Which of these alkyl halides cannot be used to prepare amines using Gabriel synthesis?
A) 1-bromopentane
B) 1-bromo-3-methylbutane
C) 2-bromo-3-methylpentane
D) 1-bromo-2,3-dimethylbutane
E) 2-bromo-2,3-dimethylbutane

Question

Quizplus · Accepted Answer

Gabriel synthesis involves nucleophilic substitution, which is hindered by steric effects. 2-bromo-2,3-dimethylbutane is a tertiary alkyl halide, which is too sterically hindered for the reaction to proceed effectively.

Which of These Alkyl Halides Cannot Be Used to Prepare