Question
Question: Which of the following factors does not favour \({S_N}1\) mechanism? A. Strong nucleophile B. Po...
Which of the following factors does not favour SN1 mechanism?
A. Strong nucleophile
B. Polar solvent
C. Low conc. of nucleophile
D. 3rd halide
Solution
We know that SN1 stands for nucleophilic substitution and 1 represents unimolecular rate determining step of this mechanism. The mechanism of SN1 generally has two steps. One of the examples of SN1 mechanism is the hydrolysis reaction of tert-butyl bromide producing tert-butanol. In inorganic chemistry, SN1 reaction is called a dissociative mechanism.
Complete step by step answer: We must remember that the SN1 reactions form a carbocation intermediate. The reaction of tertiary alkyl halides under strongly basic (or) acidic conditions to form tertiary alcohols is SN1 reaction.
We know that the SN1 mechanism goes stepwise. The leaving group leaves, and the formation of carbocation that is attacked by the nucleophile.
In SN1 reaction, carbocation stability is the big barrier. The stability of the carbocation increases with increasing carbon substitution (tertiary>secondary>>primary) as well as with resonance. The loss of leaving group of SN1 reaction gives carbocation, the reaction rate would be proportional carbocation stability. Since stability of carbon increases as we move from primary to secondary to tertiary. The reaction rate moves from primary (slowest)<SN1 proceed with weak nucleophiles. Option (C) is correct because weak nucleophiles only favour SN1 mechanism and strong nucleophiles do not favour SN1 mechanism. Strong nucleophiles favour SN2 mechanism.
SN1 proceed with polar protic solvents like water, carboxylic acids, and alcohols. The polar solvent increases the carbocation stability and they both favor SN1 mechanism. Therefore, Option (B) is incorrect.
SN1 proceeds with strong nucleophiles that have low concentration. So, Option (A) is incorrect.
SN1 reaction would be more favoured if the leaving group is bonded to tertiary, allylic (or) benzylic carbon, the intermediate carbocation would be more stable. Only tertiary halides undergo SN1 mechanism.
So, the correct answer is “Option D”.
Note:
One should not confuse them with polar solvents used in SN1 and SN2 reactions. In SN1 reaction, polar protic solvent is required and in SN2 reactions polar aprotic solvent is required. Elimination reactions and carbocation rearrangements are the two common side reactions that happen. SN1 follows first order kinetic reaction and is multistep reactions.