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The increasing order of reactivity of th...

The increasing order of reactivity of the following halides for the `S_(N)1` reaction is
I.`CH_(3)CH(CI)CH_(2)CH_(3)`
`II . CH_(3)CH_(2)CH_(2)Cl`
III. `p. -H_(3)CO-C_(6)H_(4)-CH_(2)Cl`

A

(a) II < I < III

B

(b) I < III < II

C

(c) II < III < I

D

(d) III < II < I

Text Solution

AI Generated Solution

The correct Answer is:
To determine the increasing order of reactivity of the given halides for the SN1 reaction, we first need to analyze the stability of the carbocations that would form when each halide undergoes the SN1 reaction. ### Step 1: Identify the structure of each halide and the type of carbocation formed. 1. **Compound I: CH3CH(CI)CH2CH3** - This compound has a chlorine atom attached to a secondary carbon (the carbon bonded to the chlorine is connected to two other carbons). - Upon leaving, it forms a **secondary carbocation**. 2. **Compound II: CH3CH2CH2Cl** - This compound has a chlorine atom attached to a primary carbon (the carbon bonded to the chlorine is connected to only one other carbon). - Upon leaving, it forms a **primary carbocation**. 3. **Compound III: p-H3CO-C6H4-CH2Cl** - This compound has a chlorine atom attached to a benzylic position (the carbon bonded to the chlorine is connected to a benzene ring). - Upon leaving, it forms a **benzylic carbocation**, which is stabilized by resonance. ### Step 2: Compare the stability of the carbocations. - **Primary carbocation (Compound II)**: Least stable due to lack of alkyl groups to stabilize the positive charge. - **Secondary carbocation (Compound I)**: More stable than primary due to the presence of one alkyl group. - **Benzylic carbocation (Compound III)**: Most stable due to resonance stabilization from the adjacent benzene ring. ### Step 3: Determine the order of reactivity based on carbocation stability. The reactivity in SN1 reactions increases with the stability of the carbocation formed: - **Compound II (Primary)** < **Compound I (Secondary)** < **Compound III (Benzylic)** ### Conclusion: Write the increasing order of reactivity. Thus, the increasing order of reactivity of the halides for the SN1 reaction is: **II < I < III** ### Final Answer: The increasing order of reactivity of the halides for the SN1 reaction is: **II < I < III** ---
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