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Test: SN1 & SN2 Reactions(17 Nov) - JEE MCQ


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10 Questions MCQ Test - Test: SN1 & SN2 Reactions(17 Nov)

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*Multiple options can be correct
Test: SN1 & SN2 Reactions(17 Nov) - Question 1

Which of the following can catalyse the following SN1 reaction?

Detailed Solution for Test: SN1 & SN2 Reactions(17 Nov) - Question 1

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:

Test: SN1 & SN2 Reactions(17 Nov) - Question 2

Comprehension Type

Direction (Q. Nos. 23-27) 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 C7H13Br. A undergoes very fast SN1 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 SN1 reaction and produces two principal products B and C. Both B and C are alcohols with their molecular formula C7H14O. 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?

Detailed Solution for Test: SN1 & SN2 Reactions(17 Nov) - Question 2

It shows geometrical isomerism as well as it has a chiral carbon. Hence, A will have four stereoisomers

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Test: SN1 & SN2 Reactions(17 Nov) - Question 3

A chemist isolated a compound A with molecular formula C7H13Br. A undergoes very fast SN1 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 SN1 reaction and produces two principal products B and C. Both B and C are alcohols with their molecular formula C7H14O. 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 ?

Detailed Solution for Test: SN1 & SN2 Reactions(17 Nov) - Question 3

 Alcohols B and C are: 


Both S and C have one chiral carbon each, both show optical isomerism.

Test: SN1 & SN2 Reactions(17 Nov) - Question 4

A chemist isolated a compound A with molecular formula C7H13Br. A undergoes very fast SN1 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 SN1 reaction and produces two principal products B and C. Both B and C are alcohols with their molecular formula C7H14O. 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?

Detailed Solution for Test: SN1 & SN2 Reactions(17 Nov) - Question 4

It has three chiral carbon, hence eight stereoisomers.

Test: SN1 & SN2 Reactions(17 Nov) - Question 5

A chemist isolated a compound A with molecular formula C7H13Br. A undergoes very fast SN1 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 SN1 reaction and produces two principal products B and C. Both B and C are alcohols with their molecular formula C7H14O. 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(C7H14) would be produced. How many different structure(s) can be drawn for this D ?

Detailed Solution for Test: SN1 & SN2 Reactions(17 Nov) - Question 5

Test: SN1 & SN2 Reactions(17 Nov) - Question 6

A chemist isolated a compound A with molecular formula C7H13Br. A undergoes very fast SN1 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 SN1 reaction and produces two principal products B and C. Both B and C are alcohols with their molecular formula C7H14O. 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 (C7H12) is produced as major product by E2 elimination reaction. Which of the following statement will be consistent with E?

Detailed Solution for Test: SN1 & SN2 Reactions(17 Nov) - Question 6

Test: SN1 & SN2 Reactions(17 Nov) - Question 7

A correct statement about transition state of SN2 reaction is 

Detailed Solution for Test: SN1 & SN2 Reactions(17 Nov) - Question 7

SN2 reaction is a one step (concerted) reaction that involes a single transition state.

Test: SN1 & SN2 Reactions(17 Nov) - Question 8

What is the correct increasing order of reactivity of the  followings in SN2 reaction ?

I. CH2 = CHCH2 — Br
II. CH2 = CH— I
III. CH3CH2CH2 — I
IV. CH3OCH2CH2 — I 

Detailed Solution for Test: SN1 & SN2 Reactions(17 Nov) - Question 8

Allyl bromide (I) is most reactive among the given halides as pi bonds from allylic position stabilises the transition state. Vinyl iodide (II) is least reactive due to partial double bond character. Electron withdrawing inductive effect of CH3O- increases reactivity of (IV) over (III)

Test: SN1 & SN2 Reactions(17 Nov) - Question 9

What is the correct increasing order of reactivity of the following in the SN2 reaction?

Detailed Solution for Test: SN1 & SN2 Reactions(17 Nov) - Question 9

 (IV) is most reactive as it is benzylic as well as electron withdrawing effect of — NO2 further increases the reactivity. (Ill) is least reactive due to resonance effect resulting in partial double bond character between carbon and chlorine. (I) is less reactive in SN2 reaction than II, due to greater steric hindrance in (I).

Test: SN1 & SN2 Reactions(17 Nov) - Question 10

Consider the two lines shown in the diagram given below.

Q. 

In a SN2 reaction, these two lines compare the effect of the

Detailed Solution for Test: SN1 & SN2 Reactions(17 Nov) - Question 10

Substrates are same as they are at same potential energies. Nucleophiles are different as magnifested by different activation energies and different products with different potential energies,

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