Haloalkanes & Haloarenes Test

Result

Haloalkanes & Haloarenes Test - 9

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Weekly Quiz Competition

Question 1
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What is/are the expected solvolysis product(s) in the following reaction?

A

B

C

D
All are correct

Solution
Question 2
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Which of the following can catalyse the following S_N 1 reaction?

A
ZnCI₂

B
NaOH

C
AgNO₃

D
Option A,C are Correct

Solution

ZnCI₂ is a Lewis acid, helps in formation of carbocation. AgNO₃ form s AgCI precipitate, derive heterolysis reaction belo w in forward direction:

From the given information structure of A can be derived as:
Question 3
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Comprehension Type

Direction : This section contains a paragraph, describing theory, experiments, data, etc.
Five questions related to the paragraph have been given. Each question has only one correct answer among the four given options (a), (b), (c) and (d).

Passage

A chemist isolated a compound A with molecular formula C₇ H₁₃ Br. A undergoes very fast S_N 1 reaction. Spectroscopic evidence indicated that compound A has the following structural characteristics : It contains five sp³ -hybridised carbon atoms. Among those five sp³ carbon atoms, three are methyl groups, one CH₂ group and one CH group.
It also contains two sp² -hybridised carbon atoms. Also there is only one hydrogen atom attached to sp² carbons.
The compound contains a total of six aliylic hydrogen atoms.
The carbon atom that holds the Br has one H attached to it.
Working Space
When compound A reacts with boiling water, it undergoes a S_N 1 reaction and produces two principal products B and C. Both B and C are alcohols with their molecular formula C₇ H₁₄ O. Among the two alcohols, B has the —OH group attached to a sp³ carbon atom that has no H -atoms bonded to it.

Q.

How many stereoisomers are possible for A?

A
2

B
3

C
4

D
None of these

Solution

It shows geometrical isomerism as well as it has a chiral carbon. Hence, A will have four stereoisomers
Question 4
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A chemist isolated a compound A with molecular formula C₇ H₁₃ Br. A undergoes very fast S_N 1 reaction. Spectroscopic evidence indicated that compound A has the following structural characteristics : It contains five sp³ -hybridised carbon atoms. Among those five sp³ carbon atoms, three are methyl groups, one CH₂ group and one CH group.
It also contains two sp² -hybridised carbon atoms. Also there is only one hydrogen atom attached to sp² carbons.
The compound contains a total of six aliylic hydrogen atoms.
The carbon atom that holds the Br has one H attached to it.
Working Space
When compound A reacts with boiling water, it undergoes a S_N 1 reaction and produces two principal products B and C. Both B and C are alcohols with their molecular formula C₇ H₁₄ O. Among the two alcohols, B has the —OH group attached to a sp³ carbon atom that has no H -atoms bonded to it.

Q.

What can be said about the isomerism shown by the two alcohols B and C ?

A
Both B and C show stereoisomerism and can be resolved into enantiomers

B
B and C are stereoisomers

C
Both B and C show stereoisomerism but only C can be resolved into enantiomers

D
Neither B nor C can be resolved into enantiomers

Solution

Alcohols B and C are:

Both S and C have one chiral carbon each, both show optical isomerism.
Question 5
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A chemist isolated a compound A with molecular formula C₇ H₁₃ Br. A undergoes very fast S_N 1 reaction. Spectroscopic evidence indicated that compound A has the following structural characteristics : It contains five sp³ -hybridised carbon atoms. Among those five sp³ carbon atoms, three are methyl groups, one CH₂ group and one CH group.
It also contains two sp² -hybridised carbon atoms. Also there is only one hydrogen atom attached to sp² carbons.
The compound contains a total of six aliylic hydrogen atoms.
The carbon atom that holds the Br has one H attached to it.
Working Space
When compound A reacts with boiling water, it undergoes a S_N 1 reaction and produces two principal products B and C. Both B and C are alcohols with their molecular formula C₇ H₁₄ O. Among the two alcohols, B has the —OH group attached to a sp³ carbon atom that has no H -atoms bonded to it.

Q.

If the starting compound A is brominated in gas phase in the presence of a Lewis acid catalyst, a tribromide would result from addition of Br₂ to . How many different structures of stereoisomers can be drawn for this tribromide?

A
2

B
4

C
8

D
None of these

Solution

It has three chiral carbon, hence eight stereoisomers.
Question 6
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A chemist isolated a compound A with molecular formula C₇ H₁₃ Br. A undergoes very fast S_N 1 reaction. Spectroscopic evidence indicated that compound A has the following structural characteristics : It contains five sp³ -hybridised carbon atoms. Among those five sp³ carbon atoms, three are methyl groups, one CH₂ group and one CH group.
It also contains two sp² -hybridised carbon atoms. Also there is only one hydrogen atom attached to sp² carbons.
The compound contains a total of six aliylic hydrogen atoms.
The carbon atom that holds the Br has one H attached to it.
Working Space
When compound A reacts with boiling water, it undergoes a S_N 1 reaction and produces two principal products B and C. Both B and C are alcohols with their molecular formula C₇ H₁₄ O. Among the two alcohols, B has the —OH group attached to a sp³ carbon atom that has no H -atoms bonded to it.

Q.

If the original compound A is treated with LiAIH₄ a new compound D(C₇ H₁₄ ) would be produced. How many different structure(s) can be drawn for this D ?

A
1

B
2

C
3

D
4

Solution
Question 7
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A chemist isolated a compound A with molecular formula C₇ H₁₃ Br. A undergoes very fast S_N 1 reaction. Spectroscopic evidence indicated that compound A has the following structural characteristics : It contains five sp³ -hybridised carbon atoms. Among those five sp³ carbon atoms, three are methyl groups, one CH₂ group and one CH group.
It also contains two sp² -hybridised carbon atoms. Also there is only one hydrogen atom attached to sp² carbons.
The compound contains a total of six aliylic hydrogen atoms.
The carbon atom that holds the Br has one H attached to it.
Working Space
When compound A reacts with boiling water, it undergoes a S_N 1 reaction and produces two principal products B and C. Both B and C are alcohols with their molecular formula C₇ H₁₄ O. Among the two alcohols, B has the —OH group attached to a sp³ carbon atom that has no H -atoms bonded to it.

Q.

If the starting compound A is treated with ethanolic solution of KOH in boiling condition, a further new compound E (C₇ H₁₂ ) is produced as major product by E2 elimination reaction. Which of the following statement will be consistent with E?

A
It will have no stereogenic centre i.e. it will not show stereoisomerism

B
It will show stereoisomerism but cannot be resolved into enantiomers

C
It will have more than one stereogenic centres and more than two, different structures of stereoisomers can be drawn for E

D
None of the above appropriately applies to E

Solution
Question 8
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One Integer Value Correct Type

Direction : This section contains 3 questions. When worked out will result in an integer from 0 to 9 (both inclusive).

Consider the following solvolysis reaction.

Q.

How many principal products would be formed by S_N 1 reaction?

A
6

B
5

C
3

D
1

Solution
Question 9
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How many of the following undergo solvolysis reaction faster than benzyl chloride?

A
1

B
5

C
8

D
9

Solution

Only (iii), (iv), (v), (vi) and (viii) form carbocations more stable than benzyl carbocation.
Question 10
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Following compound when heated in ethanol, S_N 1 reaction occur involving rearrangement of carbocation.

Q.

In the major product, how many carbon atoms are present in the single largest ring?

A
9

B
8

C
6

D
5

Solution