CAIE A-Level Chemistry AS 15.1.6 Sn2 Sn1 Trends in Halogenoalkanes Questions

Practise predicting SN1 or SN2 behaviour from primary, secondary and tertiary halogenoalkane structure, steric hindrance and carbocation stability.

Exam points

predict primary halogenoalkanes favour SN2 because steric hindrance to direct attack is low
predict tertiary halogenoalkanes favour SN1 because their carbocations are stabilised by alkyl groups
treat secondary halogenoalkanes as condition-dependent and justify the dominant pathway

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Which statement describes what happens when 2-chloro-2-methylpropane is warmed with NaOH(aq) ?

This secondary halogenoalkane reacts by a mixture of an $\mathrm{S}_{\mathrm{N}} 1$ and an $\mathrm{S}_{\mathrm{N}} 2$ mechanism.

This secondary halogenoalkane reacts only by an $\mathrm{S}_{\mathrm{N}} 2$ mechanism.

This tertiary halogenoalkane reacts mostly by an $\mathrm{S}_{\mathrm{N}} 1$ mechanism.

This tertiary halogenoalkane does not react with hydroxide ions under these conditions.

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