Isopropyl chloride undergoes hydrolysis by :

Options

A. `S_(N)` 1 mechanism
B. `S_(N)` 2 mechanism
C. `S_(N) 1 and S_(N)` 2 mechanism
D. neither `S_(N)` 1 nor `S_(N)` 2 mechanism

Answer

To determine how isopropyl chloride undergoes hydrolysis, we need to analyze the mechanisms involved. Here’s a step-by-step solution:

### Step 1: Identify Isopropyl Chloride
Isopropyl chloride is a haloalkane with the chemical formula \( \text{C}_3\text{H}_7\text{Cl} \) or \( \text{CH}_3\text{CHClCH}_3 \).

**Hint:** Recognize the structure of isopropyl chloride to understand its reactivity.

### Step 2: Understand Hydrolysis Mechanisms
Hydrolysis can occur through two main mechanisms: SN1 and SN2.

- **SN1 Mechanism**: This is a unimolecular nucleophilic substitution that involves two steps:
1. Formation of a carbocation after the leaving group departs.
2. Nucleophilic attack on the carbocation.

- **SN2 Mechanism**: This is a bimolecular nucleophilic substitution that occurs in one step:
1. The nucleophile attacks the substrate as the leaving group departs, forming a transition state.

**Hint:** Differentiate between SN1 and SN2 based on the number of steps and the order of kinetics.

### Step 3: Analyze the Reaction Pathways
1. **SN1 Pathway**:
- The chloride ion (Cl-) leaves, forming a secondary carbocation.
- The nucleophile (usually water, \( \text{H}_2\text{O} \)) then attacks the carbocation to form isopropyl alcohol (\( \text{CH}_3\text{CHOHCH}_3 \)).

2. **SN2 Pathway**:
- The nucleophile (water) attacks the carbon atom bonded to the chlorine while the chlorine leaves simultaneously.
- This also leads to the formation of isopropyl alcohol.

**Hint:** Visualize the steps to see how the nucleophile interacts with the substrate.

### Step 4: Determine the Rate of Reaction
- In the **SN1 mechanism**, the rate of reaction depends only on the concentration of isopropyl chloride (the substrate).
- In the **SN2 mechanism**, the rate depends on the concentration of both isopropyl chloride and the nucleophile.

**Hint:** Recall that SN1 is first-order and SN2 is second-order in terms of kinetics.

### Step 5: Conclusion
Isopropyl chloride can undergo hydrolysis through both SN1 and SN2 mechanisms, resulting in the same product (isopropyl alcohol). Therefore, the correct answer is that isopropyl chloride undergoes hydrolysis by both mechanisms.

**Final Answer:** Isopropyl chloride undergoes hydrolysis by both SN1 and SN2 mechanisms.

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