What are SN1 and SN2 mechanisms? Discuss with examples of haloalkanes reacting with aqueous KOH.
Question
What are SN1 and SN2 mechanisms? Discuss with examples of haloalkanes reacting with aqueous KOH.
Solution
SN1 and SN2 are two different types of mechanisms that are used in organic chemistry for substitution reactions.
-
SN1 Mechanism: SN1 stands for Substitution Nucleophilic Unimolecular. In this mechanism, the rate of the reaction depends on the concentration of one reactant, hence the term 'unimolecular'. The reaction occurs in two steps:
- Step 1: The leaving group leaves, forming a carbocation intermediate.
- Step 2: The nucleophile attacks the carbocation and forms a new bond.
For example, if we take a haloalkane like 2-chloro-2-methylpropane and react it with aqueous KOH, the chlorine atom leaves first to form a carbocation. Then, the hydroxide ion (OH-) from KOH attacks the carbocation, resulting in 2-methylpropan-2-ol.
-
SN2 Mechanism: SN2 stands for Substitution Nucleophilic Bimolecular. In this mechanism, the rate of the reaction depends on the concentration of two reactants, hence the term 'bimolecular'. The reaction occurs in one step, where the nucleophile attacks the substrate and the leaving group leaves simultaneously.
For example, if we take a haloalkane like bromoethane and react it with aqueous KOH, the hydroxide ion (OH-) from KOH attacks the carbon atom bonded to the bromine atom, while the bromine atom leaves at the same time. This results in ethanol.
In both mechanisms, the nucleophile (OH- from KOH) replaces the halogen atom in the haloalkane. However, the rate and the steps of the reaction are different.
Similar Questions
Substitution Reactions:Explain the mechanism of nucleophilic substitution reactions (SN1 and SN2) in haloalkanes with suitable examples.
What is the stereochemistry of the product formed in an SN2 reaction involving a haloalkane? Provide an example
Describe the mechanism of elimination reactions (E1 and E2) in haloalkanes with examples.
Explain the difference between E1 and E2 reactions using examples of haloalkanes.
How does the reactivity of haloalkanes vary with the nature of the halogen atom?
Upgrade your grade with Knowee
Get personalized homework help. Review tough concepts in more detail, or go deeper into your topic by exploring other relevant questions.