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Solutions to Advanced Level Problem Solving-2204

JEE 2022 | Chemistry
OCOC-I, Organic Halides & Organic Concepts, p-Block Element-II,
Biomolecules & Amino Acids

1.(C)

2.(B)  -Haloketones react significantly faster than methyl halides. Methyl halides reacts faster than allyl
halides & tert. halide is the least reactive toward S N2 reaction.

3.(C) IF3 is T-shaped 4.(C)

5.(C)

(Less hindered carbon)

6.(A) The initially formed carbocation is secondary that undergoes hydride transfer to form a tert benzylic
carbocation, that is stabilized by MeO group at para position. This 3º benzylic carbocation is attacked by
H2O to form a 3º alcohol.

7.(D) S1 : (NH4 )2 Cr2O7 
 Cr2O3  N2   4H2O
(orange) (green)

S2 : 4K 2Cr2O7 
 Cr2O3  N2   4H2O
(oarnge) (green)

8.(C) DNA contains adenine (A), guanine (G), cytosine (C), thymine (T) bases. But these is uracil (U) in place
of thymine in case of RNA.
The pair of complimentary bases are, A—T; A—U and G—C

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9.(C)

Both products (A) and (B) can be obtained by NGP (Neighbouring group participation)

10.(D) SN1 reaction would be most preferred with a substrate that gives most stable carbocation (2º allylic).

11.(D) ICl3 exists as I 2 Cl6

CH2OH
H * O H
H
12.(D) * OH H *
HO OH
* *
H OH
The assymmetric C–atom of (D)glucopyranose have been shown by (*).

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13.(A)

14.(B)

15.(A) NO produces brown coloration with aq. FeSO 4


/
16.(A) Glucose + 3C6H5NH–NH2 H  Osazone + C6H5NH2 + NH3 + 2H2O
(A) (B)

17.(A)

18.(C)

19.(B) Order of Acidic strength : H 2 Te  H 2Se  H 2S  H 2 O

20.(BC) CH3–CH–COO Acidic

pH
CH3–CH–COOH
 
NH3 NH3
Basic
pH

CH3–CH–COO
NH2

21.(B)

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22.(C) Compound (B) MF C3H6O on oxidation gives compound of MF C3H6O2.

23.(D) H2S  SO2 /SO32 

 S   H2O
It is con-proportionation reaction

24.(CD)
C6H11O5OH + HOCH3  C6H5O5OCH3 + H2O

Methyl glucoside
&-methyl glucosides are anomers&methoxy group is linked to C-1 atom.

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25.(A)

26.(A) SN 2 reaction would occur preferably at benzylic position with inversion of configuration.

27.(A)

28.(CD)
C6H11O5OH + HOCH3  C6H5O5OCH3 + H2O

Methyl glucoside
&-methyl glucosides are anomers&methoxy group is linked to C-1 atom.

29.(A)

30.(B) Substitution is preferred at low temperature while elimination is favoured at high temperature.

NH4Cl  
NaOH
31.(C) Bond angle 
NH3
(109.5) (107)

PH4 I  
NaOH

PH3
(109.5) (92)

P4 
 PH3 
(60) (92)

Order of change in bond angle  III  II  I

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32.(ACD)

33.(B)

34.(B) In dilute OH  medium, the NGP will occur leading to retention of configuration.

35.(B) Order of oxidizing strength Cl2  conc. H 2SO4  Br 2  I2

36.(AC)
-D-glucose or -D-glucose are anomers.
The constant specific rotation in water with either -D-glucose or -D-glucose attain is +52.7º.

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37.(C) This problem can be solved by using the concept of stability of carbocation and S N 1 reaction.
When two phenyl groups are replaced by two para methoxy phenyl group, carbocation formed will be
more stable. As the stability of carbocation formed increases, rate of acidic hydrolysis increases:

Hence, (C) is the correct choice

38.(B)

39.(C) Correct option (C)

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

41.(B)

42.(C)

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43.(B)

44.(3) Only C1 and C2 are involved in osazone formation. Hence, aldohexoses and ketohexoses, which have
the same configurations at C3, C4 and C5 give the same osazone.
CH2OH
CHO CHO CO
H OH HO H
HO H
HO H HO H
H OH H OH H OH
H OH H OH H OH
CH2OH CH2OH CH2OH
Dglucose Dmannose Dfructose

45.(A)

Although both reactions are giving the same product, carbocation I is more stable than II.

46.(D) The time taken for the completion of 50% of reaction is same, implies that the reaction is first-order
type. This is possible when the halide undergoes S N1 reaction & for that the halide must be tertiary.

24
47.(B) 48.(3) pI  3
2

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49.(D) 2-methyl propan-2-ol is a tertiary alcohol, will react fastest with Lucas reagent:

50.(A) CH3OH is a polar protic solvent, promoting SN1 reaction.

51.(A) 52.(3)

53.(D) This problem can be solved by using the concept of synthesis of dye using electrophilic aromatic
substitution reaction. In basic (alkaline) solution naphthol exists as naphthoxide ion which is a strong o,
p-directing group.

Thus formation of dye can be shown as

Thus, (D) is the correct choice

54.(D) I & III are 2º & 1º carbocation also stabilized by lone pair delocalization of O, out of which I is more
stable than III. II & IV are simple 2º & 1º carbocations, respectively, of which II is more stable due to
greater hyper conjugation.
 The correct order is (I) > (III) > (II) > (IV)

55.(B) In orthophosphorous and pyrophosphorous acids, oxidation number of P is  3

56.(A)

S N 2 reaction bring about inversion of configuration.

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57.(B) The rate of SN2 reaction can increase with the increase in polarity of solvent only when the substrate &
nucleophile are both neutral (uncharged).

58.(C)

59.(A) C6H5OH  C2H5O 

C6H5O 
C2H5I
C6H5 — OC2H5

60.(6)

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61.(D)

CH2
Mg
62.(A) 63.(C) Br–CH2–CH2–CH2–Br CH2–CH2

64.(A) Pb(NO3 )2   PbO  NO2  O2

LiNO3 
 Li2O  NO2  O2

NaNO3 
 NaNO2  O2

NH4 NO2 
 N2  H2 O

65.(B) (Benzyne mechanism)

66.(ABD)
Aqua regia produces AuCl4 , PtCl62 with Au & Pt respectively and NO is liberated.

67.(B)


68.(D) X e[PtF6 ] 

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69.(A)

Reaction will take placed according to more activating group.

70.(C) 71.(B)

72.(CD) R : H 2SO 4 G : Br 2
H 2SO 4 is dehydrating in nature

73.(C)

74.(BC)
PCl5 (s) : [PCl4 ][PCl6 ]
PBr 5 (s) : [PBr 4 ][Br  ]

 Br 
Br2
75.(D) 3Br2  2Fe 
 2FeBr3 

Product

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