Nucleophilic Substitution Reaction of Tert-Butyl Bromide

Very Hard Organic Chemistry Nucleophilic Substitution And Elimination Reactions

In organic chemistry, the mechanism of nucleophilic substitution illustrates the fundamental differences between S_N1 and S_N2 reactions. Consider the compound 2-bromo-2-methylpropane (tert-butyl bromide) being subjected to nucleophilic attack by a hydroxide ion (OH^-) in a polar protic solvent. Given that 2-bromo-2-methylpropane is a tertiary alkyl halide, which of the following statements regarding the reaction mechanism and the expected products is correct?

The reaction will proceed through a concerted, single-step mechanism, resulting in the formation of tert-butanol.

The reaction will proceed via a two-step mechanism, leading to both tert-butanol and bromide ions being formed.

The reaction is unfavorable due to steric hindrance, and no substitution product will be formed.

The reaction is likely to undergo a S<sub>N</sub>1 mechanism, ultimately producing tert-butanol as the major product.

Hint

Submitted4.3K

Correct3.4K

% Correct79%