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Test: SN2 Reaction Reactivity - NEET MCQ


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25 Questions MCQ Test - Test: SN2 Reaction Reactivity

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Test: SN2 Reaction Reactivity - Question 1

Only One Option Correct Type

Direction (Q. Nos. 1-12) This section contains 12 multiple choice questions. Each question has four choices (a), (b), (c))and (d), out of which ONLY ONE is correct.

Q. 

Which of the following would be the strongest nucleophile in methanol?

Detailed Solution for Test: SN2 Reaction Reactivity - Question 1

Nucleophilicity increases down the group in hydroxylic solvents.

Test: SN2 Reaction Reactivity - Question 2

Predict the product in nucleophilic substitution reaction.

Detailed Solution for Test: SN2 Reaction Reactivity - Question 2

Inversion of configuration takes place at chiral carbon.

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Test: SN2 Reaction Reactivity - Question 3

What is the product of the given reaction?

Detailed Solution for Test: SN2 Reaction Reactivity - Question 3

 attack at less substituted carbon of epoxide ring from the side opposite to — CH3 group.

Test: SN2 Reaction Reactivity - Question 4

Which is the product of the given reaction?

Detailed Solution for Test: SN2 Reaction Reactivity - Question 4


Test: SN2 Reaction Reactivity - Question 5

What is the major product of the given reaction ?

Detailed Solution for Test: SN2 Reaction Reactivity - Question 5

α-carbon is achiral, hence retention of configuration at β-carbon.

Test: SN2 Reaction Reactivity - Question 6

Which of the following are the examples of strong nucleophiles but weak base in protic solvents?

I. CH3S-
II. CH3O-
III. I-
IV. H2O
V. F-

Detailed Solution for Test: SN2 Reaction Reactivity - Question 6

Both CH3S- and I- are weak bases but strong nucleophiles.

Test: SN2 Reaction Reactivity - Question 7

The specific rotation of optically pure (R)-2- butanol is -13.52° at 25°C. An optically pure sample of (R)-2- bromobutane was treated with aqueous NaOH in order to form 2-butanol via SN2 reaction. What would be the specific rotation of the product assuming 100% yield?

Detailed Solution for Test: SN2 Reaction Reactivity - Question 7

(S)-2-butanol is formed with specific rotation + 13.52°.

Test: SN2 Reaction Reactivity - Question 8

Which of the following correctly describe the relative nucleophilicities of methoxide and tertiary butoxide ion?

Detailed Solution for Test: SN2 Reaction Reactivity - Question 8

Although CH3O- is weaker base than (CH3)3CO- , former is stronger nucleophile due to smaller size.

Test: SN2 Reaction Reactivity - Question 9

Arrange the following in increasing order of reactivity in an SN2 reaction with K I in acetone solvent.

Detailed Solution for Test: SN2 Reaction Reactivity - Question 9

In halogen-exchange (Finkelstein reaction), reactivity is determined by solubility of Na X formed in acetone. Lower the solubility of Na X in acetone, easier the reaction. NaCI is less soluble than NaBr in acetone.

Test: SN2 Reaction Reactivity - Question 10

In the following set of nucleophiles, the strongest and the weakest nucleophile respectively are

I. CH3S-
II. CH3COC-
III. HO-
IV. C6H5C-

Detailed Solution for Test: SN2 Reaction Reactivity - Question 10

CH3S-(I) is strongest nucleophile and C6H5O-(IV) is weakest due to resonance stabilisation in it.

Test: SN2 Reaction Reactivity - Question 11

The major product of the following reaction is:

Detailed Solution for Test: SN2 Reaction Reactivity - Question 11

Test: SN2 Reaction Reactivity - Question 12

Which of the following on treatment with NaCN (aq) results in an achiral product?

Detailed Solution for Test: SN2 Reaction Reactivity - Question 12

*Multiple options can be correct
Test: SN2 Reaction Reactivity - Question 13

One or More than One Options Correct Type

Direction (Q. Nos. 13-17) This section contains 5 multiple choice questions. Each question has four choices (a), (b), (c) and (d), out of which ONE or MORE THAN ONE are correct.

Q. 

In which of the following pair(s), the first one is stronger nucleophile than the second one?

Detailed Solution for Test: SN2 Reaction Reactivity - Question 13

CH3O- is stronger nucleophile (smaller size) than (CH3)3CO-. HS- is stronger nucleophile than HO- as S is more polarisable than O.

*Multiple options can be correct
Test: SN2 Reaction Reactivity - Question 14

In which of the following pair(s), the first one is better leaving group than the second one?

Detailed Solution for Test: SN2 Reaction Reactivity - Question 14

Both   are weaker base than its other counterpart.

*Multiple options can be correct
Test: SN2 Reaction Reactivity - Question 15

In which of the following reaction, inversion of configuration at chiral carbon takes place?

Detailed Solution for Test: SN2 Reaction Reactivity - Question 15

In both option (a) and option (d) α-carbon is chiral, hence SN2 reaction will lead to inversion of configuration. In option (b), α-carbon is achiral, configuration of chiral β-carbon will not be affected. In option (c) SN2 reaction occur twice at the same a-carbon hence, double inversion will give net retention of configuration.

*Multiple options can be correct
Test: SN2 Reaction Reactivity - Question 16

Consider the following SN2 reaction,

1-bromobutane + NaCN(aq) → pentanenitrile +NaBr

Q.

Which of the following solvents) when replaces water in the above reaction, increases the rate?

Detailed Solution for Test: SN2 Reaction Reactivity - Question 16

All the mentioned solvents are polar and'aprotic, hence increases rate of SN2 reaction.

*Multiple options can be correct
Test: SN2 Reaction Reactivity - Question 17

In which of the following reaction(s), reactant and product are correctly matched?

Detailed Solution for Test: SN2 Reaction Reactivity - Question 17

In both option (a) and option (c) products have inverted configuration but at α-carbon only. In option (b) product has inverted configuration at both α and β-carbons, hence not true in SN2 reaction. In case of option (d), an equilibrium will be established with K = 1.


At equilibrium both enantiomers exist in equal amounts giving racemic mixture.

Test: SN2 Reaction Reactivity - Question 18

Comprehension Type

Direction (Q. Nos. 18-23) This section contains 2 paragraphs, each describing theory, experiments, data, etc. Six questions related to the paragraphs have been given. Each question has only one correct answer among the four given options (a), (b), (c) and (d).

Passage I

In a SN2 reaction, solvent plays a very important role. Hydroxylic solvents like water, alcohols, carboxylic acids etc., solvate nucleophile, decreases its reactivity in the reaction.
Size of donor atom of nucleophile also affect nucleophilicity. A larger donor atom is more easily polarised and less solvated, hence a stronger nucleophile. Therefore, in a given group of periodic table, nucleophilicity increases down the group. However solvation effect is more predominant than polarisability.

Q. 

In water, the order of nucleophilicity of halides is

Detailed Solution for Test: SN2 Reaction Reactivity - Question 18

F- is most hydrated, least nucleophilic and I- is most polarisable, strongest nucleophile among halides in H2O.

Test: SN2 Reaction Reactivity - Question 19

Passage I

In a SN2 reaction, solvent plays a very important role. Hydroxylic solvents like water, alcohols, carboxylic acids etc., solvate nucleophile, decreases its reactivity in the reaction.
Size of donor atom of nucleophile also affect nucleophilicity. A larger donor atom is more easily polarised and less solvated, hence a stronger nucleophile. Therefore, in a given group of periodic table, nucleophilicity increases down the group. However solvation effect is more predominant than polarisability.

Q. 

In dimethyl sulphoxide (DMSO) solvent, the order of nucleophilicity of haiides ion is

Detailed Solution for Test: SN2 Reaction Reactivity - Question 19

In polar aprotic solvent, basicity parallels nucleophilicity.

Test: SN2 Reaction Reactivity - Question 20

Passage I

In a SN2 reaction, solvent plays a very important role. Hydroxylic solvents like water, alcohols, carboxylic acids etc., solvate nucleophile, decreases its reactivity in the reaction.
Size of donor atom of nucleophile also affect nucleophilicity. A larger donor atom is more easily polarised and less solvated, hence a stronger nucleophile. Therefore, in a given group of periodic table, nucleophilicity increases down the group. However solvation effect is more predominant than polarisability.

Q. 

Which of the following describe correctly the role of H2O a s solvent in a SN2 reaction?

Detailed Solution for Test: SN2 Reaction Reactivity - Question 20

Hydroxylic solvents like H2O , stabilises both nucleophile and transition state, but to a greater extent to nucleophile. As a result, activation energy increases and rate of reaction decreases.

Test: SN2 Reaction Reactivity - Question 21

Passage II

In a SN2 reaction, back side attack takes place which leads to inversion of configuration ata-carbon which is known as Walden’s inversion :

Q. 

What is true regarding the follow ing reaction? 

Detailed Solution for Test: SN2 Reaction Reactivity - Question 21

The product would have opposite configuration at a-carbon, but reactants and products are not isomers, they are different compounds, have their characteric stereochemical properties not inter-related.

Test: SN2 Reaction Reactivity - Question 22

Passage II

In a SN2 reaction, back side attack takes place which leads to inversion of configuration ata-carbon which is known as Walden’s inversion :

Q. 

What can be correctly predicted regarding product of the following reaction ?

Detailed Solution for Test: SN2 Reaction Reactivity - Question 22

Both Cl can act as leaving group and there will be equal probability of the two chlorides to leave, giving racemic mixture of products.

Test: SN2 Reaction Reactivity - Question 23

Passage II

In a SN2 reaction, back side attack takes place which leads to inversion of configuration ata-carbon which is known as Walden’s inversion :

Q. 

What can be predicted correctly about product of the following SN2 reaction?

Detailed Solution for Test: SN2 Reaction Reactivity - Question 23

*Answer can only contain numeric values
Test: SN2 Reaction Reactivity - Question 24

One Integer Value Correct Type

Direction (Q. Nos. 24 and 25) This section contains 2 questions. When worked out will result in an integer from 0 to 9 {both inclusive).

Q. 

How many of the following reactions fail to give major product by SN2 reaction as indicated?

 


v . H—C≡C—CH2—CH2I + CH3MgBr → H—C ≡C— CH2— CH2— CH3


Detailed Solution for Test: SN2 Reaction Reactivity - Question 24

In (iii), (iv), (v) and (ix); Neutralisation will be preferred over SN2 reaction. In (vi), due to tertiary α-carbon, SN2 is very difficult, however E2 elimination reaction will be preferred in this case.

*Answer can only contain numeric values
Test: SN2 Reaction Reactivity - Question 25

In the following reaction,

Q.

How many different dicyano products are expected?


Detailed Solution for Test: SN2 Reaction Reactivity - Question 25

Any of the two Cl can be substituted by CN- as:


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