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The hydrolysis of chloro-, iodo-, and bromoalkanes proceeds via an SN1 or SN2 mechanism, depending on the structure of the halogenoalkane and the reaction conditions.
SN1 (Substitution Nucleophilic Unimolecular)
Favored for tertiary halogenoalkanes and in polar protic solvents.
Involves a two-step process:
1. Formation of a carbocation: The carbon-halogen bond breaks heterolytically, forming a carbocation and a halide ion.
2. Nucleophilic attack: The nucleophile (water in this case) attacks the carbocation, forming the alcohol product.
SN2 (Substitution Nucleophilic Bimolecular)
Favored for primary halogenoalkanes and in polar aprotic solvents.
Involves a one-step concerted process:
1. Nucleophilic attack: The nucleophile attacks the carbon atom bearing the halogen, simultaneously displacing the halide ion.
Test for Halogenoalkanes:
The reaction of halogenoalkanes with silver nitrate in ethanol provides a way to distinguish between primary, secondary, and tertiary halogenoalkanes based on the rate of precipitation of a silver halide.
Primary halogenoalkanes react very slowly.
Secondary halogenoalkanes react at a moderate rate.
Tertiary halogenoalkanes react quickly.
Note: The specific mechanism for samples E, F, and G can't be determined without knowing their structures.