Final answer:
2-chloro-2,3-dimethylbutane cannot be used in Gabriel synthesis to prepare amines because it is a tertiary alkyl halide, which is not reactive in this synthesis due to steric hindrance and the preference for elimination reactions.
Step-by-step explanation:
The Gabriel synthesis is a method used to synthesize primary amines from primary alkyl halides. This reaction is not compatible with secondary or tertiary alkyl halides because these would lead to elimination reactions or be too sterically hindered to undergo the necessary nucleophilic substitution steps. Looking at the provided options, 2-chloro-2,3-dimethylbutane cannot be used to prepare amines using Gabriel synthesis because it is a tertiary alkyl halide. The halogen atom is bonded to a carbon atom that is itself directly bonded to three other carbon atoms, making nucleophilic substitution highly unlikely.