JEE Main 2020 · 3 September · morning · Single correct · +4 / −1

The mechanism of S N 1 reaction is given as : R-X → R⊕ X⊖ → R⊕ ∥ X⊖ →(Y⊖) R-Y + X⊖
A student writes general characteristics based on the given mechanism as :
(a) The reaction is favoured by weak nucleophiles.
(b) R⁺ would be easily formed if the substituents are bulky.
(c) The reaction is accompanied by racemization.
(d) The reaction is favoured by non-polar solvents.

  1. (a) (a) and (b)
  2. (b) (a), (b) and (c)
  3. (c) (a) and (c)
  4. (d) (b) and (d)
Answer and solution

Answer (b) (a), (b) and (c)

Solution

Chemistry ma’am · 2 steps

Read the mechanism: a bare carbocation forms first, so ask what helps it form and what happens to it next.

  1. Slow step. In S_N1 the slow step is R-X breaking into R⁺ and X⁻. The nucleophile Y⁻ joins only after that, so it plays no part in the rate.
    StatementWhat the mechanism saysVerdict
    (a) Weak nucleophiles favour itY⁻ is not in the slow step. A weak nucleophile does not slow S_N1, but it does slow the competing S_N2.True
    (b) Bulky groups help R⁺ formBulky alkyl groups push electrons into R⁺ and are crowded less once the carbon turns planar (sp²), so ionisation is easier.True
    (c) Racemization occursR⁺ is planar, so Y⁻ can attack from either face and both enantiomers form.True
    (d) Non-polar solvents favour itThe ion pair and the solvent-separated ion pair need a polar (protic) solvent to stabilise the ions.False
  2. So. Statements (a), (b) and (c) are correct and (d) is wrong, which is option (b).

The idea to keep. For S_N1, think carbocation: stable R⁺ (bulky, tertiary), polar protic solvent, nucleophile strength irrelevant, and a planar ion that gives racemization.

Answer from the NTA final answer key. Solution by PrepWiser.

Study Halogen Derivatives — Haloalkanes & Haloarenes

Asked about 120 times in JEE Main since 2020. This question is from 2020.