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Solutions Advanced Level Problem Solving - 2323

JEE 2023 | Chemistry

1.(D)

2.(D)

3.(36.36%)

4.(60) (i) Since alkene (A) on oxidation gives a carbonyl compound (D) and an acid (E) of
four carbon atoms each.

(ii) Hydration of (A) and (B) give the same alcohol.

CH3
H2 O
H3C CH3

(A) CH3
H3C
OH
H3C
H3C CH3 H2 O
(C)
CH3
(B)
(iii) Alkene (A) and (B) give same alcohol on hydration and thus compound (B) can
only be
O

  CH3
 H3C
[O]
H3C CH3 KMnO H3C COOH
4

CH3 Hexan-2-one (G) Acetic acid

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For Q. 5.(5), 6.(3)

The given compound (A) is CH 3–CH2–CH2–CC–CH3 which can be confirmed by the following
reactions.

(ii) (A) is non-terminal alkyne as it does not form salt with ammonical silver
nitrate.
(iii) (A) forms (E) with NaNH2 which reacts with CH3I to give (F).

(iv)

(B) On monochlorination form five monochloro derivative i.e. I-chlorohexane, 2-

chlorohexane (racemic mixture) and 3-chlorobexane (racemic mixture)
(C) On reaction with B r2 / C C l4 form racemic mixture

(D) On reaction with B r2 / C C l4 form meso isomer

7.(5) (i) (A) reacts with sodium in liquid ammonia and thus it is terminal alkyne i.e.
C3H7C  C – H.
Na C H C H C H B r
(ii) 3 2 2
C 3H 7C  C H  C 3H 7C  C  N a 
 C 3H 7C  C  C H 2  C H 2  C H 3
(B )

H gSO
(iii) 4 C H CO  CH
C 3 H 7 C  C H  3 7 3
H 2 SO 4

(iv) [O ]
C 3H 7C  C  C H 2  C H 2  C H 3  C H 3  C H 2  C H 2  C O O H  C 3H 7C O O H
KM nO 4 (D ) (E )

Since (D) and (E) are isomers, thus the structure of (E) is
H3C
COOH
H3C
CH3

H3C H3C
Thus (A) is CH and (B) is
H3C
CH3

O
(c) CH3  CH 2  CH 2  C CH3
IUPAC name of (B) is 2-methylhept-3-yne.

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8.(4) (i), (iv), (v) and (vi) are correct statements.

As alkane (A), C5H12, on chlorination gives four monochloro product and thus (A) is
isopentane.
CH3
(A)
CH3  CH2  CH  CH3

Me Me Me CH2Cl
CH2Cl  CH2  CH CH3  CHCl  CH CH3CH2CCl CH3  CH2  CH
Me Me Me CH3
(B) (C) (D) (E)
(C) & (D) give same stable product on dehydrohalogenation.
Me
alc. KOH
C and D   
 CH3  CH = C
HCl
(F) Me
Stable, saytzeff product

O
KMnO 4
F  
 CH3COOK + CH3  C  CH3

H+ (acidification)

H3C
CH3COOH + C=O
(G) H3C (H)
For q. no. 9.(0) – 10.(120)
Reaction of A with ammonical A gN O 3 indicate presence of terminal alkyne. Hence
structure of A is H C  C  C H  C H 2 .

Reductive ozonolysis of (A) gives C H 2 O and 2-keto-propan-1, 3-diol.

9.(0) Cyclobut-1, 3-diene. Its rectangular form is stable due to non-aromatic nature. Both
pi-bonds are in conjugation but are not delocalizable due to longer C 2  C 3 bond.
10.(120)
The product formed on reaction of A with one equivalent of HCl is chloroprene
(C H 2  C (C l) C H  C H 2 )and polymer is neoprene.

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For Q. 11.(72), 12.(1)

(a) Molecular formula suggests that (A) is
CH

(b) O
CH

2
CH3

Hg / H2SO4 (dil.)


(A) (B)
(c) O

O
CH3
 H3C 
AlCl3
Anhydrous

Cl
(B)
13.(AC)
For Q. 14.(4) 15.(2)
(A): (CH3)3CC  CH (B): (CH3)3CC  CNa+
(C): (CH3)3CC  C  CH2CH2CH3 (D): (CH3)3CCH = CHCH2CH2CH3
Reactions involved are
Only terminal alkyne reacts with NaNH2
N aN H
(CH3)3CC  CH 
2
 (CH3)3CC  CNa+
(A) (B)

(CH3)3CC  CNa+ + ClCH2CH2CH3 

 (CH3)3CC  C  CH2CH2CH3
(B)
(C)
Lindlar
(CH3)3CC  C  CH2CH2CH3 + H2 
 (CH3)3CCH = CHCH2CH2CH3
catalyst
(C)
(D)
CH 2
ozonolysis
|

 C H 3  C  C H O  C H 3 C H 2C H 2C H O
|
CH 3
(D) is cis alkene and it form racemic mixture on syn hydroxylation using cold
alk. K M nO 4

For Q. 16.(2) 17.(4)

C 6 H 12 (A) decolourises B r2 water  A is unsaturated compound.
Molecular formula of
(A) Suggested (A) is alkene with one (C = C) bond.
(B) has five carbon atoms which indicates that terminal carbon is lost during
K M nO 4 oxidation. Hence, (C = C) is at terminal position. C H 2  C H  R (A )
Since (B) is resolvable hence, B and hence, R of (A) has chirality. A can be :

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H H
| |
CH 2  CH  C  CH 3 B can be : H O O C  C  CH 3
| |
C H 2C H 3 C H 2C H 3

H H
| K M nO 4
|
C H 2  C H  C  C H 3  C O 2  H O O C  C  C H 3
|  |
C H 2C H 3 C H 2C H 3
(A ) (B )
18.(6) Except (D) all are correct

For Q. 19.(3) 20.(24)

19.(3) The formula reveals a fifth degree of unsaturation in addition to the four of the
benzene ring. This fifth degree of unsaturation must be a ring, not C = C, because
the Br2 test is negative. Production of phthalic acid means the ring is fused to the
benzene ring. This fused ring has the chiral carbon and must be a monoalkyl
substituted fivemembered or dialkylsubstituted four membered ring. Only in
this way we can account for the additional four carbons of the formula.
H Me H
Me
H Et
H
Me

1Methylindane trans1,2Dimethylbenzcyclobutane 1Ethylbenzcyclobutane

20.(24) The extra unsaturation is in the single side chain: (E) is 3phenyl1butene,
CH3CHPhCH = CH2
Eight sp2 hybridized atoms.

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21.(BC) trans-2-pentene and azzulene (due to dipolar structure) will have dipole

moment,

22.(A) Boiling point  Vander Waal’s Force

23.(B) Iodination of alkane is reversible because HI is reducing agent.
24.(B) H of acetylene does not react with NaOH because H is not very acidic.
25.(B) H 2 SO 4 undergoes electrophilic addition reaction with ethylene.
26.(B) Neopentane form more compact structure than n-pentane therefore neopentane has
higher melting point.
27.(A) Statement-2 is correct explanation of statement-1.
2N a
2R  C H 2  C l
 R  C H 2  C H 2  R  2N aC l, R is alkyl or H.
dry ether

28.(B) Resultant dipole moment of 2 polar bond depends upon angle between them.

u resultant  12  2
2
 212 cos 

29.(B) Iodination is very slow and reversible process because C – I bond is weaker
and HI is reducing agent. Hence is carried out in presence of oxidizing agent.
1
30.(C) Heat of combustion  , Ethyl cyclopropane is less stable due to angle strain
stability
and highest so has heat of combustion.

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31.(C)

32.(A)

33.(B)

34.(D)

rate of S N 2 faster at 1° than 2°.

35.(B)

C hlorination
C H 3 — C H 3 
 CH 3 — CH 2 — Cl
(II)
There are twelve 1°–H in neo-pentane and six 1°–H in ethane. If reactivity of 1°–H in
both would have been same, the ratio of products formed should be 2 : 1.
But the products are getting formed in the ratio of 2.3 : 1, which suggests that 1°–H
of neopentane are more reactive than 1°–H of ethane (based on stability of carbon-
free radical formed).
36.(ABCD)

(A) (B) (C) CH 3— CH — CH = CH 2

|
Cl
(D) C H 3 — C H  C H — C H 2C l (E) C 6 H 5 — C H — C H 2C H 3
|
Cl

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37.(7)

38.(A) In (III) aromatic carbocation is formed in, (II) resonance stabilised carbocation, in
(IV) 3°-carbocation, in (I), bridgehead carbocation therefore unstable.
39.(4) On E 2 elimination, products are :

(1) Chiral with fixed configuration (E and Z)

(2) Chiral with fixed configuration (E and Z)

40.(BCD)
There is inversion of configuration at chiral center during reaction of alcohols with
SO C l2 in presence of pyridine or 3°-amine.

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For Q. 41.(2) 42.(3), 43.(2)

Reaction (1) 2 mole N aN H 2 for E 2 and 1 mole for acid-base reaction.
Reaction (2) 2 mole N aN H 2 for E 2 .
Reaction (3) 2 mole N aN H 2 for E 2 and 1 mole for acid base.

44.(B)

45.(3) (R)-3-Methyl-hex-1-ene
(R)-4-Methyl-hex-2-ene

46.(4)

47.(B) PO C l3 (dehydrating agent), dehydration take place by E 2 reaction.

48.(ACD)
For Q. 49.(2) 50.(2)

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