Question

Select the member of each pair that undergoes \(S_{N} 1\) solvolysis in aqueous ethanol more rapidly.

Short answer

#Short Answer# To determine which member of each pair undergoes \(S_{N}1\) solvolysis more rapidly in aqueous ethanol, first identify the leaving group in each compound. Next, determine and evaluate the stability of the carbocation intermediate generated when the leaving group departs. Carbocation stability is influenced by degree (primary, secondary, or tertiary), resonance, and inductive effects from electron-withdrawing groups. Compare the stability of the carbocation intermediates within each pair; the compound with the more stable carbocation will undergo \(S_{N}1\) solvolysis more rapidly.

Step-by-step solution

Write down the given pairs of compounds

First, we need to list the given pairs of compounds, which will undergo \(S_{N}1\) solvolysis. (Note: In this solution, we assume that the pairs of compounds are not provided. If you could provide the pairs, we can give a more specific step by step solution for each pair). Pair A: Compound 1A and Compound 2A Pair B: Compound 1B and Compound 2B Pair C: Compound 1C and Compound 2C ... and so on.

Identify the leaving group in each compound

For each compound, identify the leaving group that will depart from the molecule during \(S_{N}1\) solvolysis. Good leaving groups are groups that can stabilize negative charge well. Common leaving groups are halogens (like Cl, Br, or I) or other electron-withdrawing groups.

Determine the carbocation intermediate for each compound

Next, imagine the leaving group departing from each compound and forming a carbocation intermediate. Draw the carbocation structures to visualize how the positive charge is distributed within the molecule.

Evaluate the stability of the carbocation intermediates

Now, evaluate the stability of each carbocation intermediate. The stability of carbocation is determined by several factors: 1. Degree: Primary (R-CH2+) < Secondary (R2-CH+) < Tertiary (R3-C+) 2. Resonance: Carbocations stabilized by resonance are more stable 3. Inductive effect: An electron-withdrawing group can stabilize a carbocation via induction

Compare the stability and reactivity of each pair

Compare the stability of the carbocation intermediates in each pair. The more stable the carbocation intermediate, the faster the compound will undergo \(S_{N}1\) solvolysis. For example: - If the carbocation generated from Compound 1A is more stable than the one generated from Compound 2A, then Compound 1A undergoes \(S_{N}1\) solvolysis more rapidly than Compound 2A. - If the carbocation generated from Compound 1B is less stable than the one generated from Compound 2B, then Compound 2B undergoes \(S_{N}1\) solvolysis more rapidly than Compound 1B. Repeat this step for the remaining pairs.