Q.

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]

1 Statement I is true but Statement II is false.  
2 Statement I is false but Statement II is true.  
3 Both Statement I and Statement II are false.  
4 Both Statement I and Statement II are true.  

Ans.

(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.