (A) does not form any salt
with ammoniacal A gN O 3 solution but forms a salt (E) on heating with N aN H 2 in an inert

solvent. Compound (E) reacts with C H 3I to give (F). Compound (D) on oxidative ozonolysis
gives nbutanoic acid along with other products.
5. How many monochloro derivatives are possible for (B)?

6. Equimolar mixture of (C) and (D) on reaction with B r2 in C C l4 form (X) products. What
is value of X?

7. An organic compound (A) of molecular formula C 5 H 8 when treated with sodium in liquid
ammonia followed by reaction with npropyl bromide yields (B) C 8H 14 . (A) gives a

ketone (C), C 5 H 10O when treated with dilute H 2 SO 4 and H gSO 4 . (B) on oxidation with

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alkaline K M nO 4 gives two isomeric acids (D) and (E) C 4 H 8O 2 . IUPAC name of B is p-

methyl hept-q-yne. The value of sum of p and q is: []

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8. An alkane (A), C 5 H 12 ,on chlorination at 300°C gives a mixture of four different

monochloro derivatives (B), (C), (D) and (E). Two of these derivatives give the same
stable alkene (F) on dehydrohlogeantion. On oxidation with hot alkaline K M nO 4
followed by acidification, (F) gives two products (G) and (H). How many of the
following statements are correct for compound A, B, C, D, E, F and G? []
(i) A is isopentane
(ii) B and C are optically active
(iii) D and E are optically inactive
(iv) A, B, C, D and E are positional isomers
(v) F on ozonolysis form acetone and acetaldehyde
(vi) B and E on dehydrohalogenation form less stable non saytzeff product.
Paragraph for Q. No. 9 – 10
[]

An organic compound (A), C 4 H 4 , on hydrogenation gives compound (B) C 4 H 10 and form white
precipitate with ammonical A gN O 3 solution. The product formed if (A) reacts with one
equivalent of HCl at 40C . Undergoes polymerization then polymer B is formed.

9. Find the number of delocalizable pi electrons in an stable isomer of (A) which can
exist in pure form at room temperature and which on reductive ozonolysis gives only
one product.
10. What is the molecular mass of the major product formed on complete ozonolysis of
polymer ‘B’?

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Paragraph for Q. No. 11 – 12

[]
An organic compound (A), C 8 H 6 , on treatment with dilute sulphuric acid containing mercuric
sulphate gives a compound (B), which can also be obtained from a reaction of benzene with an
acid chloride in the presence of anhydrous aluminium chloride. The compound (B) on reaction
with N H 2  N H 2 /base, gives (C). Identify (A), (B) & (C) :

11. Vapours of compound (A) on passing through red hot Fe tube form trimer (B) having
n sp2 hybrid orbitals. What is value of n?
12. According to Huckels rule compound A contain a close loop of delocalizable (4n  2)
electrons. What is value of n?
*13. The product of which of the following reactions is a vicinal dihalide?
[]
(A) Reaction of ethylene glycol with P  B r2
(B) Reaction of HCl with ethyne
(C) Reaction of HBr with ethyne in the presence of peroxide
(D) Reaction of C l2 with propene in presence of light

Paragraph for Q. No. 14 – 15

[]

An unsaturated hydrocarbon (A), C 6 H 10 in liquid ammonia, on treatment with N aN H 2 gives (B).

(B) on treatment with 1-chloropropane gives (C). (C) on partial reduction in presence of
Lindlar reagent gives (D), C 9 H 18 . (D) on ozonolysis gives 2,2dimethylpropanal and
1butanal.
14. How many atoms in (A) are lying along the straight line?

15. How many diols are formed on reaction of (D) with cold alk. K M nO 4 ?

Paragraph for Q. No. 16 – 17

[]

An unknown compound C 6 H 12 (A) decolourises B r2 water and is oxidized by hot acidified

K M nO 4 to a resolvable carboxylic acid C 4 H 9C O O H (B).
16. How many optically active isomers are possible for (A)?
17. How many monobromo allylic bromo derivatives are formed if optically pure form of (A)
is treated with B r2 in presence of light?

18.

How many of the following statement are correct for above reaction scheme?
[]
(a) (A) and (B) are diastereomers
(b) mixture of (A) and (B) can be separated by fractional distillation
(c) Formation of (A) is stereo selective
(d) Formation of (B) is regio selective
(e) Formation of (C) from (A) involve syn addition
(f) Formation of (C) from (B) involve anti-addition
(g) (C) is optically inactive

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Paragraph for Q. No. 19 – 20

[]

19. How many chiral compounds for C 10 H 12 , are possible that do not decolorize Br2 and
that can be oxidized to phthalic acid.

20. Consider (A) chiral with molecular formula C 10 H 12 and oxidized to PhCOOH. How many

sp2 hybridized orbitals are present in (A)

Find the maximum number of atoms that can present in molecular plane in major product
(P)

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*21. The molecules that will have dipole moment are:

[]
(A) 2,2dimethylpropane (B) trans2pentene
(C) Azzulene (D) 2,2,3,3tetramethylbutane
Reasoning Type
(A) Statement1 is True, Statement 2 is True; Statement2 is a correct explanation for
Statement1
(B) Statement  1 is True, Statement 2 is True; Statement  2 is NOT a correct
explanation for Statement1
(C) Statement  1 is True, Statement  2 is False
(D) Statement  1 is False, Statement  2 is True
22. Statement-1: Boiling point of alkanes increases with increase in molecular weight.
[]
Statement-2: Van der Waal’s forces increase with increase in molecular weight.
23. Statement-1: Iodination of alkanes is reversible.
[]
Statement-2: Iodination is carried out in presence of iodic acid.
24. Statement-1: Acetylene does not react with NaOH.
[]
Statement-2: Acetylene has sp hybridization.
25. Statement-1: Concentrated H2SO4 is used to dry ethane and not ethylene.
[]
Statement-2: Concentrated H2SO4 is a dehydrating agent.
26. Statement-1: Freezing point of neopentane is more than n- pentane.
[]
Statement-2: Increase in van der Waal’s forces increases freezing point.
27. Statement-1: Methane cannot be obtained by Wurtz reaction.
[]
Statement-2: Wurtz reaction leads to the formation of symmetrical alkane having an
even number of carbon atoms.
28. Statement-1: Trans-pent-2-ene is polar but trans-but-2-ene is non-polar.
[]
Statement-2: The polarity of cis isomer is more than trans which are either non-polar
or less polar.
29. Statement-1: Iodination of alkane takes place in presence of HgO or HIO3.
[]
Statement-2: Iodination is very slow and reversible process.
30. Which of the following will have largest heat of combustion?
[]

(A) I
(B) II
(C) III
(D) All will have same heat of combustion because DBE = 1 for all.

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31. []

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

32. 1, 2-Dichloroethane  N aSC H 2C H 2SN a  (P) []

Unknown product (P) of the above reaction is :

(A) (B)

(C) C l C H 2  C H  S  C H  C H 2  C l (D)

33. B r  (C H 2 )3  B r  C H 3 N H 2  Product of the reaction is :

[]

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

Acetone
34. 1-Bromo-4-chlorohexane (1 mole) + NaI (1 mole) 
 Product of the reaction is
: []
(A) C l— C H 2 — C H 2 — CH — C H 2 — C H 3 (B) I C H 2  C H 2  C H  C H 2  C H 3
| |
I Cl
(C) H 2C  C H  C H  C H 2  C H 3 (D) I C H 2  C H 2  C H 2  C H  C H 2  C H 3
| |
Cl Cl
35. On chlorination, an equimolar mixture of ethane and neopentane yields neopentyl
chloride and ethyl chloride in the ratio 2.3 : 1. Which of the following is correct
for primary hydrogen atoms of neopentane compare with that of a 1° hydrogen in ethane
? []
(A) In both cases, equally reactive
(B) Primary hydrogen of neopentane are more reactive than primary hydrogen of
ethane
(C) Primary hydrogen of ethane are more reactive than primary hydrogen of
neopentane
(D) Reactivity can’t be compared for chlorination.

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*36. Which of the following is/are correct reaction products?

[]
Br
B r2 /hv
|
(A) C H 3  C H  C H 2  C H 2  C H 3 
CH 3  C C H 2  C H 2  C H 3
| |
CH 3 CH 3

(B)

hv
(C) C H 3  C H 2  C H  C H 2  M e3C O C l 
 (C ) (D )C H 3  C H  C H  C H 2  (C H 3 )3 C O H
|
Cl
CH 3
|
C H 3 C O C l/
|
CH 3
(D) C 6 H 5  C H 2  C H 2  C H 3 
 C 6 H 5  C H  C H 2C H 3  (C H 3 )3 C O H
37. []

What is degree of unsaturation of major product [P] formed in above sequence of

reaction?
38. Correct order of rate of hydrolysis for following compounds is:
[]

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

39. []

The value of X is ________________ .

*40. []

Product possible is/are

(A) (B) (C) (D) SO 2

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Paragraph for Q. No. 41 – 43

[]

O
|| PC l5 x N aN H 2 C H 3I
Reaction-1 : Ph— C — C H 3       Ph— C  C — C H 3

y N aN H
Reaction-2 : 
2
 CH 3— C  C— CH 3

z NaNH Et  I
Reaction-3 : Ph— CH — CH 2  2
   Ph— C C— Et
| |
Cl Cl
x, y, z are moles used.
41. The value of X is ___________ .
42. The value of Y is ___________ .
43. The value of Z is ___________ .
44. 2-Bromo-1, 3-dimethylbenzene is inert to nucleophilic aromatic substitution on
treatment with sodium amide in liquid ammonia. It is recovered unchanged even after
extended contact with the reagent. The lack of reactivity is due to:
[]
(A) Steric crowding at   position (B) Absence of   hydrogen atom
(C) Sodium amide is inert reagent (D) Ammonia of weaker nucleophile
45. How many different alkene can produce only (R)-3-Methyl hexane on catalytic
hydrogenation? []
46. How many stereoisomers are possible for products formed when HCl adds to 2, 4-
Hexadiene? []

47. []

(A) (B)

(C) (D)

*48. Which statement are correct about the reaction given below ?
[]

(A) (i) and (ii) with small amount of (iii) are formed
(B) (iv) and (v) with small amount of (iii) are formed
(C) The two groups undergoing elimination must lie in anti-periplanar arrangement

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(D) Compound (A) has two conformation in which H or D is anti-periplanar to

bromine

Paragraph for Q. No. 49 – 50

[]

49. How many substitution products are formed in above reaction?

50. How many elimination products are formed in above reaction?

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