Q 1 :    

The correct statement regarding nucleophilic substitution reaction in a chiral alkyl halide is:                   [2024]

  • Racemisation occurs in SN1 reaction and inversion occurs in SN2 reaction.

     

  • Racemisation occurs in SN1 reaction and retention occurs in SN2 reaction.

     

  • Retention occurs in SN1 reaction and inversion occurs in SN2 reaction.

     

  • Racemisation occurs in both SN1 and SN2 reactions.

     

(A)

In SN1 reaction, carbocation is formed as an intermediate. Carbocation is planar and nucleophile may attack from either side of the plane. This gives a pair of enantiomers as reaction products i.e. product is racemic mixture. Although amount of inversion product is more than that of retention product because nucleophile starts attacking from back side even before leaving group has completely left the carbon. So in SN1 there is partial racemization.

In SN2, there is 100% inversion because nucleophile attacks from the side opposite to leaving group.

 



Q 2 :    

Given below are two statements:

 

Statement-I: High concentration of strong nucleophilic reagent with secondary alkyl halides which do not have bulky substituents will follow SN2 mechanism.

 

Statement-II: A secondary alkyl halide when treated with a large excess of ethanol follows SN1 mechanism.

 

In the light of the above statements, choose the most appropriate from the options given below:                      [2024]

  • Statement I is true but Statement II is false.

     

  • Statement I is false but Statement II is true.

     

  • Both Statement I and Statement II are false.

     

  • Both Statement I and Statement II are true.

     

(D)

Secondary alkyl halide follows both SN1 and SN2 paths parallelly. Out of SN1 and SN2, which one is preferred path by secondary alkyl halide depends upon other conditions such as strength of nucleophile and nature of solvent. Strong nucleophiles such as alkoxides and polar aprotic solvents such as DMF and DMSO prefer to keep the reaction along SN2 pathway. Weak nucleophiles such as water, alcohols and acetic acid and polar protic solvents such as water and alcohols (these are solvents as well as nucleophiles), prefer to keep the reaction along SN1 pathway.

 



Q 3 :    

Given below are two statements:

 

Statement (I): SN2 reactions are 'stereospecific', indicating that they result in the formation of only one stereo-isomer as the product.

 

Statement (II): SN1 reactions generally result in formation of product as racemic mixtures.

 

In the light of the above statements, choose the correct answer from the options given below:                    [2024]

  • Both Statement I and Statement II are true

     

  • Statement I is false but Statement II is true

     

  • Both Statement I and Statement II are false

     

  • Statement I is true but Statement II is false

     

(A)

Stereospecific reactions are those reactions for which if stereochemistry of reactants is changed, then major product formed is changed. In SN2 reactions, inversion occurs, so different stereoisomers give different products. Hence SN2 reactions are stereospecific.

In SN1 reactions, carbocation is formed as intermediate. Carbocation is planar hence nucleophile can attack from either side of the planar carbocation. This results in racemic mixture in products.