The compound CH₃OCH₂CH₂CH₂CH₂Br undergoes a solvolysis reaction in aqueous ethanol solution.Which of the following is evidence that a neighboring group effect is occurring?

Question

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Choice A shows evidence of a neighboring group effect, as the compound with the sulfur neighboring group (CH₃) reacts more slowly than the compound with the oxygen neighboring group (CH₃O). This suggests that the neighboring group is affecting the reactivity of the molecule, as expected in a neighboring group participation mechanism. Choices B, C, and D do not necessarily provide evidence of a neighboring group effect. The fact that the reaction is faster at higher concentrations of water (choice B) could be explained by other factors, such as increased solubility of the reactant or changes in the solvent environment. The reaction being first order (choice C) could also be consistent with other types of mechanisms. Lastly, the formation of HBr (choice D) is expected from the breaking of the carbon-bromine bond, but does not provide specific evidence of a neighboring group effect.

The Compound CH3OCH2CH2CH2CH2Br Undergoes a Solvolysis Reaction in Aqueous Ethanol

The Compound CH₃OCH₂CH₂CH₂CH₂Br Undergoes a Solvolysis Reaction in Aqueous Ethanol