Good leaving groups are weak bases. Allylic/benzylic enhance SN1. Aryl/vinyl are unreactive.
Frequently Asked Questions
What is the primary difference between SN1 and SN2 reactions?▾
SN1 is a two-step unimolecular reaction involving a carbocation intermediate, leading to partial racemization. SN2 is a one-step bimolecular reaction involving a transition state, resulting in complete inversion of configuration.
How does the structure of the alkyl halide affect its reactivity in SN1 and SN2 reactions?▾
For SN1, reactivity increases with carbocation stability (3° > 2° > 1°). For SN2, reactivity decreases with steric hindrance around the reaction center (1° > 2° > 3°).
What role do solvents play in nucleophilic substitution reactions?▾
Polar protic solvents (like water, alcohol) stabilize carbocations, favoring SN1 reactions. Polar aprotic solvents (like DMSO, DMF, acetone) do not solvate nucleophiles strongly, making them more reactive and favoring SN2 reactions.
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