Predict the compound which will undergo solvolysis (aqueous ethanol) more rapidly.

Options

A. `CH_(3)-(CH_(2))_(2)-CH-Cl`
B. `H_(3)C-underset(CH_(3))underset(|)overset(Cl)overset(|)C-CH_(3)`
C. `H_(5)C_(6)-underset(CH_(3))underset(|)overset(Cl)overset(|)C-CH_(3)`
D. `H_(3)C-CH_(2)-overset(Cl)overset(|)CH-CH_(3)`

Answer

To predict which compound will undergo solvolysis more rapidly in aqueous ethanol, we need to analyze the stability of the carbocations formed during the reaction. The solvolysis reaction follows an SN1 mechanism, which involves two main steps: the formation of a carbocation and the subsequent nucleophilic attack by the solvent (ethanol in this case).

### Step-by-Step Solution:

1. **Identify the Compounds**:
Let's assume we have two alkyl halides to compare, for example, 1-bromopropane (R-CH2-CH2-CH2-Br) and tert-butyl bromide (R-C(CH3)3-Br).

2. **Understand the SN1 Mechanism**:
The SN1 mechanism involves two steps:
- **Step 1**: Formation of a carbocation by the departure of the leaving group (Br in this case).
- **Step 2**: Nucleophilic attack by the solvent (ethanol).

3. **Carbocation Stability**:
The rate of solvolysis is primarily determined by the stability of the carbocation formed in the first step. The more stable the carbocation, the faster the reaction will proceed. Carbocation stability increases in the following order:
- Methyl < Primary < Secondary < Tertiary
- Additionally, resonance can stabilize carbocations significantly.

4. **Analyze the Carbocations**:
- For 1-bromopropane, the carbocation formed is a primary carbocation (R-CH2-CH2-CH2^+), which is relatively unstable.
- For tert-butyl bromide, the carbocation formed is a tertiary carbocation (R-C^+(CH3)3), which is much more stable due to hyperconjugation and inductive effects from the three methyl groups.

5. **Conclusion**:
Since tert-butyl bromide forms a more stable carbocation compared to 1-bromopropane, it will undergo solvolysis more rapidly in aqueous ethanol.

### Final Answer:
**Tert-butyl bromide will undergo solvolysis more rapidly than 1-bromopropane due to the formation of a more stable tertiary carbocation.**