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S(N)2 reaction will be fastest in:...

`S_(N)2` reaction will be fastest in:

A

`CH_(3)Br`

B

`CH_(3)Cl`

C

`CH_(3)CH_(2)Cl`

D

`(CH_(3))_(2)CHCl`

Text Solution

AI Generated Solution

The correct Answer is:
To determine which compound will undergo an \( S_N2 \) reaction the fastest, we need to consider two main factors: steric hindrance and the quality of the leaving group. The \( S_N2 \) mechanism involves a nucleophile attacking a carbon atom from the opposite side of the leaving group, leading to a transition state. Here's how we can analyze the options step by step: ### Step 1: Understand the \( S_N2 \) Mechanism The \( S_N2 \) reaction is characterized by a single concerted step where the nucleophile attacks the carbon atom while the leaving group departs. The reaction rate depends on: - The steric hindrance around the carbon atom (less steric hindrance leads to faster reactions). - The ability of the leaving group to depart (better leaving groups lead to faster reactions). ### Step 2: Evaluate Steric Hindrance - **Methyl carbon** (no alkyl groups attached) has the least steric hindrance. - **Primary carbon** (one alkyl group attached) has moderate steric hindrance. - **Secondary carbon** (two alkyl groups attached) has more steric hindrance. - **Tertiary carbon** (three alkyl groups attached) has the most steric hindrance and does not undergo \( S_N2 \) reactions effectively. ### Step 3: Assess the Leaving Group Common leaving groups in \( S_N2 \) reactions include: - Bromide (Br\(^-\)) - Chloride (Cl\(^-\)) - Iodide (I\(^-\)) Among these, bromide is generally a better leaving group than chloride due to its larger size and the stability of the bromide ion. ### Step 4: Analyze the Given Options Let’s analyze the options provided in the question: 1. **Option A**: Methyl halide (e.g., CH\(_3\)Br) 2. **Option B**: Primary halide (e.g., CH\(_3\)CH\(_2\)Br) 3. **Option C**: Secondary halide (e.g., CH\(_3\)CH(Br)CH\(_2\)CH\(_3\)) 4. **Option D**: Tertiary halide (e.g., (CH\(_3\))\(_3\)CBr) - **Option A** (Methyl halide) has no steric hindrance and a good leaving group (Br\(^-\)). - **Option B** (Primary halide) has low steric hindrance and a good leaving group (Br\(^-\)). - **Option C** (Secondary halide) has more steric hindrance and a good leaving group (Br\(^-\)). - **Option D** (Tertiary halide) has the highest steric hindrance and does not favor \( S_N2 \). ### Step 5: Conclusion Based on the analysis, **Option A** (Methyl halide with Br\(^-\)) will undergo the \( S_N2 \) reaction the fastest due to minimal steric hindrance and the presence of a good leaving group. ### Final Answer The \( S_N2 \) reaction will be fastest in **Option A** (Methyl halide with Br\(^-\)). ---
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