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.

     

(1)

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.

     

(4)

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

     

(1)

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.

 



Q 4 :    

Which among the following halide/s will not show SN1 reaction:                                    [2024]

Choose the most appropriate answer from the options given below:

  • (A), (B) and (D) only

     

  • (A) and (B) only

     

  • (B) and (C) only

     

  • (B) only

     

(4)

Vinyl carbocation is unstable as it has positive charge on sp hybridized carbon. Hence, its formation is difficult and vinyl halides do not show SN1 reaction.

Vinyl, aryl and halides with halogen at the bridgehead position neither show SN1 nor SN2 reactions.

 



Q 5 :    

Alkyl halide is converted into alkyl isocyanide by reaction with:                       [2024]

  • NaCN

     

  • AgCN

     

  • NH4CN

     

  • KCN

     

(2)

 



Q 6 :    

The product (C) in the below-mentioned reaction is:                     [2024]

  • Propene

     

  • Propan-2-ol

     

  • Propyne

     

  • Propan-1-ol

     

(2)

 



Q 7 :    

Given below are two statements: one is labelled as Assertion (A) and the other is labelled as Reason (R).                                             [2024]
Assertion (A): Haloalkanes react with KCN to form alkyl cyanides as a main product while with AgCN form isocyanide as the main product.

Reason (R): KCN and AgCN both are highly ionic compounds.

In the light of the above statements, choose the most appropriate answer from the options given below:

  • (A) is correct but (R) is not correct

     

  • Both (A) and (R) are correct but (R) is not the correct explanation of (A)

     

  • (A) is not correct but (R) is correct

     

  • Both (A) and (R) are correct and (R) is the correct explanation of (A)

     

(1)

KCN is an ionic compound and predominantly exists as K+ and CN-. In CN- both C and N have lone pairs (CN)(-) and can participate in nucleophilic substitution reactions with haloalkanes. But C donates its lone pair in preference to N and cyanide is formed as chief product.

AgCN is a covalent compound; hence, carbon does not have a free lone pair to react (Ag-CN). As only nitrogen has a lone pair, it reacts with haloalkanes to form isocyanides.

 



Q 8 :    

Identify the correct set of reagents or reaction conditions 'X' and 'Y' in the following set of transformation.                 [2024]

  • X = dil. aq. NaOH, 20°C, Y = Br2/CHCl3

     

  • X = conc. alc. NaOH, 80°C, Y = HBr/acetic acid

     

  • X = dil. aq. NaOH, 20°C, Y = HBr/acetic acid

     

  • X = conc. alc. NaOH, 80°C, Y = Br2/CHCl3

     

(2)

aq. NaOH causes substitution and alc. NaOH causes elimination.

 



Q 9 :    

Product P is                                                                    [2024]

  •  

  •  

  •  

  •  

(2)

 



Q 10 :    

Identify the major product in the following reaction.                                     [2024]

  •  

  •  

  •  

  •  

(4)