Question

How would you differentiates between SN1 and SN2 mechanisms of substitution reactions? give one example of each

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Answer 1

The SN1 and SN2 reactions are nucleophilic substitution reactions and most commonly found in Organic Chemistry. The two symbols SN1 and SN2 refer to two reaction mechanisms. The symbol SN stands for “nucleophilic substitution”. Even though both SN1 and SN2 are in the same category, they have many differences including the reaction mechanism, nucleophiles and solvents participated in the reaction, and the factors affecting the rate determining step. The key difference between SN1 and SN2 reactions is that SN1 reactions have several steps whereas SN2 reactions have only one step.

Nucleophile:

SN1 Reactions: SN1reactions require weak nucleophiles; they are neutral solvents such as CH3OH, H2O, and CH3CH2OH.

SN2 Reactions: SN2 reactions require strong nucleophiles. In other words, they are negatively charged nucleophiles such asCH3O–, CN–, RS–, N3– and HO–.

Solvent:

SN1 Reactions: SN1 reactions are favoured by polar protic solvents. Examples are water, alcohols, and carboxylic acids. They can also act as the nucleophiles for the reaction.

SN2 Reactions: SN2 reactions proceed well in polar aprotic solvents such as acetone, DMSO, and acetonitrile.

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Answer 2

Explanation:

SN1 Reaction:

• SN1 reaction is a unimolecular reaction.
• SN1 reaction follows first order kinetics.
• SN1 reaction is a process of two steps.
• SN1 reaction leads to carbonation formation.
• In SN1 reaction, order of reactivity is as follows. 3° > 2° > 1°
• In SN1 reaction, racemisation takes place.
• Example: Hydrolysis of tert-butyl bromide with aqueous NaOH solution

SN2 Reaction:

• SN2 reaction is a bimolecular reaction.
• SN2 reaction follows second order kinetics.
• SN2 reaction is a process of one step.
• SN2 reaction does not leads to carbonation formation.
• In SN2 reaction, order of reactivity is as follows. 1° > 2° > 3°
• In SN2 reaction, inversion of configuration takes place.
• Example: Walden inversion where an asymmetric carbon atom undergoes inversion of configuration.

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