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Jee 2022, 100Q, Advanced Sprint, Organic Chemistry

The document contains multiple chemistry problems and their solutions. A reaction is described, and students are asked to identify an incorrect statement about the products. The answer is that statement B is incorrect, as it describes positional isomerism which does not apply in this case. Similarly, other problems assess understanding of concepts like stereochemistry, organic reactions, and reaction mechanisms. The number of problems solved is not provided.
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0% found this document useful (0 votes)
210 views70 pages

Jee 2022, 100Q, Advanced Sprint, Organic Chemistry

The document contains multiple chemistry problems and their solutions. A reaction is described, and students are asked to identify an incorrect statement about the products. The answer is that statement B is incorrect, as it describes positional isomerism which does not apply in this case. Similarly, other problems assess understanding of concepts like stereochemistry, organic reactions, and reaction mechanisms. The number of problems solved is not provided.
Copyright
© © All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
Available Formats
Download as PDF, TXT or read online on Scribd
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Consider the following reaction.

Identify the incorrect statement. (x and y are the major


products)

A x shows geometrical isomerism

B y shows positional isomerism

D
Consider the following reaction.

Identify the incorrect statement. (x and y are the major


products)

A x shows geometrical isomerism

B y shows positional isomerism

D
Solution:

(D)
Consider the following compound

The absolute configuration of C* and C# carbon atoms


respectively are

A R, S

B S, S

C S, R

D R, R
Consider the following compound

The absolute configuration of C* and C# carbon atoms


respectively are

A R, S

B S, S

C S, R

D R, R
Solution:

(D)
Consider the following compounds and their reaction with aq.
HNO2.

Identify the correct statement.

A I and III will give same compound

B I and IV will give same compound

C I and II will give same compound

D II and III will give same compound


Consider the following compounds and their reaction with aq.
HNO2.

Identify the correct statement.

A I and III will give same compound

B I and IV will give same compound

C I and II will give same compound

D II and III will give same compound


Solution:

(C)
Consider the following reaction.

The major products during the reaction is (are)

A Ethane

B Methane

D
Consider the following reaction.

The major products during the reaction is (are)

A Ethane

B Methane

D
Solution:

(A, C)
Consider the following compound.

How many monochloro derivatives are possible if given


compound is treated with Cl2/hv (excluding stereoisomers)?
Solution:

(01)
Column-I contains some transformations and Column-II contains
reagents required for that particular transformation. (Consider aldol
condensation only in basic medium). Match Column-I and Column-II.
A A → (P, Q, R), B → (P, R, S), C → (P), D → (T)

B A → (P, Q), B → (P, S), C → (P), D → (T)

C A → (P, R), B → (P, R, S), C → (P), D → (T)

D A → (P, Q, R), B → (P, S), C → (P), D → (T)


A A → (P, Q, R), B → (P, R, S), C → (P), D → (T)

B A → (P, Q), B → (P, S), C → (P), D → (T)

C A → (P, R), B → (P, R, S), C → (P), D → (T)

D A → (P, Q, R), B → (P, S), C → (P), D → (T)


Solution:

A (P, Q, R); B (P, R, S); C (P); D(T)


In the Wittig reaction, the conversion of a carbonyl compound
to give an alkene is done with phosphorus ylide. Consider the
reaction sequence.

The correct statements among the following are

BuLi extracts a proton from


A
sp3 hybridised carbon

B X is CH2 = P(Ph)3

D Z is O = P(Ph)3
In the Wittig reaction, the conversion of a carbonyl compound
to give an alkene is done with phosphorus ylide. Consider the
reaction sequence.

The correct statements among the following are

BuLi extracts a proton from


A
sp3 hybridised carbon

B X is CH2 = P(Ph)3

D Z is O = P(Ph)3
Solution:

(A, B, C, D)
Which of the following compound(s) give(s) different products
by SN1 and SN2 mechanism?
(Consider stereoisomers to be different products)

A B

C D
Which of the following compound(s) give(s) different products
by SN1 and SN2 mechanism?
(Consider stereoisomers to be different products)

A B

C D
Solution:

(A, B, D)
Both the following compounds (P) and (Q) undergo base
induced elimination of HBr to form the same product (R).

Which of the following statements is true?

A (P) reacts faster than (Q)

B (Q) reacts faster than (P)

Both (P) and (Q) react at


C
the same rate
Data is insufficient to
D
make the predictions
Both the following compounds (P) and (Q) undergo base
induced elimination of HBr to form the same product (R).

Which of the following statements is true?

A (P) reacts faster than (Q)

B (Q) reacts faster than (P)

Both (P) and (Q) react at


C
the same rate
Data is insufficient to
D
make the predictions
Solution:

(B)
How many pair of diastereomers of (P) are possible?

A 5

B 7

C 6

D 4
How many pair of diastereomers of (P) are possible?

A 5

B 7

C 6

D 4
Solution:

(D)
How many optical isomers of (Q) are possible?

A 7

B 6

C 5

D 4
How many optical isomers of (Q) are possible?

A 7

B 6

C 5

D 4
Solution:

(D)

Compound (Q) has two chiral centres.

No. of optical isomers = 2n


(for unsymmetrical molecule) = 2n = 4
What is the structure of (R)?

A Ph - CD = CH - CH3

B Ph - CHD - CH = CH2

C Ph - CH = CH - CH3

D Ph - CH2 - CD = CH2
What is the structure of (R)?

A Ph - CD = CH - CH3

B Ph - CHD - CH = CH2

C Ph - CH = CH - CH3

D Ph - CH2 - CD = CH2
Solution:

(A)

Saytzeff elimination.

R is Ph - CD = CH - CH3
Consider the following reaction sequence.

The number of 6 membered rings in product (P) is x, the


number of moles of Grignard reagent that can react with one
mole of product (P) is y. The value of x + y is
Solution:

(1)

x=1
Grignard reagent will not interact with product.
When phthalic acid react with excess of NH3 and then strongly
heated, it forms a compound X. X on reaction with 2-
chloroethanamine in presence of base follows ‘n’ order kinetics
for nucleophilic substitution and give a compound y. After the
hydrolysis of y in acidic medium, phthalic acid is obtained
along with compound Z.
The number of nitrogen atoms present in 1 molecule of X and Z
is x’ and z’ respectively. Find value of (x’ + z’ + n).
Solution:

(5)
Consider the following reaction procedure.

Which of the following statement(s) is/are incorrect?

A P1 has two alkoxy groups

B P2 has two carboxy groups

C P3 has one ester group

D P2 is 2-methoxybenzoic acid
Consider the following reaction procedure.

Which of the following statement(s) is/are incorrect?

A P1 has two alkoxy groups

B P2 has two carboxy groups

C P3 has one ester group

D P2 is 2-methoxybenzoic acid
Solution:

(A), (B), (D)

Ether do not undergo oxidation and in alkaline medium there is no


hydrolysis that can occur on ether linkage.
Consider the following reaction.
14

The mass of oxygen present in one mole of T (T is an aromatic


compound) is x g. Calculate the value of x/6.
Solution:

(3)
Identify the reaction which will finally produce an aromatic
compound.

D
Identify the reaction which will finally produce an aromatic
compound.

D
Solution:

(B), (D)
Solution:

(B), (D)
The unknown alcohol ‘X’ which is used in the above conversion
is

A 2-Methylbutan-2-ol

B 3-Methyl-2-methylbutan-2-ol

C 2-Methylpentan-2-ol

D 3-Methyl-2-methylpentan-2-ol
The unknown alcohol ‘X’ which is used in the above conversion
is

A 2-Methylbutan-2-ol

B 3-Methyl-2-methylbutan-2-ol

C 2-Methylpentan-2-ol

D 3-Methyl-2-methylpentan-2-ol
Solution:
Identify the statement(s) which is/are correct.

A R and S can be distinguished


by Tollen’s test

B The reagent ‘V’ can be KOI/KOH

C Molar mass of the salt T is 84 g/mol

D Compound Q has two geometrical isomers


Identify the statement(s) which is/are correct.

A R and S can be distinguished


by Tollen’s test

B The reagent ‘V’ can be KOI/KOH

C Molar mass of the salt T is 84 g/mol

D Compound Q has two geometrical isomers


Solution:

(A), (B), (C)


The aliphatic aldehyde P and Q react in the presence of aq
K2CO3 to give a compound R. R upon treatment with KCN forms
compound S. On acidification and heating ‘S’ gives the product
shown below
The correct structural formula of compound S is

A B

C D
The correct structural formula of compound S is

A B

C D
Solution:
How many salt show higher rate of decarboxylation than
when heated with soda lime ?
Solution:

(6)

α- Cyano, malonic acid, β - keto acid and β - 𝛾 - unsaturated salt or acid


show very high rate of reaction.
In the given compounds

The total number of aromatic compounds is ‘x’. Find the value


of x.
Solution:

(4)

10 - Annulene is non aromatic

(i), (iv), (v) and (viii) are aromatic according to Huckel’s rule
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