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QUESTION

# Why do primary alkyl halides generally undergo SN2 mechanisms?

Primary alkyl halides generally undergo "S"_N2 mechanisms because (a) 1° substrates have little steric hindrance to nucleophilic attack and (b) 1° carbocations are relatively unstable.

Steric Hindrance

As more alkyl groups are added to the α carbon atom, the substrate becomes less susceptible to "S"_N2 attack

A 1° alkyl is sterically unhindered, so an "S"_N2 reaction is likely.

Instability of 1° Carbocations

Alkyl groups release electrons by inductive and hyperconjugation effects, so they can stabilize a positive charge on the α carbon.

A 1° alkyl halide has only one alkyl group, so it is relatively unstable. It is unlikely to form a 1° carbocation in an "S"_N1 reaction.

Instead it will take the lower-energy "S"_N2 path, in which the nucleophile "kicks out" the halide leaving group.

This avoids the formation of the unstable carbocation.