Reaction Mechanism of Tert-Butyl Bromide with Sodium Hydroxide

Medium Organic Chemistry Nucleophilic Substitution And Elimination Reactions

A chemist is investigating the reaction mechanism of a particular alkyl halide, 2-bromo-2-methylpropane (tert-butyl bromide). The chemist reacts tert-butyl bromide with sodium hydroxide (NaOH) in a suitable solvent and notes the formation of an alkene. Considering the structure of tert-butyl bromide and the nature of NaOH, which type of reaction primarily takes place: nucleophilic substitution or elimination?

Nucleophilic substitution through an SN2 mechanism.

Nucleophilic substitution through an SN1 mechanism.

Elimination through an E2 mechanism.

Elimination through an E1 mechanism.

Hint

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