Which of the following haloalkanes undergoes nucleophilic substitution via the mechanism at the highest rate?
Answer and explanation
Correct answer: A.
- Step 1: The reaction rate is governed by the stability of the carbocation intermediate formed in the rate-determining step.
- Step 2: Carbocation stability follows the order: .
- Step 3: Tert-butyl chloride, , forms a highly stable tertiary carbocation through nine hyperconjugative hydrogens and three methyl groups, reacting fastest.
Answer
.
Why not the others: reacts fastest via due to minimal steric hindrance; primary and secondary chlorides react much slower via .
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