Question:medium

With reference to the two statements Assertion and Reason, choose the correct option.
• [Assertion:] The order of reactivity towards $\text{S}_{\text{N}}1$ reaction is: $\text{C}_6\text{H}_5\text{CH}_2\text{Br} > (\text{CH}_3)_2\text{CH-Br} > \text{CH}_3-\text{CH}_2\text{Br}$
• [Reason:] Among the given 3 compounds, the Benzyl carbocation formed is the most stable while Isopropyl carbocation is the least stable one

Show Hint

$\text{S}_{\text{N}}1$ reactivity is always determined by carbocation stability. Since the benzyl carbocation is resonance-stabilized, it is exceptionally stable, allowing benzyl bromide to react faster than secondary or primary aliphatic halides.
Updated On: May 20, 2026
  • Both Assertion and Reason are correct and Reason is the correct explanation of Assertion
  • Both Assertion and Reason are correct but Reason is not the correct explanation of Assertion
  • Reason is correct but Assertion is wrong
  • Assertion is correct but Reason is wrong
Show Solution

The Correct Option is A

Solution and Explanation

Understanding the Concept: An $\text{S}_{\text{N}}1$ nucleophilic substitution mechanism proceeds via a two-step pathway where the rate-determining step involves the heterolytic cleavage of the carbon-leaving group bond to form a carbocation intermediate. The relative reactivity of alkyl halides under $\text{S}_{\text{N}}1$ conditions depends directly on the stability of the resulting carbocation intermediate.
Step 1: Evaluate the assertion by comparing the carbocation stability of the structures.
Let's look at the carbocations generated by each compound:
$\text{C}_6\text{H}_5\text{CH}_2\text{Br} \rightarrow \text{C}_6\text{H}_5\text{CH}_2^+$ (Benzyl carbocation, highly stabilized by resonance delocalization across the aromatic ring $\pi$-system).
$(\text{CH}_3)_2\text{CH-Br} \rightarrow (\text{CH}_3)_2\text{CH}^+$ (Isopropyl carbocation, a secondary carbocation stabilized by $+I$ inductive effects and 6 hyperconjugation structures).
$\text{CH}_3\text{CH}_2\text{Br} \rightarrow \text{CH}_3\text{CH}_2^+$ (Ethyl carbocation, a primary carbocation with minimal stabilization).
The stability order is: $\text{Benzyl}>\text{Isopropyl}>\text{Ethyl}$. This matches the stated reactivity trend, confirming the assertion is correct.
Step 2: Evaluate the reason and its logical link to the assertion.
The reason states that the benzyl carbocation is the most stable and the isopropyl carbocation is the least stable among the three compounds. This stability order explains why benzyl bromide undergoes substitution fastest and ethyl bromide slowest. Therefore, both statements are correct, and the reason provides the correct explanation for the assertion.
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